Merge branch 'Infisical:main' into main

backend/src/services/app-connection/app-connection-enums.ts

@@ -36,7 +36,8 @@ export enum AppConnection {
   Supabase = "supabase",
   DigitalOcean = "digital-ocean",
   Netlify = "netlify",
-  Okta = "okta"
+  Okta = "okta",
+  Redis = "redis"
 }
 
 export enum AWSRegion {

backend/src/services/app-connection/app-connection-fns.ts

@@ -111,6 +111,7 @@ import { getNetlifyConnectionListItem, validateNetlifyConnectionCredentials } fr
 import { getOktaConnectionListItem, OktaConnectionMethod, validateOktaConnectionCredentials } from "./okta";
 import { getPostgresConnectionListItem, PostgresConnectionMethod } from "./postgres";
 import { getRailwayConnectionListItem, validateRailwayConnectionCredentials } from "./railway";
+import { getRedisConnectionListItem, RedisConnectionMethod, validateRedisConnectionCredentials } from "./redis";
 import { RenderConnectionMethod } from "./render/render-connection-enums";
 import { getRenderConnectionListItem, validateRenderConnectionCredentials } from "./render/render-connection-fns";
 import {
@@ -150,7 +151,12 @@ const SECRET_SCANNING_APP_CONNECTION_MAP = Object.fromEntries(
 );
 
 // scott: ideally this would be derived from a utilized map like the above
-const PKI_APP_CONNECTIONS = [AppConnection.AWS, AppConnection.Cloudflare, AppConnection.AzureADCS];
+const PKI_APP_CONNECTIONS = [
+  AppConnection.AWS,
+  AppConnection.Cloudflare,
+  AppConnection.AzureADCS,
+  AppConnection.AzureKeyVault
+];
 
 export const listAppConnectionOptions = (projectType?: ProjectType) => {
   return [
@@ -191,7 +197,8 @@ export const listAppConnectionOptions = (projectType?: ProjectType) => {
     getSupabaseConnectionListItem(),
     getDigitalOceanConnectionListItem(),
     getNetlifyConnectionListItem(),
-    getOktaConnectionListItem()
+    getOktaConnectionListItem(),
+    getRedisConnectionListItem()
   ]
     .filter((option) => {
       switch (projectType) {
@@ -317,7 +324,8 @@ export const validateAppConnectionCredentials = async (
     [AppConnection.Supabase]: validateSupabaseConnectionCredentials as TAppConnectionCredentialsValidator,
     [AppConnection.DigitalOcean]: validateDigitalOceanConnectionCredentials as TAppConnectionCredentialsValidator,
     [AppConnection.Okta]: validateOktaConnectionCredentials as TAppConnectionCredentialsValidator,
-    [AppConnection.Netlify]: validateNetlifyConnectionCredentials as TAppConnectionCredentialsValidator
+    [AppConnection.Netlify]: validateNetlifyConnectionCredentials as TAppConnectionCredentialsValidator,
+    [AppConnection.Redis]: validateRedisConnectionCredentials as TAppConnectionCredentialsValidator
   };
 
   return VALIDATE_APP_CONNECTION_CREDENTIALS_MAP[appConnection.app](appConnection, gatewayService, gatewayV2Service);
@@ -364,6 +372,7 @@ export const getAppConnectionMethodName = (method: TAppConnection["method"]) =>
     case MySqlConnectionMethod.UsernameAndPassword:
     case OracleDBConnectionMethod.UsernameAndPassword:
     case AzureADCSConnectionMethod.UsernamePassword:
+    case RedisConnectionMethod.UsernameAndPassword:
       return "Username & Password";
     case WindmillConnectionMethod.AccessToken:
     case HCVaultConnectionMethod.AccessToken:
@@ -451,7 +460,8 @@ export const TRANSITION_CONNECTION_CREDENTIALS_TO_PLATFORM: Record<
   [AppConnection.Supabase]: platformManagedCredentialsNotSupported,
   [AppConnection.DigitalOcean]: platformManagedCredentialsNotSupported,
   [AppConnection.Netlify]: platformManagedCredentialsNotSupported,
-  [AppConnection.Okta]: platformManagedCredentialsNotSupported
+  [AppConnection.Okta]: platformManagedCredentialsNotSupported,
+  [AppConnection.Redis]: platformManagedCredentialsNotSupported
 };
 
 export const enterpriseAppCheck = async (

backend/src/services/app-connection/app-connection-maps.ts

@@ -38,7 +38,8 @@ export const APP_CONNECTION_NAME_MAP: Record<AppConnection, string> = {
   [AppConnection.Supabase]: "Supabase",
   [AppConnection.DigitalOcean]: "DigitalOcean App Platform",
   [AppConnection.Netlify]: "Netlify",
-  [AppConnection.Okta]: "Okta"
+  [AppConnection.Okta]: "Okta",
+  [AppConnection.Redis]: "Redis"
 };
 
 export const APP_CONNECTION_PLAN_MAP: Record<AppConnection, AppConnectionPlanType> = {
@@ -79,5 +80,6 @@ export const APP_CONNECTION_PLAN_MAP: Record<AppConnection, AppConnectionPlanTyp
   [AppConnection.Supabase]: AppConnectionPlanType.Regular,
   [AppConnection.DigitalOcean]: AppConnectionPlanType.Regular,
   [AppConnection.Netlify]: AppConnectionPlanType.Regular,
-  [AppConnection.Okta]: AppConnectionPlanType.Regular
+  [AppConnection.Okta]: AppConnectionPlanType.Regular,
+  [AppConnection.Redis]: AppConnectionPlanType.Regular
 };

backend/src/services/app-connection/app-connection-service.ts

@@ -99,6 +99,7 @@ import { oktaConnectionService } from "./okta/okta-connection-service";
 import { ValidatePostgresConnectionCredentialsSchema } from "./postgres";
 import { ValidateRailwayConnectionCredentialsSchema } from "./railway";
 import { railwayConnectionService } from "./railway/railway-connection-service";
+import { ValidateRedisConnectionCredentialsSchema } from "./redis";
 import { ValidateRenderConnectionCredentialsSchema } from "./render/render-connection-schema";
 import { renderConnectionService } from "./render/render-connection-service";
 import { ValidateSupabaseConnectionCredentialsSchema } from "./supabase";
@@ -166,7 +167,8 @@ const VALIDATE_APP_CONNECTION_CREDENTIALS_MAP: Record<AppConnection, TValidateAp
   [AppConnection.Supabase]: ValidateSupabaseConnectionCredentialsSchema,
   [AppConnection.DigitalOcean]: ValidateDigitalOceanConnectionCredentialsSchema,
   [AppConnection.Netlify]: ValidateNetlifyConnectionCredentialsSchema,
-  [AppConnection.Okta]: ValidateOktaConnectionCredentialsSchema
+  [AppConnection.Okta]: ValidateOktaConnectionCredentialsSchema,
+  [AppConnection.Redis]: ValidateRedisConnectionCredentialsSchema
 };
 
 export const appConnectionServiceFactory = ({
@@ -266,9 +268,9 @@ export const appConnectionServiceFactory = ({
       const { permission } = await permissionService.getOrgPermission(
         actor.type,
         actor.id,
-        actor.orgId,
+        appConnection.orgId,
         actor.authMethod,
-        appConnection.orgId
+        actor.orgId
       );
 
       ForbiddenError.from(permission).throwUnlessCan(
@@ -316,9 +318,9 @@ export const appConnectionServiceFactory = ({
       const { permission } = await permissionService.getOrgPermission(
         actor.type,
         actor.id,
-        actor.orgId,
+        appConnection.orgId,
         actor.authMethod,
-        appConnection.orgId
+        actor.orgId
       );
 
       ForbiddenError.from(permission).throwUnlessCan(
@@ -475,9 +477,9 @@ export const appConnectionServiceFactory = ({
     const { permission: orgPermission } = await permissionService.getOrgPermission(
       actor.type,
       actor.id,
-      actor.orgId,
+      appConnection.orgId,
       actor.authMethod,
-      appConnection.orgId
+      actor.orgId
     );
 
     if (appConnection.projectId) {
@@ -633,9 +635,9 @@ export const appConnectionServiceFactory = ({
       const { permission } = await permissionService.getOrgPermission(
         actor.type,
         actor.id,
-        actor.orgId,
+        appConnection.orgId,
         actor.authMethod,
-        appConnection.orgId
+        actor.orgId
       );
 
       ForbiddenError.from(permission).throwUnlessCan(
@@ -803,9 +805,9 @@ export const appConnectionServiceFactory = ({
     const { permission } = await permissionService.getOrgPermission(
       actor.type,
       actor.id,
-      actor.orgId,
+      appConnection.orgId,
       actor.authMethod,
-      appConnection.orgId
+      actor.orgId
     );
 
     ForbiddenError.from(permission).throwUnlessCan(

backend/src/services/app-connection/app-connection-types.ts

@@ -179,6 +179,12 @@ import {
   TRailwayConnectionInput,
   TValidateRailwayConnectionCredentialsSchema
 } from "./railway";
+import {
+  TRedisConnection,
+  TRedisConnectionConfig,
+  TRedisConnectionInput,
+  TValidateRedisConnectionCredentialsSchema
+} from "./redis";
 import {
   TRenderConnection,
   TRenderConnectionConfig,
@@ -261,6 +267,7 @@ export type TAppConnection = { id: string } & (
   | TDigitalOceanConnection
   | TNetlifyConnection
   | TOktaConnection
+  | TRedisConnection
 );
 
 export type TAppConnectionRaw = NonNullable<Awaited<ReturnType<TAppConnectionDALFactory["findById"]>>>;
@@ -306,6 +313,7 @@ export type TAppConnectionInput = { id: string } & (
   | TDigitalOceanConnectionInput
   | TNetlifyConnectionInput
   | TOktaConnectionInput
+  | TRedisConnectionInput
 );
 
 export type TSqlConnectionInput =
@@ -368,7 +376,8 @@ export type TAppConnectionConfig =
   | TSupabaseConnectionConfig
   | TDigitalOceanConnectionConfig
   | TNetlifyConnectionConfig
-  | TOktaConnectionConfig;
+  | TOktaConnectionConfig
+  | TRedisConnectionConfig;
 
 export type TValidateAppConnectionCredentialsSchema =
   | TValidateAwsConnectionCredentialsSchema
@@ -408,7 +417,8 @@ export type TValidateAppConnectionCredentialsSchema =
   | TValidateSupabaseConnectionCredentialsSchema
   | TValidateDigitalOceanCredentialsSchema
   | TValidateNetlifyConnectionCredentialsSchema
-  | TValidateOktaConnectionCredentialsSchema;
+  | TValidateOktaConnectionCredentialsSchema
+  | TValidateRedisConnectionCredentialsSchema;
 
 export type TListAwsConnectionKmsKeys = {
   connectionId: string;

backend/src/services/app-connection/heroku/heroku-connection-fns.ts

@@ -22,13 +22,13 @@ interface HerokuOAuthTokenResponse {
 }
 
 export const getHerokuConnectionListItem = () => {
-  const { CLIENT_ID_HEROKU } = getConfig();
+  const { INF_APP_CONNECTION_HEROKU_OAUTH_CLIENT_ID } = getConfig();
 
   return {
     name: "Heroku" as const,
     app: AppConnection.Heroku as const,
     methods: Object.values(HerokuConnectionMethod) as [HerokuConnectionMethod.AuthToken, HerokuConnectionMethod.OAuth],
-    oauthClientId: CLIENT_ID_HEROKU
+    oauthClientId: INF_APP_CONNECTION_HEROKU_OAUTH_CLIENT_ID
   };
 };
 
@@ -40,12 +40,12 @@ export const refreshHerokuToken = async (
   appConnectionDAL: Pick<TAppConnectionDALFactory, "updateById">,
   kmsService: Pick<TKmsServiceFactory, "createCipherPairWithDataKey">
 ): Promise<string> => {
-  const { CLIENT_SECRET_HEROKU } = getConfig();
+  const { INF_APP_CONNECTION_HEROKU_OAUTH_CLIENT_SECRET } = getConfig();
 
   const payload = {
     grant_type: "refresh_token",
     refresh_token: refreshToken,
-    client_secret: CLIENT_SECRET_HEROKU
+    client_secret: INF_APP_CONNECTION_HEROKU_OAUTH_CLIENT_SECRET
   };
 
   const { data } = await request.post<{ access_token: string; expires_in: number }>(
@@ -75,7 +75,7 @@ export const refreshHerokuToken = async (
 };
 
 export const exchangeHerokuOAuthCode = async (code: string): Promise<HerokuOAuthTokenResponse> => {
-  const { CLIENT_SECRET_HEROKU } = getConfig();
+  const { INF_APP_CONNECTION_HEROKU_OAUTH_CLIENT_SECRET } = getConfig();
 
   try {
     const response = await request.post<HerokuOAuthTokenResponse>(
@@ -83,7 +83,7 @@ export const exchangeHerokuOAuthCode = async (code: string): Promise<HerokuOAuth
       {
         grant_type: "authorization_code",
         code,
-        client_secret: CLIENT_SECRET_HEROKU
+        client_secret: INF_APP_CONNECTION_HEROKU_OAUTH_CLIENT_SECRET
       },
       {
         headers: {

backend/src/services/app-connection/redis/index.ts

@@ -0,0 +1,4 @@
+export * from "./redis-connection-enums";
+export * from "./redis-connection-fns";
+export * from "./redis-connection-schemas";
+export * from "./redis-connection-types";

backend/src/services/app-connection/redis/redis-connection-enums.ts

@@ -0,0 +1,3 @@
+export enum RedisConnectionMethod {
+  UsernameAndPassword = "username-and-password"
+}

backend/src/services/app-connection/redis/redis-connection-fns.ts

@@ -0,0 +1,59 @@
+import Redis from "ioredis";
+
+import { verifyHostInputValidity } from "@app/ee/services/dynamic-secret/dynamic-secret-fns";
+import { BadRequestError } from "@app/lib/errors";
+import { AppConnection } from "@app/services/app-connection/app-connection-enums";
+
+import { RedisConnectionMethod } from "./redis-connection-enums";
+import { TRedisConnectionConfig } from "./redis-connection-types";
+
+export const getRedisConnectionListItem = () => {
+  return {
+    name: "Redis" as const,
+    app: AppConnection.Redis as const,
+    methods: Object.values(RedisConnectionMethod) as [RedisConnectionMethod.UsernameAndPassword],
+    supportsPlatformManagement: false as const
+  };
+};
+
+export const validateRedisConnectionCredentials = async (config: TRedisConnectionConfig) => {
+  const [hostIp] = await verifyHostInputValidity(config.credentials.host);
+
+  let connection: Redis | null = null;
+  try {
+    connection = new Redis({
+      username: config.credentials.username,
+      host: hostIp,
+      port: config.credentials.port,
+      password: config.credentials.password,
+      ...(config.credentials.sslEnabled && {
+        tls: {
+          rejectUnauthorized: config.credentials.sslRejectUnauthorized,
+          ca: config.credentials.sslCertificate
+        }
+      })
+    });
+
+    let result: string;
+    if (config.credentials.password) {
+      result = await connection.auth(config.credentials.username, config.credentials.password, () => {});
+    } else {
+      result = await connection.auth(config.credentials.username, () => {});
+    }
+
+    if (result !== "OK") {
+      throw new BadRequestError({ message: `Invalid credentials, Redis returned ${result} status` });
+    }
+
+    return config.credentials;
+  } catch (err) {
+    if (err instanceof BadRequestError) {
+      throw err;
+    }
+    throw new BadRequestError({
+      message: `Unable to validate connection: ${(err as Error)?.message || "verify credentials"}`
+    });
+  } finally {
+    if (connection) await connection.quit();
+  }
+};

backend/src/services/app-connection/redis/redis-connection-schemas.ts

@@ -0,0 +1,87 @@
+import z from "zod";
+
+import { AppConnections } from "@app/lib/api-docs";
+import {
+  BaseAppConnectionSchema,
+  GenericCreateAppConnectionFieldsSchema,
+  GenericUpdateAppConnectionFieldsSchema
+} from "@app/services/app-connection/app-connection-schemas";
+
+import { AppConnection } from "../app-connection-enums";
+import { RedisConnectionMethod } from "./redis-connection-enums";
+
+export const BaseRedisUsernameAndPasswordConnectionSchema = z.object({
+  host: z.string().toLowerCase().min(1),
+  port: z.coerce.number(),
+  username: z.string().min(1),
+  password: z.string().min(1).optional(),
+
+  sslRejectUnauthorized: z.boolean(),
+  sslEnabled: z.boolean(),
+  sslCertificate: z
+    .string()
+    .trim()
+    .transform((value) => value || undefined)
+    .optional()
+});
+
+export const RedisConnectionAccessTokenCredentialsSchema = BaseRedisUsernameAndPasswordConnectionSchema;
+
+const BaseRedisConnectionSchema = BaseAppConnectionSchema.extend({ app: z.literal(AppConnection.Redis) });
+
+export const RedisConnectionSchema = BaseRedisConnectionSchema.extend({
+  method: z.literal(RedisConnectionMethod.UsernameAndPassword),
+  credentials: RedisConnectionAccessTokenCredentialsSchema
+});
+
+export const SanitizedRedisConnectionSchema = z.discriminatedUnion("method", [
+  BaseRedisConnectionSchema.extend({
+    method: z.literal(RedisConnectionMethod.UsernameAndPassword),
+    credentials: RedisConnectionAccessTokenCredentialsSchema.pick({
+      host: true,
+      port: true,
+      username: true,
+      sslEnabled: true,
+      sslRejectUnauthorized: true,
+      sslCertificate: true
+    })
+  })
+]);
+
+export const ValidateRedisConnectionCredentialsSchema = z.discriminatedUnion("method", [
+  z.object({
+    method: z
+      .literal(RedisConnectionMethod.UsernameAndPassword)
+      .describe(AppConnections.CREATE(AppConnection.Redis).method),
+    credentials: RedisConnectionAccessTokenCredentialsSchema.describe(
+      AppConnections.CREATE(AppConnection.Redis).credentials
+    )
+  })
+]);
+
+export const CreateRedisConnectionSchema = ValidateRedisConnectionCredentialsSchema.and(
+  GenericCreateAppConnectionFieldsSchema(AppConnection.Redis, {
+    supportsPlatformManagedCredentials: false,
+    supportsGateways: false
+  })
+);
+
+export const UpdateRedisConnectionSchema = z
+  .object({
+    credentials: RedisConnectionAccessTokenCredentialsSchema.optional().describe(
+      AppConnections.UPDATE(AppConnection.Redis).credentials
+    )
+  })
+  .and(
+    GenericUpdateAppConnectionFieldsSchema(AppConnection.Redis, {
+      supportsPlatformManagedCredentials: false,
+      supportsGateways: false
+    })
+  );
+
+export const RedisConnectionListItemSchema = z.object({
+  name: z.literal("Redis"),
+  app: z.literal(AppConnection.Redis),
+  methods: z.nativeEnum(RedisConnectionMethod).array(),
+  supportsPlatformManagement: z.literal(false)
+});

backend/src/services/app-connection/redis/redis-connection-types.ts

@@ -0,0 +1,22 @@
+import z from "zod";
+
+import { DiscriminativePick } from "@app/lib/types";
+
+import { AppConnection } from "../app-connection-enums";
+import {
+  CreateRedisConnectionSchema,
+  RedisConnectionSchema,
+  ValidateRedisConnectionCredentialsSchema
+} from "./redis-connection-schemas";
+
+export type TRedisConnection = z.infer<typeof RedisConnectionSchema>;
+
+export type TRedisConnectionInput = z.infer<typeof CreateRedisConnectionSchema> & {
+  app: AppConnection.Redis;
+};
+
+export type TValidateRedisConnectionCredentialsSchema = typeof ValidateRedisConnectionCredentialsSchema;
+
+export type TRedisConnectionConfig = DiscriminativePick<TRedisConnectionInput, "method" | "app" | "credentials"> & {
+  orgId: string;
+};

backend/src/services/auth/auth-login-service.ts

@@ -684,7 +684,8 @@ export const authLoginServiceFactory = ({
     mfaJwtToken,
     ip,
     userAgent,
-    orgId
+    orgId,
+    isRecoveryCode = false
   }: TVerifyMfaTokenDTO) => {
     const appCfg = getConfig();
     const user = await userDAL.findById(userId);
@@ -698,16 +699,21 @@ export const authLoginServiceFactory = ({
           code: mfaToken
         });
       } else if (mfaMethod === MfaMethod.TOTP) {
-        if (mfaToken.length === 6) {
-          await totpService.verifyUserTotp({
-            userId,
-            totp: mfaToken
-          });
-        } else {
+        if (isRecoveryCode) {
           await totpService.verifyWithUserRecoveryCode({
             userId,
             recoveryCode: mfaToken
           });
+        } else {
+          if (mfaToken.length !== 6) {
+            throw new BadRequestError({
+              message: "Please use a valid TOTP code."
+            });
+          }
+          await totpService.verifyUserTotp({
+            userId,
+            totp: mfaToken
+          });
         }
       }
     } catch (err) {

backend/src/services/auth/auth-login-type.ts

@@ -24,6 +24,7 @@ export type TVerifyMfaTokenDTO = {
   ip: string;
   userAgent: string;
   orgId?: string;
+  isRecoveryCode?: boolean;
 };
 
 export type TOauthLoginDTO = {

backend/src/services/auth/auth-password-service.ts

@@ -6,6 +6,7 @@ import { OrgServiceActor } from "@app/lib/types";
 
 import { TAuthTokenServiceFactory } from "../auth-token/auth-token-service";
 import { TokenType } from "../auth-token/auth-token-types";
+import { TOrgMembershipDALFactory } from "../org-membership/org-membership-dal";
 import { SmtpTemplates, TSmtpService } from "../smtp/smtp-service";
 import { TTotpConfigDALFactory } from "../totp/totp-config-dal";
 import { TUserDALFactory } from "../user/user-dal";
@@ -22,6 +23,7 @@ import { ActorType, AuthMethod, AuthTokenType } from "./auth-type";
 type TAuthPasswordServiceFactoryDep = {
   authDAL: TAuthDALFactory;
   userDAL: TUserDALFactory;
+  orgMembershipDAL: Pick<TOrgMembershipDALFactory, "find">;
   tokenService: TAuthTokenServiceFactory;
   smtpService: TSmtpService;
   totpConfigDAL: Pick<TTotpConfigDALFactory, "delete">;
@@ -31,6 +33,7 @@ export type TAuthPasswordFactory = ReturnType<typeof authPaswordServiceFactory>;
 export const authPaswordServiceFactory = ({
   authDAL,
   userDAL,
+  orgMembershipDAL,
   tokenService,
   smtpService,
   totpConfigDAL
@@ -47,21 +50,46 @@ export const authPaswordServiceFactory = ({
 
       if (user && user.isAccepted) {
         const cfg = getConfig();
-        const token = await tokenService.createTokenForUser({
-          type: TokenType.TOKEN_EMAIL_PASSWORD_RESET,
-          userId: user.id
-        });
 
-        await smtpService.sendMail({
-          template: SmtpTemplates.ResetPassword,
-          recipients: [email],
-          subjectLine: "Infisical password reset",
-          substitutions: {
+        const hasEmailAuth = user.authMethods?.includes(AuthMethod.EMAIL);
+
+        if (!hasEmailAuth) {
+          const orgMemberships = await orgMembershipDAL.find({ userId: user.id });
+          const lastLoginMethod =
+            orgMemberships
+              .filter((membership) => membership.lastLoginAuthMethod)
+              .sort((a, b) => (b.updatedAt || new Date(0)).getTime() - (a.updatedAt || new Date(0)).getTime())[0]
+              ?.lastLoginAuthMethod || null;
+          const substitutions = {
             email,
-            token,
-            callback_url: cfg.SITE_URL ? `${cfg.SITE_URL}/password-reset` : ""
-          }
-        });
+            lastLoginMethod,
+            isCloud: cfg.isCloud,
+            siteUrl: cfg.SITE_URL || ""
+          };
+
+          await smtpService.sendMail({
+            template: SmtpTemplates.OAuthPasswordReset,
+            recipients: [email],
+            subjectLine: "Password reset not available",
+            substitutions
+          });
+        } else {
+          const token = await tokenService.createTokenForUser({
+            type: TokenType.TOKEN_EMAIL_PASSWORD_RESET,
+            userId: user.id
+          });
+
+          await smtpService.sendMail({
+            template: SmtpTemplates.ResetPassword,
+            recipients: [email],
+            subjectLine: "Infisical password reset",
+            substitutions: {
+              email,
+              token,
+              callback_url: cfg.SITE_URL ? `${cfg.SITE_URL}/password-reset` : ""
+            }
+          });
+        }
       }
     };
 

backend/src/services/certificate-authority/acme/acme-certificate-authority-fns.ts

@@ -23,6 +23,9 @@ import {
 } from "@app/services/certificate/certificate-types";
 import { TKmsServiceFactory } from "@app/services/kms/kms-service";
 import { TPkiSubscriberDALFactory } from "@app/services/pki-subscriber/pki-subscriber-dal";
+import { TPkiSyncDALFactory } from "@app/services/pki-sync/pki-sync-dal";
+import { TPkiSyncQueueFactory } from "@app/services/pki-sync/pki-sync-queue";
+import { triggerAutoSyncForSubscriber } from "@app/services/pki-sync/pki-sync-utils";
 import { TProjectDALFactory } from "@app/services/project/project-dal";
 import { getProjectKmsCertificateKeyId } from "@app/services/project/project-fns";
 
@@ -56,6 +59,8 @@ type TAcmeCertificateAuthorityFnsDeps = {
     "encryptWithKmsKey" | "generateKmsKey" | "createCipherPairWithDataKey" | "decryptWithKmsKey"
   >;
   pkiSubscriberDAL: Pick<TPkiSubscriberDALFactory, "findById">;
+  pkiSyncDAL: Pick<TPkiSyncDALFactory, "find">;
+  pkiSyncQueue: Pick<TPkiSyncQueueFactory, "queuePkiSyncSyncCertificatesById">;
   projectDAL: Pick<TProjectDALFactory, "findById" | "findOne" | "updateById" | "transaction">;
 };
 
@@ -109,7 +114,9 @@ export const AcmeCertificateAuthorityFns = ({
   certificateSecretDAL,
   kmsService,
   projectDAL,
-  pkiSubscriberDAL
+  pkiSubscriberDAL,
+  pkiSyncDAL,
+  pkiSyncQueue
 }: TAcmeCertificateAuthorityFnsDeps) => {
   const createCertificateAuthority = async ({
     name,
@@ -524,6 +531,8 @@ export const AcmeCertificateAuthorityFns = ({
         tx
       );
     });
+
+    await triggerAutoSyncForSubscriber(subscriber.id, { pkiSyncDAL, pkiSyncQueue });
   };
 
   return {

backend/src/services/certificate-authority/azure-ad-cs/azure-ad-cs-certificate-authority-fns.ts

@@ -26,6 +26,9 @@ import {
 import { TKmsServiceFactory } from "@app/services/kms/kms-service";
 import { TPkiSubscriberDALFactory } from "@app/services/pki-subscriber/pki-subscriber-dal";
 import { TPkiSubscriberProperties } from "@app/services/pki-subscriber/pki-subscriber-types";
+import { TPkiSyncDALFactory } from "@app/services/pki-sync/pki-sync-dal";
+import { TPkiSyncQueueFactory } from "@app/services/pki-sync/pki-sync-queue";
+import { triggerAutoSyncForSubscriber } from "@app/services/pki-sync/pki-sync-utils";
 import { TProjectDALFactory } from "@app/services/project/project-dal";
 import { getProjectKmsCertificateKeyId } from "@app/services/project/project-fns";
 
@@ -55,6 +58,8 @@ type TAzureAdCsCertificateAuthorityFnsDeps = {
     "encryptWithKmsKey" | "generateKmsKey" | "createCipherPairWithDataKey" | "decryptWithKmsKey"
   >;
   pkiSubscriberDAL: Pick<TPkiSubscriberDALFactory, "findById">;
+  pkiSyncDAL: Pick<TPkiSyncDALFactory, "find">;
+  pkiSyncQueue: Pick<TPkiSyncQueueFactory, "queuePkiSyncSyncCertificatesById">;
   projectDAL: Pick<TProjectDALFactory, "findById" | "findOne" | "updateById" | "transaction">;
 };
 
@@ -584,7 +589,9 @@ export const AzureAdCsCertificateAuthorityFns = ({
   certificateSecretDAL,
   kmsService,
   projectDAL,
-  pkiSubscriberDAL
+  pkiSubscriberDAL,
+  pkiSyncDAL,
+  pkiSyncQueue
 }: TAzureAdCsCertificateAuthorityFnsDeps) => {
   const createCertificateAuthority = async ({
     name,
@@ -1024,6 +1031,8 @@ export const AzureAdCsCertificateAuthorityFns = ({
       );
     });
 
+    await triggerAutoSyncForSubscriber(subscriber.id, { pkiSyncDAL, pkiSyncQueue });
+
     return {
       certificate: certificatePem,
       certificateChain: certificateChainPem,

backend/src/services/certificate-authority/certificate-authority-queue.ts

@@ -20,6 +20,8 @@ import { TCertificateBodyDALFactory } from "../certificate/certificate-body-dal"
 import { TCertificateSecretDALFactory } from "../certificate/certificate-secret-dal";
 import { TPkiSubscriberDALFactory } from "../pki-subscriber/pki-subscriber-dal";
 import { SubscriberOperationStatus } from "../pki-subscriber/pki-subscriber-types";
+import { TPkiSyncDALFactory } from "../pki-sync/pki-sync-dal";
+import { TPkiSyncQueueFactory } from "../pki-sync/pki-sync-queue";
 import { AcmeCertificateAuthorityFns } from "./acme/acme-certificate-authority-fns";
 import { AzureAdCsCertificateAuthorityFns } from "./azure-ad-cs/azure-ad-cs-certificate-authority-fns";
 import { TCertificateAuthorityDALFactory } from "./certificate-authority-dal";
@@ -50,6 +52,8 @@ type TCertificateAuthorityQueueFactoryDep = {
   certificateSecretDAL: Pick<TCertificateSecretDALFactory, "create">;
   queueService: TQueueServiceFactory;
   pkiSubscriberDAL: Pick<TPkiSubscriberDALFactory, "findById" | "updateById">;
+  pkiSyncDAL: Pick<TPkiSyncDALFactory, "find">;
+  pkiSyncQueue: Pick<TPkiSyncQueueFactory, "queuePkiSyncSyncCertificatesById">;
 };
 
 export type TCertificateAuthorityQueueFactory = ReturnType<typeof certificateAuthorityQueueFactory>;
@@ -68,7 +72,9 @@ export const certificateAuthorityQueueFactory = ({
   externalCertificateAuthorityDAL,
   certificateBodyDAL,
   certificateSecretDAL,
-  pkiSubscriberDAL
+  pkiSubscriberDAL,
+  pkiSyncDAL,
+  pkiSyncQueue
 }: TCertificateAuthorityQueueFactoryDep) => {
   const acmeFns = AcmeCertificateAuthorityFns({
     appConnectionDAL,
@@ -80,7 +86,9 @@ export const certificateAuthorityQueueFactory = ({
     certificateSecretDAL,
     kmsService,
     pkiSubscriberDAL,
-    projectDAL
+    projectDAL,
+    pkiSyncDAL,
+    pkiSyncQueue
   });
 
   const azureAdCsFns = AzureAdCsCertificateAuthorityFns({
@@ -93,7 +101,9 @@ export const certificateAuthorityQueueFactory = ({
     certificateSecretDAL,
     kmsService,
     pkiSubscriberDAL,
-    projectDAL
+    projectDAL,
+    pkiSyncDAL,
+    pkiSyncQueue
   });
 
   // TODO 1: auto-periodic rotation

backend/src/services/certificate-authority/certificate-authority-service.ts

@@ -13,6 +13,8 @@ import { TCertificateDALFactory } from "../certificate/certificate-dal";
 import { TCertificateSecretDALFactory } from "../certificate/certificate-secret-dal";
 import { TKmsServiceFactory } from "../kms/kms-service";
 import { TPkiSubscriberDALFactory } from "../pki-subscriber/pki-subscriber-dal";
+import { TPkiSyncDALFactory } from "../pki-sync/pki-sync-dal";
+import { TPkiSyncQueueFactory } from "../pki-sync/pki-sync-queue";
 import { TProjectDALFactory } from "../project/project-dal";
 import {
   AcmeCertificateAuthorityFns,
@@ -68,6 +70,8 @@ type TCertificateAuthorityServiceFactoryDep = {
     "encryptWithKmsKey" | "generateKmsKey" | "createCipherPairWithDataKey" | "decryptWithKmsKey"
   >;
   pkiSubscriberDAL: Pick<TPkiSubscriberDALFactory, "findById">;
+  pkiSyncDAL: Pick<TPkiSyncDALFactory, "find">;
+  pkiSyncQueue: Pick<TPkiSyncQueueFactory, "queuePkiSyncSyncCertificatesById">;
 };
 
 export type TCertificateAuthorityServiceFactory = ReturnType<typeof certificateAuthorityServiceFactory>;
@@ -84,7 +88,9 @@ export const certificateAuthorityServiceFactory = ({
   certificateBodyDAL,
   certificateSecretDAL,
   kmsService,
-  pkiSubscriberDAL
+  pkiSubscriberDAL,
+  pkiSyncDAL,
+  pkiSyncQueue
 }: TCertificateAuthorityServiceFactoryDep) => {
   const acmeFns = AcmeCertificateAuthorityFns({
     appConnectionDAL,
@@ -96,7 +102,9 @@ export const certificateAuthorityServiceFactory = ({
     certificateSecretDAL,
     kmsService,
     pkiSubscriberDAL,
-    projectDAL
+    projectDAL,
+    pkiSyncDAL,
+    pkiSyncQueue
   });
 
   const azureAdCsFns = AzureAdCsCertificateAuthorityFns({
@@ -109,7 +117,9 @@ export const certificateAuthorityServiceFactory = ({
     certificateSecretDAL,
     kmsService,
     pkiSubscriberDAL,
-    projectDAL
+    projectDAL,
+    pkiSyncDAL,
+    pkiSyncQueue
   });
 
   const createCertificateAuthority = async (

backend/src/services/certificate-authority/internal/internal-certificate-authority-fns.ts

@@ -19,6 +19,9 @@ import {
   TAltNameMapping
 } from "@app/services/certificate/certificate-types";
 import { TKmsServiceFactory } from "@app/services/kms/kms-service";
+import { TPkiSyncDALFactory } from "@app/services/pki-sync/pki-sync-dal";
+import { TPkiSyncQueueFactory } from "@app/services/pki-sync/pki-sync-queue";
+import { triggerAutoSyncForSubscriber } from "@app/services/pki-sync/pki-sync-utils";
 import { TProjectDALFactory } from "@app/services/project/project-dal";
 import { getProjectKmsCertificateKeyId } from "@app/services/project/project-fns";
 
@@ -51,6 +54,8 @@ type TInternalCertificateAuthorityFnsDeps = {
   certificateDAL: Pick<TCertificateDALFactory, "create" | "transaction">;
   certificateBodyDAL: Pick<TCertificateBodyDALFactory, "create">;
   certificateSecretDAL: Pick<TCertificateSecretDALFactory, "create">;
+  pkiSyncDAL: Pick<TPkiSyncDALFactory, "find">;
+  pkiSyncQueue: Pick<TPkiSyncQueueFactory, "queuePkiSyncSyncCertificatesById">;
 };
 
 export const InternalCertificateAuthorityFns = ({
@@ -62,7 +67,9 @@ export const InternalCertificateAuthorityFns = ({
   certificateAuthorityCrlDAL,
   certificateDAL,
   certificateBodyDAL,
-  certificateSecretDAL
+  certificateSecretDAL,
+  pkiSyncDAL,
+  pkiSyncQueue
 }: TInternalCertificateAuthorityFnsDeps) => {
   const issueCertificate = async (
     subscriber: TPkiSubscribers,
@@ -251,6 +258,8 @@ export const InternalCertificateAuthorityFns = ({
       );
     });
 
+    await triggerAutoSyncForSubscriber(subscriber.id, { pkiSyncDAL, pkiSyncQueue });
+
     return {
       certificate: leafCert.toString("pem"),
       certificateChain: certificateChainPem,

backend/src/services/certificate/certificate-dal.ts

@@ -1,5 +1,5 @@
 import { TDbClient } from "@app/db";
-import { TableName } from "@app/db/schemas";
+import { TableName, TCertificates } from "@app/db/schemas";
 import { DatabaseError } from "@app/lib/errors";
 import { ormify } from "@app/lib/knex";
 
@@ -25,6 +25,20 @@ export const certificateDALFactory = (db: TDbClient) => {
     }
   };
 
+  const findAllActiveCertsForSubscriber = async ({ subscriberId }: { subscriberId: string }) => {
+    try {
+      const certs = await db
+        .replicaNode()(TableName.Certificate)
+        .where({ pkiSubscriberId: subscriberId, status: CertStatus.ACTIVE })
+        .where("notAfter", ">", new Date())
+        .orderBy("notBefore", "desc");
+
+      return certs;
+    } catch (error) {
+      throw new DatabaseError({ error, name: "Find all active certificates for subscriber" });
+    }
+  };
+
   const countCertificatesInProject = async ({
     projectId,
     friendlyName,
@@ -79,10 +93,33 @@ export const certificateDALFactory = (db: TDbClient) => {
     }
   };
 
+  const findExpiredSyncedCertificates = async (): Promise<TCertificates[]> => {
+    try {
+      const yesterday = new Date();
+      yesterday.setDate(yesterday.getDate() - 1);
+      yesterday.setHours(0, 0, 0, 0);
+
+      const today = new Date();
+      today.setHours(0, 0, 0, 0);
+
+      const certs = await db
+        .replicaNode()(TableName.Certificate)
+        .where("notAfter", ">=", yesterday)
+        .where("notAfter", "<", today)
+        .whereNotNull("pkiSubscriberId");
+
+      return certs;
+    } catch (error) {
+      throw new DatabaseError({ error, name: "Find expired synced certificates" });
+    }
+  };
+
   return {
     ...certificateOrm,
     countCertificatesInProject,
     countCertificatesForPkiSubscriber,
-    findLatestActiveCertForSubscriber
+    findLatestActiveCertForSubscriber,
+    findAllActiveCertsForSubscriber,
+    findExpiredSyncedCertificates
   };
 };

backend/src/services/certificate/certificate-service.ts

@@ -1,3 +1,4 @@
+/* eslint-disable no-await-in-loop */
 import { ForbiddenError } from "@casl/ability";
 import * as x509 from "@peculiar/x509";
 
@@ -20,6 +21,9 @@ import { TCertificateAuthoritySecretDALFactory } from "@app/services/certificate
 import { TKmsServiceFactory } from "@app/services/kms/kms-service";
 import { TPkiCollectionDALFactory } from "@app/services/pki-collection/pki-collection-dal";
 import { TPkiCollectionItemDALFactory } from "@app/services/pki-collection/pki-collection-item-dal";
+import { TPkiSyncDALFactory } from "@app/services/pki-sync/pki-sync-dal";
+import { TPkiSyncQueueFactory } from "@app/services/pki-sync/pki-sync-queue";
+import { triggerAutoSyncForSubscriber } from "@app/services/pki-sync/pki-sync-utils";
 import { TProjectDALFactory } from "@app/services/project/project-dal";
 import { getProjectKmsCertificateKeyId } from "@app/services/project/project-fns";
 
@@ -53,6 +57,8 @@ type TCertificateServiceFactoryDep = {
   projectDAL: Pick<TProjectDALFactory, "findProjectBySlug" | "findOne" | "updateById" | "findById" | "transaction">;
   kmsService: Pick<TKmsServiceFactory, "generateKmsKey" | "encryptWithKmsKey" | "decryptWithKmsKey">;
   permissionService: Pick<TPermissionServiceFactory, "getProjectPermission">;
+  pkiSyncDAL: Pick<TPkiSyncDALFactory, "find">;
+  pkiSyncQueue: Pick<TPkiSyncQueueFactory, "queuePkiSyncSyncCertificatesById">;
 };
 
 export type TCertificateServiceFactory = ReturnType<typeof certificateServiceFactory>;
@@ -69,7 +75,9 @@ export const certificateServiceFactory = ({
   pkiCollectionItemDAL,
   projectDAL,
   kmsService,
-  permissionService
+  permissionService,
+  pkiSyncDAL,
+  pkiSyncQueue
 }: TCertificateServiceFactoryDep) => {
   /**
    * Return details for certificate with serial number [serialNumber]
@@ -158,6 +166,11 @@ export const certificateServiceFactory = ({
 
     const deletedCert = await certificateDAL.deleteById(cert.id);
 
+    // Trigger auto sync for PKI syncs connected to this certificate's subscriber
+    if (cert.pkiSubscriberId) {
+      await triggerAutoSyncForSubscriber(cert.pkiSubscriberId, { pkiSyncDAL, pkiSyncQueue });
+    }
+
     return {
       deletedCert
     };
@@ -222,6 +235,11 @@ export const certificateServiceFactory = ({
       }
     );
 
+    // Trigger auto sync for PKI syncs connected to this certificate's subscriber
+    if (cert.pkiSubscriberId) {
+      await triggerAutoSyncForSubscriber(cert.pkiSubscriberId, { pkiSyncDAL, pkiSyncQueue });
+    }
+
     // Note: External CA revocation handling would go here for supported CA types
     // Currently, only internal CAs and ACME CAs support revocation
 

backend/src/services/connection-queue/connection-queue-fns.ts

@@ -0,0 +1,129 @@
+/* eslint-disable no-await-in-loop */
+import { AxiosError } from "axios";
+
+import { logger } from "@app/lib/logger";
+
+export type RateLimitConfig = {
+  MAX_CONCURRENT_REQUESTS: number;
+  BASE_DELAY: number;
+  MAX_DELAY: number;
+  MAX_RETRIES: number;
+  RATE_LIMIT_STATUS_CODES: number[];
+};
+
+export type RateLimitContext = {
+  operation: string;
+  identifier?: string;
+  syncId: string;
+};
+
+export type ConcurrencyContext = {
+  operation: string;
+  syncId: string;
+};
+
+export const sleep = (ms: number): Promise<void> =>
+  new Promise((resolve) => {
+    setTimeout(resolve, ms);
+  });
+
+export const createRateLimitErrorChecker =
+  (config: RateLimitConfig) =>
+  (error: unknown): boolean => {
+    if (error instanceof AxiosError) {
+      return (
+        config.RATE_LIMIT_STATUS_CODES.includes(error.response?.status || 0) ||
+        error.message.toLowerCase().includes("rate limit") ||
+        error.message.toLowerCase().includes("throttl")
+      );
+    }
+    return false;
+  };
+
+export const createRateLimitRetry =
+  (config: RateLimitConfig, isRateLimitError: (error: unknown) => boolean) =>
+  async <T>(fn: () => Promise<T>, context: RateLimitContext, retryCount = 0): Promise<T> => {
+    try {
+      return await fn();
+    } catch (error) {
+      if (isRateLimitError(error) && retryCount < config.MAX_RETRIES) {
+        const delay = Math.min(config.BASE_DELAY * 2 ** retryCount, config.MAX_DELAY);
+
+        logger.warn(
+          {
+            syncId: context.syncId,
+            operation: context.operation,
+            identifier: context.identifier,
+            retryCount: retryCount + 1,
+            delayMs: delay,
+            error: error instanceof AxiosError ? error.message : String(error)
+          },
+          "Rate limit hit, retrying with exponential backoff"
+        );
+
+        await sleep(delay);
+        return createRateLimitRetry(config, isRateLimitError)(fn, context, retryCount + 1);
+      }
+
+      throw error;
+    }
+  };
+
+export const createConcurrencyLimitExecutor =
+  (
+    config: RateLimitConfig,
+    withRateLimitRetry: <T>(fn: () => Promise<T>, context: RateLimitContext, retryCount?: number) => Promise<T>
+  ) =>
+  async <T, R>(
+    items: T[],
+    executor: (item: T) => Promise<R>,
+    context: ConcurrencyContext,
+    concurrencyLimit = config.MAX_CONCURRENT_REQUESTS
+  ): Promise<PromiseSettledResult<R>[]> => {
+    const results: PromiseSettledResult<R>[] = [];
+
+    for (let i = 0; i < items.length; i += concurrencyLimit) {
+      const batch = items.slice(i, i + concurrencyLimit);
+
+      logger.debug(
+        {
+          syncId: context.syncId,
+          operation: context.operation,
+          batchStart: i + 1,
+          batchEnd: Math.min(i + concurrencyLimit, items.length),
+          totalItems: items.length
+        },
+        "Processing batch with rate limit protection"
+      );
+
+      const batchPromises = batch.map((item, batchIndex) =>
+        withRateLimitRetry(() => executor(item), {
+          operation: context.operation,
+          identifier: `batch-${i + batchIndex + 1}`,
+          syncId: context.syncId
+        })
+      );
+
+      const batchResults = await Promise.allSettled(batchPromises);
+      results.push(...batchResults);
+
+      if (i + concurrencyLimit < items.length) {
+        await sleep(100);
+      }
+    }
+
+    return results;
+  };
+
+export const createConnectionQueue = (config: RateLimitConfig) => {
+  const isRateLimitError = createRateLimitErrorChecker(config);
+  const withRateLimitRetry = createRateLimitRetry(config, isRateLimitError);
+  const executeWithConcurrencyLimit = createConcurrencyLimitExecutor(config, withRateLimitRetry);
+
+  return {
+    sleep,
+    isRateLimitError,
+    withRateLimitRetry,
+    executeWithConcurrencyLimit
+  };
+};

backend/src/services/connection-queue/index.ts

@@ -0,0 +1 @@
+export * from "./connection-queue-fns";

backend/src/services/group-project/group-project-service.ts

@@ -37,13 +37,16 @@ type TGroupProjectServiceFactoryDep = {
     TGroupProjectMembershipRoleDALFactory,
     "create" | "transaction" | "insertMany" | "delete"
   >;
-  userGroupMembershipDAL: Pick<TUserGroupMembershipDALFactory, "findGroupMembersNotInProject">;
+  userGroupMembershipDAL: Pick<TUserGroupMembershipDALFactory, "findGroupMembersNotInProject" | "find">;
   projectDAL: Pick<TProjectDALFactory, "findOne" | "findProjectGhostUser" | "findById">;
   projectKeyDAL: Pick<TProjectKeyDALFactory, "findLatestProjectKey" | "delete" | "insertMany" | "transaction">;
   projectRoleDAL: Pick<TProjectRoleDALFactory, "find">;
   projectBotDAL: TProjectBotDALFactory;
   groupDAL: Pick<TGroupDALFactory, "findOne" | "findAllGroupPossibleMembers">;
-  permissionService: Pick<TPermissionServiceFactory, "getProjectPermission" | "getProjectPermissionByRole">;
+  permissionService: Pick<
+    TPermissionServiceFactory,
+    "getProjectPermission" | "getProjectPermissionByRole" | "invalidateProjectPermissionCache"
+  >;
 };
 
 export type TGroupProjectServiceFactory = ReturnType<typeof groupProjectServiceFactory>;
@@ -263,6 +266,8 @@ export const groupProjectServiceFactory = ({
       return groupProjectMembership;
     });
 
+    await permissionService.invalidateProjectPermissionCache(projectId);
+
     return projectGroup;
   };
 
@@ -372,6 +377,8 @@ export const groupProjectServiceFactory = ({
       return groupProjectMembershipRoleDAL.insertMany(sanitizedProjectMembershipRoles, tx);
     });
 
+    await permissionService.invalidateProjectPermissionCache(projectId);
+
     return updatedRoles;
   };
 
@@ -404,14 +411,18 @@ export const groupProjectServiceFactory = ({
     ForbiddenError.from(permission).throwUnlessCan(ProjectPermissionGroupActions.Delete, ProjectPermissionSub.Groups);
 
     const deletedProjectGroup = await groupProjectDAL.transaction(async (tx) => {
-      const groupMembers = await userGroupMembershipDAL.findGroupMembersNotInProject(group.id, project.id, tx);
+      const groupMembersNotInProject = await userGroupMembershipDAL.findGroupMembersNotInProject(
+        group.id,
+        project.id,
+        tx
+      );
 
-      if (groupMembers.length) {
+      if (groupMembersNotInProject.length) {
         await projectKeyDAL.delete(
           {
             projectId: project.id,
             $in: {
-              receiverId: groupMembers.map(({ user: { id } }) => id)
+              receiverId: groupMembersNotInProject.map(({ user: { id } }) => id)
             }
           },
           tx
@@ -422,6 +433,8 @@ export const groupProjectServiceFactory = ({
       return projectGroup;
     });
 
+    await permissionService.invalidateProjectPermissionCache(projectId);
+
     return deletedProjectGroup;
   };
 

backend/src/services/identity-project/identity-project-service.ts

@@ -35,7 +35,10 @@ type TIdentityProjectServiceFactoryDep = {
   projectDAL: Pick<TProjectDALFactory, "findById">;
   projectRoleDAL: Pick<TProjectRoleDALFactory, "find">;
   identityOrgMembershipDAL: Pick<TIdentityOrgDALFactory, "findOne">;
-  permissionService: Pick<TPermissionServiceFactory, "getProjectPermission" | "getProjectPermissionByRole">;
+  permissionService: Pick<
+    TPermissionServiceFactory,
+    "getProjectPermission" | "getProjectPermissionByRole" | "invalidateProjectPermissionCache"
+  >;
 };
 
 export type TIdentityProjectServiceFactory = ReturnType<typeof identityProjectServiceFactory>;
@@ -165,6 +168,9 @@ export const identityProjectServiceFactory = ({
       const identityRoles = await identityProjectMembershipRoleDAL.insertMany(sanitizedProjectMembershipRoles, tx);
       return { ...identityProjectMembership, roles: identityRoles };
     });
+
+    await permissionService.invalidateProjectPermissionCache(projectId);
+
     return projectIdentity;
   };
 
@@ -272,6 +278,8 @@ export const identityProjectServiceFactory = ({
       return identityProjectMembershipRoleDAL.insertMany(sanitizedProjectMembershipRoles, tx);
     });
 
+    await permissionService.invalidateProjectPermissionCache(projectId);
+
     return updatedRoles;
   };
 
@@ -302,6 +310,9 @@ export const identityProjectServiceFactory = ({
     );
 
     const [deletedIdentity] = await identityProjectDAL.delete({ identityId, projectId });
+
+    await permissionService.invalidateProjectPermissionCache(projectId);
+
     return deletedIdentity;
   };
 

backend/src/services/pki-subscriber/pki-subscriber-service.ts

@@ -1,3 +1,4 @@
+/* eslint-disable no-await-in-loop */
 /* eslint-disable no-bitwise */
 import { ForbiddenError, subject } from "@casl/ability";
 import * as x509 from "@peculiar/x509";
@@ -36,6 +37,9 @@ import {
 import { TCertificateAuthoritySecretDALFactory } from "@app/services/certificate-authority/certificate-authority-secret-dal";
 import { TKmsServiceFactory } from "@app/services/kms/kms-service";
 import { TPkiSubscriberDALFactory } from "@app/services/pki-subscriber/pki-subscriber-dal";
+import { TPkiSyncDALFactory } from "@app/services/pki-sync/pki-sync-dal";
+import { TPkiSyncQueueFactory } from "@app/services/pki-sync/pki-sync-queue";
+import { triggerAutoSyncForSubscriber } from "@app/services/pki-sync/pki-sync-utils";
 import { TProjectDALFactory } from "@app/services/project/project-dal";
 import { getProjectKmsCertificateKeyId } from "@app/services/project/project-fns";
 
@@ -79,6 +83,8 @@ type TPkiSubscriberServiceFactoryDep = {
   kmsService: Pick<TKmsServiceFactory, "generateKmsKey" | "decryptWithKmsKey" | "encryptWithKmsKey">;
   permissionService: Pick<TPermissionServiceFactory, "getProjectPermission">;
   internalCaFns: ReturnType<typeof InternalCertificateAuthorityFns>;
+  pkiSyncDAL: Pick<TPkiSyncDALFactory, "find">;
+  pkiSyncQueue: Pick<TPkiSyncQueueFactory, "queuePkiSyncSyncCertificatesById">;
 };
 
 export type TPkiSubscriberServiceFactory = ReturnType<typeof pkiSubscriberServiceFactory>;
@@ -96,7 +102,9 @@ export const pkiSubscriberServiceFactory = ({
   kmsService,
   permissionService,
   certificateAuthorityQueue,
-  internalCaFns
+  internalCaFns,
+  pkiSyncDAL,
+  pkiSyncQueue
 }: TPkiSubscriberServiceFactoryDep) => {
   const createSubscriber = async ({
     name,
@@ -413,7 +421,12 @@ export const pkiSubscriberServiceFactory = ({
 
     const ca = await certificateAuthorityDAL.findByIdWithAssociatedCa(subscriber.caId);
     if (ca.internalCa?.id) {
-      return internalCaFns.issueCertificate(subscriber, ca);
+      const result = await internalCaFns.issueCertificate(subscriber, ca);
+
+      // Trigger auto sync for PKI syncs connected to this subscriber after certificate issuance
+      await triggerAutoSyncForSubscriber(subscriber.id, { pkiSyncDAL, pkiSyncQueue });
+
+      return result;
     }
 
     throw new BadRequestError({ message: "CA does not support immediate issuance of certificates" });
@@ -671,6 +684,9 @@ export const pkiSubscriberServiceFactory = ({
       return cert;
     });
 
+    // Trigger auto sync for PKI syncs connected to this subscriber after certificate signing
+    await triggerAutoSyncForSubscriber(subscriber.id, { pkiSyncDAL, pkiSyncQueue });
+
     return {
       certificate: leafCert.toString("pem"),
       certificateChain: `${issuingCaCertificate}\n${caCertChain}`.trim(),

backend/src/services/pki-sync/azure-key-vault/azure-key-vault-pki-sync-constants.ts

@@ -0,0 +1,52 @@
+import RE2 from "re2";
+
+import { AppConnection } from "@app/services/app-connection/app-connection-enums";
+import { PkiSync } from "@app/services/pki-sync/pki-sync-enums";
+
+/**
+ * Azure Key Vault naming constraints for certificates
+ */
+export const AZURE_KEY_VAULT_CERTIFICATE_NAMING = {
+  /**
+   * Regular expression pattern for valid Azure Key Vault certificate names
+   * Must contain only alphanumeric characters and hyphens (a-z, A-Z, 0-9, -)
+   * Must be 1-127 characters long
+   */
+  NAME_PATTERN: new RE2("^[a-zA-Z0-9-]{1,127}$"),
+
+  /**
+   * String of characters that are forbidden in Azure Key Vault certificate names
+   */
+  FORBIDDEN_CHARACTERS: "!@#$%^&*()+=[]{}|\\:;\"'<>,.?/~` _",
+
+  /**
+   * Maximum length for certificate names in Azure Key Vault
+   */
+  MAX_NAME_LENGTH: 127,
+
+  /**
+   * Minimum length for certificate names in Azure Key Vault
+   */
+  MIN_NAME_LENGTH: 1,
+
+  /**
+   * String representation of the allowed character pattern (for UI display)
+   */
+  ALLOWED_CHARACTER_PATTERN: "^[a-zA-Z0-9-]{1,127}$"
+} as const;
+
+/**
+ * Azure Key Vault PKI Sync list option configuration
+ */
+export const AZURE_KEY_VAULT_PKI_SYNC_LIST_OPTION = {
+  name: "Azure Key Vault" as const,
+  connection: AppConnection.AzureKeyVault,
+  destination: PkiSync.AzureKeyVault,
+  canImportCertificates: false,
+  canRemoveCertificates: true,
+  defaultCertificateNameSchema: "Infisical-PKI-Sync-{{certificateId}}",
+  forbiddenCharacters: AZURE_KEY_VAULT_CERTIFICATE_NAMING.FORBIDDEN_CHARACTERS,
+  allowedCharacterPattern: AZURE_KEY_VAULT_CERTIFICATE_NAMING.ALLOWED_CHARACTER_PATTERN,
+  maxCertificateNameLength: AZURE_KEY_VAULT_CERTIFICATE_NAMING.MAX_NAME_LENGTH,
+  minCertificateNameLength: AZURE_KEY_VAULT_CERTIFICATE_NAMING.MIN_NAME_LENGTH
+} as const;

backend/src/services/pki-sync/azure-key-vault/azure-key-vault-pki-sync-fns.ts

@@ -0,0 +1,680 @@
+/* eslint-disable no-await-in-loop */
+import { AxiosError } from "axios";
+import * as crypto from "crypto";
+
+import { request } from "@app/lib/config/request";
+import { logger } from "@app/lib/logger";
+import { TAppConnectionDALFactory } from "@app/services/app-connection/app-connection-dal";
+import { getAzureConnectionAccessToken } from "@app/services/app-connection/azure-key-vault";
+import { createConnectionQueue, RateLimitConfig } from "@app/services/connection-queue";
+import { TKmsServiceFactory } from "@app/services/kms/kms-service";
+import { matchesCertificateNameSchema } from "@app/services/pki-sync/pki-sync-fns";
+import { TCertificateMap } from "@app/services/pki-sync/pki-sync-types";
+
+import { PkiSyncError } from "../pki-sync-errors";
+import { TPkiSyncWithCredentials } from "../pki-sync-types";
+import { GetAzureKeyVaultCertificate, TAzureKeyVaultPkiSyncConfig } from "./azure-key-vault-pki-sync-types";
+
+const AZURE_RATE_LIMIT_CONFIG: RateLimitConfig = {
+  MAX_CONCURRENT_REQUESTS: 10,
+  BASE_DELAY: 1000,
+  MAX_DELAY: 30000,
+  MAX_RETRIES: 3,
+  RATE_LIMIT_STATUS_CODES: [429, 503]
+};
+
+const azureConnectionQueue = createConnectionQueue(AZURE_RATE_LIMIT_CONFIG);
+
+const { withRateLimitRetry, executeWithConcurrencyLimit } = azureConnectionQueue;
+
+const extractCertificateNameFromId = (certificateId: string): string => {
+  return certificateId.substring(certificateId.lastIndexOf("/") + 1);
+};
+
+const isInfisicalManagedCertificate = (certificateName: string, pkiSync: TPkiSyncWithCredentials): boolean => {
+  const syncOptions = pkiSync.syncOptions as { certificateNameSchema?: string } | undefined;
+  const certificateNameSchema = syncOptions?.certificateNameSchema;
+
+  if (certificateNameSchema) {
+    const environment = "global";
+    return matchesCertificateNameSchema(certificateName, environment, certificateNameSchema);
+  }
+
+  return certificateName.startsWith("Infisical-PKI-Sync-");
+};
+
+type TAzureKeyVaultPkiSyncFactoryDeps = {
+  appConnectionDAL: Pick<TAppConnectionDALFactory, "findById" | "updateById">;
+  kmsService: Pick<TKmsServiceFactory, "createCipherPairWithDataKey">;
+};
+
+const parseCertificateX509Props = (certPem: string) => {
+  try {
+    const cert = new crypto.X509Certificate(certPem);
+
+    const { subject } = cert;
+
+    const sans = {
+      dns_names: [] as string[],
+      emails: [] as string[],
+      upns: [] as string[]
+    };
+
+    if (cert.subjectAltName) {
+      const sanEntries = cert.subjectAltName.split(", ");
+      for (const entry of sanEntries) {
+        if (entry.startsWith("DNS:")) {
+          sans.dns_names.push(entry.substring(4));
+        } else if (entry.startsWith("email:")) {
+          sans.emails.push(entry.substring(6));
+        } else if (entry.startsWith("othername:UPN:")) {
+          sans.upns.push(entry.substring(14));
+        }
+      }
+    }
+
+    return {
+      subject,
+      sans
+    };
+  } catch (error) {
+    logger.warn(
+      { error: error instanceof Error ? error.message : String(error) },
+      "Failed to parse certificate X.509 properties, using empty values"
+    );
+    return {
+      subject: "",
+      sans: {
+        dns_names: [],
+        emails: [],
+        upns: []
+      }
+    };
+  }
+};
+
+const parseCertificateKeyProps = (certPem: string) => {
+  try {
+    const publicKeyObject = crypto.createPublicKey(certPem);
+    const keyDetails = publicKeyObject.asymmetricKeyDetails;
+
+    if (!keyDetails) {
+      if (publicKeyObject.asymmetricKeyType === "rsa") {
+        const pubKeyStr = publicKeyObject.export({ type: "spki", format: "der" }).toString("hex");
+        const estimatedBits = pubKeyStr.length * 4;
+
+        let keySize = 2048;
+        if (estimatedBits >= 4000) {
+          keySize = 4096;
+        } else if (estimatedBits >= 3000) {
+          keySize = 3072;
+        } else if (estimatedBits >= 2000) {
+          keySize = 2048;
+        } else if (estimatedBits >= 1000) {
+          keySize = 1024;
+        }
+
+        return {
+          kty: "RSA",
+          key_size: keySize
+        };
+      }
+
+      if (publicKeyObject.asymmetricKeyType === "ec") {
+        return {
+          kty: "EC",
+          curve: "P-256"
+        };
+      }
+
+      return {
+        kty: "RSA",
+        key_size: 2048
+      };
+    }
+
+    if (publicKeyObject.asymmetricKeyType === "rsa") {
+      const modulusLength = keyDetails.modulusLength || 2048;
+      return {
+        kty: "RSA",
+        key_size: modulusLength
+      };
+    }
+
+    if (publicKeyObject.asymmetricKeyType === "ec") {
+      const { namedCurve } = keyDetails;
+      let curveName = "P-256";
+
+      switch (namedCurve) {
+        case "prime256v1":
+        case "secp256r1":
+          curveName = "P-256";
+          break;
+        case "secp384r1":
+          curveName = "P-384";
+          break;
+        case "secp521r1":
+          curveName = "P-521";
+          break;
+        default:
+          curveName = "P-256";
+      }
+
+      return {
+        kty: "EC",
+        curve: curveName
+      };
+    }
+
+    const keyType = publicKeyObject.asymmetricKeyType;
+    if (keyType && !["rsa", "ec"].includes(keyType)) {
+      throw new Error(`Unsupported certificate key type: ${keyType}. Azure Key Vault only supports RSA and EC keys.`);
+    }
+
+    logger.warn({ keyType }, "Unable to determine certificate key type, defaulting to RSA 2048");
+    return {
+      kty: "RSA",
+      key_size: 2048
+    };
+  } catch (error) {
+    logger.warn(
+      { error: error instanceof Error ? error.message : String(error) },
+      "Failed to parse certificate key properties, defaulting to RSA 2048"
+    );
+    return {
+      kty: "RSA",
+      key_size: 2048
+    };
+  }
+};
+
+export const azureKeyVaultPkiSyncFactory = ({ kmsService, appConnectionDAL }: TAzureKeyVaultPkiSyncFactoryDeps) => {
+  const $getAzureKeyVaultCertificates = async (accessToken: string, vaultBaseUrl: string, syncId = "unknown") => {
+    const paginateAzureKeyVaultCertificates = async () => {
+      let result: GetAzureKeyVaultCertificate[] = [];
+
+      let currentUrl = `${vaultBaseUrl}/certificates?api-version=7.4`;
+
+      while (currentUrl) {
+        const urlToFetch = currentUrl; // Capture current URL to avoid loop function issue
+        const res = await withRateLimitRetry(
+          () =>
+            request.get<{ value: GetAzureKeyVaultCertificate[]; nextLink: string }>(urlToFetch, {
+              headers: {
+                Authorization: `Bearer ${accessToken}`
+              }
+            }),
+          { operation: "list-certificates", syncId }
+        );
+
+        result = result.concat(res.data.value);
+        currentUrl = res.data.nextLink;
+      }
+
+      return result;
+    };
+
+    const getAzureKeyVaultCertificates = await paginateAzureKeyVaultCertificates();
+
+    const enabledAzureKeyVaultCertificates = getAzureKeyVaultCertificates.filter((cert) => cert.attributes.enabled);
+
+    // disabled certificates to skip sending updates to
+    const disabledAzureKeyVaultCertificateKeys = getAzureKeyVaultCertificates
+      .filter(({ attributes }) => !attributes.enabled)
+      .map((certificate) => extractCertificateNameFromId(certificate.id));
+
+    // Use rate-limited concurrent execution for fetching certificate details
+    const certificateResults = await executeWithConcurrencyLimit(
+      enabledAzureKeyVaultCertificates,
+      async (getAzureKeyVaultCertificate) => {
+        const azureKeyVaultCertificate = await request.get<GetAzureKeyVaultCertificate>(
+          `${getAzureKeyVaultCertificate.id}?api-version=7.4`,
+          {
+            headers: {
+              Authorization: `Bearer ${accessToken}`
+            }
+          }
+        );
+
+        let certPem = "";
+        if (azureKeyVaultCertificate.data.cer) {
+          try {
+            // Azure Key Vault stores certificate in base64 DER format
+            // We need to convert it to PEM format with proper headers
+            const base64Cert = azureKeyVaultCertificate.data.cer;
+            const base64Lines = base64Cert.match(/.{1,64}/g);
+            if (!base64Lines) {
+              throw new Error("Failed to format base64 certificate data");
+            }
+            certPem = `-----BEGIN CERTIFICATE-----\n${base64Lines.join("\n")}\n-----END CERTIFICATE-----`;
+          } catch (error) {
+            logger.warn(
+              {
+                error: error instanceof Error ? error.message : String(error),
+                certificateId: getAzureKeyVaultCertificate.id
+              },
+              "Failed to convert Azure Key Vault certificate to PEM format, skipping certificate"
+            );
+            certPem = ""; // Skip this certificate if we can't convert it properly
+          }
+        }
+
+        return {
+          ...azureKeyVaultCertificate.data,
+          key: extractCertificateNameFromId(getAzureKeyVaultCertificate.id),
+          cert: certPem,
+          privateKey: "" // Private keys cannot be extracted from Azure Key Vault for security reasons
+        };
+      },
+      { operation: "fetch-certificate-details", syncId }
+    );
+
+    const successfulCertificates = certificateResults
+      .filter(
+        (
+          result
+        ): result is PromiseFulfilledResult<
+          GetAzureKeyVaultCertificate & {
+            key: string;
+            cert: string;
+            privateKey: string;
+          }
+        > => result.status === "fulfilled"
+      )
+      .map((result) => result.value);
+
+    // Log any failures
+    const failedFetches = certificateResults.filter((result) => result.status === "rejected");
+    if (failedFetches.length > 0) {
+      logger.warn(
+        {
+          syncId,
+          failedCount: failedFetches.length,
+          totalCount: enabledAzureKeyVaultCertificates.length
+        },
+        "Some certificate details could not be fetched from Azure Key Vault"
+      );
+    }
+
+    const res: Record<string, { cert: string; privateKey: string }> = successfulCertificates.reduce(
+      (obj, certificate) => ({
+        ...obj,
+        [certificate.key]: {
+          cert: certificate.cert,
+          privateKey: certificate.privateKey
+        }
+      }),
+      {} as Record<string, { cert: string; privateKey: string }>
+    );
+
+    return {
+      vaultCertificates: res,
+      disabledAzureKeyVaultCertificateKeys
+    };
+  };
+
+  const syncCertificates = async (pkiSync: TPkiSyncWithCredentials, certificateMap: TCertificateMap) => {
+    const { accessToken } = await getAzureConnectionAccessToken(pkiSync.connection.id, appConnectionDAL, kmsService);
+
+    // Cast destination config to Azure Key Vault config
+    const destinationConfig = pkiSync.destinationConfig as TAzureKeyVaultPkiSyncConfig;
+
+    const { vaultCertificates, disabledAzureKeyVaultCertificateKeys } = await $getAzureKeyVaultCertificates(
+      accessToken,
+      destinationConfig.vaultBaseUrl,
+      pkiSync.id
+    );
+
+    const setCertificates: {
+      key: string;
+      cert: string;
+      privateKey: string;
+      certificateChain?: string;
+    }[] = [];
+
+    // Track which certificates should exist in Azure Key Vault
+    const activeCertificateNames = Object.keys(certificateMap);
+
+    // Iterate through certificates to sync to Azure Key Vault
+    Object.entries(certificateMap).forEach(([certName, { cert, privateKey, certificateChain }]) => {
+      if (disabledAzureKeyVaultCertificateKeys.includes(certName)) {
+        return;
+      }
+
+      const existingCert = vaultCertificates[certName];
+      const shouldUpdateCert = !existingCert || existingCert.cert !== cert;
+
+      if (shouldUpdateCert) {
+        setCertificates.push({
+          key: certName,
+          cert,
+          privateKey,
+          certificateChain
+        });
+      }
+    });
+
+    // Identify expired/removed certificates that need to be cleaned up from Azure Key Vault
+    // Only remove certificates that were managed by Infisical (match naming schema)
+    const certificatesToRemove = Object.keys(vaultCertificates).filter(
+      (vaultCertName) =>
+        isInfisicalManagedCertificate(vaultCertName, pkiSync) &&
+        !activeCertificateNames.includes(vaultCertName) &&
+        !disabledAzureKeyVaultCertificateKeys.includes(vaultCertName)
+    );
+
+    // Upload certificates to Azure Key Vault with rate limiting
+    const uploadResults = await executeWithConcurrencyLimit(
+      setCertificates,
+      async ({ key, cert, privateKey, certificateChain }) => {
+        try {
+          // Combine private key, certificate, and certificate chain in PEM format for Azure Key Vault
+          let combinedPem = "";
+
+          if (privateKey) {
+            combinedPem = privateKey.trim();
+          }
+
+          if (combinedPem) {
+            combinedPem = `${combinedPem}\n${cert.trim()}`;
+          } else {
+            combinedPem = cert.trim();
+          }
+
+          if (certificateChain) {
+            const trimmedChain = certificateChain.trim();
+            if (trimmedChain) {
+              combinedPem = `${combinedPem}\n${trimmedChain}`;
+            }
+          }
+
+          // Convert to base64 for Azure Key Vault import
+          const base64Cert = Buffer.from(combinedPem).toString("base64");
+
+          // Parse certificate to extract X.509 properties and key properties
+          const x509Props = parseCertificateX509Props(cert);
+          const keyProps = parseCertificateKeyProps(cert);
+
+          // Build key_props based on key type
+          const keyPropsConfig = {
+            exportable: true,
+            reuse_key: false,
+            ...keyProps
+          };
+
+          const importData = {
+            value: base64Cert,
+            policy: {
+              key_props: keyPropsConfig,
+              secret_props: {
+                contentType: "application/x-pem-file"
+              },
+              x509_props: x509Props
+            },
+            attributes: {
+              enabled: true,
+              exportable: true
+            }
+          };
+
+          const response = await request.post(
+            `${destinationConfig.vaultBaseUrl}/certificates/${encodeURIComponent(key)}/import?api-version=7.4`,
+            importData,
+            {
+              headers: {
+                Authorization: `Bearer ${accessToken}`,
+                "Content-Type": "application/json"
+              }
+            }
+          );
+
+          return { key, success: true, response: response.data as unknown };
+        } catch (error) {
+          if (error instanceof AxiosError) {
+            const errorMessage =
+              error.response?.data && typeof error.response.data === "object" && "error" in error.response.data
+                ? (error.response.data as { error?: { message?: string } }).error?.message || error.message
+                : error.message;
+
+            // Check if the error is due to certificate in deleted but recoverable state
+            const isDeletedButRecoverable =
+              errorMessage.includes("deleted but recoverable state") || errorMessage.includes("name cannot be reused");
+
+            if (isDeletedButRecoverable) {
+              logger.warn(
+                { certificateKey: key, syncId: pkiSync.id },
+                "Certificate exists in deleted but recoverable state in Azure Key Vault - skipping upload"
+              );
+              return { key, success: false, skipped: true, reason: "Certificate in deleted but recoverable state" };
+            }
+
+            throw new PkiSyncError({
+              message: `Failed to upload certificate ${key} to Azure Key Vault: ${errorMessage}`,
+              cause: error,
+              context: {
+                certificateKey: key,
+                statusCode: error.response?.status,
+                responseData: error.response?.data
+              }
+            });
+          }
+          throw error;
+        }
+      },
+      { operation: "upload-certificates", syncId: pkiSync.id }
+    );
+
+    const results = uploadResults;
+    const failedUploads = results.filter((result) => result.status === "rejected");
+    const fulfilledResults = results.filter((result) => result.status === "fulfilled");
+
+    // Separate successful uploads from skipped certificates
+    const successfulUploads = fulfilledResults.filter(
+      (result) => result.status === "fulfilled" && result.value.success
+    );
+    const skippedUploads = fulfilledResults.filter((result) => result.status === "fulfilled" && result.value.skipped);
+
+    // Remove expired/removed certificates from Azure Key Vault
+    let removedCertificates = 0;
+    let failedRemovals = 0;
+
+    if (certificatesToRemove.length > 0) {
+      const removeResults = await executeWithConcurrencyLimit(
+        certificatesToRemove,
+        async (certName) => {
+          try {
+            await request.delete(
+              `${destinationConfig.vaultBaseUrl}/certificates/${encodeURIComponent(certName)}?api-version=7.4`,
+              {
+                headers: {
+                  Authorization: `Bearer ${accessToken}`
+                }
+              }
+            );
+
+            return { key: certName, success: true };
+          } catch (error) {
+            // If certificate doesn't exist (404), consider it as successfully removed
+            if (error instanceof AxiosError && error.response?.status === 404) {
+              return { key: certName, success: true, alreadyRemoved: true };
+            }
+
+            logger.error(
+              { error, syncId: pkiSync.id, certificateName: certName },
+              "Failed to remove expired/removed certificate from Azure Key Vault"
+            );
+
+            // Don't throw here - we want to continue with other operations
+            return { key: certName, success: false, error: error as Error };
+          }
+        },
+        { operation: "remove-certificates", syncId: pkiSync.id }
+      );
+      const successfulRemovals = removeResults.filter(
+        (result) => result.status === "fulfilled" && result.value.success
+      );
+      removedCertificates = successfulRemovals.length;
+      failedRemovals = removeResults.length - removedCertificates;
+
+      if (failedRemovals > 0) {
+        logger.warn(
+          {
+            syncId: pkiSync.id,
+            failedRemovals,
+            successfulRemovals: removedCertificates
+          },
+          "Some expired/removed certificates could not be removed from Azure Key Vault"
+        );
+      }
+    }
+
+    // Collect detailed information for UI feedback
+    const details: {
+      failedUploads?: Array<{ name: string; error: string }>;
+      failedRemovals?: Array<{ name: string; error: string }>;
+      skippedCertificates?: Array<{ name: string; reason: string }>;
+    } = {};
+
+    // Collect skipped certificate details
+    if (skippedUploads.length > 0) {
+      details.skippedCertificates = skippedUploads.map((result) => {
+        const certificateName = result.status === "fulfilled" ? result.value.key : "unknown";
+        return {
+          name: certificateName,
+          reason: "Azure Key Vault constraints or certificate already up to date"
+        };
+      });
+    }
+
+    // Collect failed upload details
+    if (failedUploads.length > 0) {
+      details.failedUploads = failedUploads.map((failure, index) => {
+        const certificateName = setCertificates[index]?.key || "unknown";
+        let errorMessage = "Unknown error";
+
+        if (failure.status === "rejected") {
+          errorMessage = (failure.reason as Error)?.message || "Unknown error";
+        }
+
+        return {
+          name: certificateName,
+          error: errorMessage
+        };
+      });
+
+      logger.error(
+        {
+          syncId: pkiSync.id,
+          failedUploads: details.failedUploads,
+          failedCount: failedUploads.length
+        },
+        "Some certificates failed to upload to Azure Key Vault"
+      );
+    }
+
+    // Collect failed removal details
+    if (failedRemovals > 0) {
+      const failedRemovalNames = certificatesToRemove.slice(-failedRemovals);
+      details.failedRemovals = failedRemovalNames.map((certName) => ({
+        name: certName,
+        error: "Failed to remove from Azure Key Vault"
+      }));
+
+      logger.warn(
+        {
+          syncId: pkiSync.id,
+          failedRemovals: details.failedRemovals,
+          successfulRemovals: removedCertificates
+        },
+        "Some expired/removed certificates could not be removed from Azure Key Vault"
+      );
+    }
+
+    return {
+      uploaded: successfulUploads.length,
+      removed: removedCertificates,
+      failedRemovals,
+      skipped: Object.keys(certificateMap).length - setCertificates.length,
+      details: Object.keys(details).length > 0 ? details : undefined
+    };
+  };
+
+  const removeCertificates = async (pkiSync: TPkiSyncWithCredentials, certificateNames: string[]) => {
+    const { accessToken } = await getAzureConnectionAccessToken(pkiSync.connection.id, appConnectionDAL, kmsService);
+
+    // Cast destination config to Azure Key Vault config
+    const destinationConfig = pkiSync.destinationConfig as TAzureKeyVaultPkiSyncConfig;
+
+    // Only remove certificates that are managed by Infisical (match naming schema)
+    const infisicalManagedCertNames = certificateNames.filter((certName) =>
+      isInfisicalManagedCertificate(certName, pkiSync)
+    );
+
+    const results = await executeWithConcurrencyLimit(
+      infisicalManagedCertNames,
+      async (certName) => {
+        try {
+          const response = await request.delete(
+            `${destinationConfig.vaultBaseUrl}/certificates/${encodeURIComponent(certName)}?api-version=7.4`,
+            {
+              headers: {
+                Authorization: `Bearer ${accessToken}`
+              }
+            }
+          );
+
+          return { key: certName, success: true, response: response.data as unknown };
+        } catch (error) {
+          if (error instanceof AxiosError) {
+            // If certificate doesn't exist (404), consider it as successfully removed
+            if (error.response?.status === 404) {
+              return { key: certName, success: true, alreadyRemoved: true };
+            }
+
+            throw new PkiSyncError({
+              message: `Failed to remove certificate ${certName} from Azure Key Vault`,
+              cause: error,
+              context: {
+                certificateKey: certName,
+                statusCode: error.response?.status,
+                responseData: error.response?.data
+              }
+            });
+          }
+          throw error;
+        }
+      },
+      { operation: "remove-specific-certificates", syncId: pkiSync.id }
+    );
+    const failedRemovals = results.filter((result) => result.status === "rejected");
+
+    if (failedRemovals.length > 0) {
+      const failedReasons = failedRemovals.map((failure) => {
+        if (failure.status === "rejected") {
+          return (failure.reason as Error)?.message || "Unknown error";
+        }
+        return "Unknown error";
+      });
+
+      throw new PkiSyncError({
+        message: `Failed to remove ${failedRemovals.length} certificate(s) from Azure Key Vault`,
+        context: {
+          failedReasons,
+          totalCertificates: infisicalManagedCertNames.length,
+          failedCount: failedRemovals.length
+        }
+      });
+    }
+
+    return {
+      removed: infisicalManagedCertNames.length - failedRemovals.length,
+      failed: failedRemovals.length,
+      skipped: certificateNames.length - infisicalManagedCertNames.length
+    };
+  };
+
+  return {
+    syncCertificates,
+    removeCertificates
+  };
+};

backend/src/services/pki-sync/azure-key-vault/azure-key-vault-pki-sync-schemas.ts

@@ -0,0 +1,74 @@
+import RE2 from "re2";
+import { z } from "zod";
+
+import { AppConnection } from "@app/services/app-connection/app-connection-enums";
+import { PkiSync } from "@app/services/pki-sync/pki-sync-enums";
+import { PkiSyncSchema } from "@app/services/pki-sync/pki-sync-schemas";
+
+import { AZURE_KEY_VAULT_CERTIFICATE_NAMING } from "./azure-key-vault-pki-sync-constants";
+
+export const AzureKeyVaultPkiSyncConfigSchema = z.object({
+  vaultBaseUrl: z.string().url()
+});
+
+const AzureKeyVaultPkiSyncOptionsSchema = z.object({
+  canImportCertificates: z.boolean().default(false),
+  canRemoveCertificates: z.boolean().default(true),
+  certificateNameSchema: z
+    .string()
+    .optional()
+    .refine(
+      (schema) => {
+        if (!schema) return true;
+
+        const testName = schema
+          .replace(new RE2("\\{\\{certificateId\\}\\}", "g"), "")
+          .replace(new RE2("\\{\\{environment\\}\\}", "g"), "");
+
+        const hasForbiddenChars = AZURE_KEY_VAULT_CERTIFICATE_NAMING.FORBIDDEN_CHARACTERS.split("").some((char) =>
+          testName.includes(char)
+        );
+
+        return AZURE_KEY_VAULT_CERTIFICATE_NAMING.NAME_PATTERN.test(testName) && !hasForbiddenChars;
+      },
+      {
+        message:
+          "Certificate name schema must result in names that contain only alphanumeric characters and hyphens (a-z, A-Z, 0-9, -) and be 1-127 characters long when compiled for Azure Key Vault"
+      }
+    )
+});
+
+export const AzureKeyVaultPkiSyncSchema = PkiSyncSchema.extend({
+  destination: z.literal(PkiSync.AzureKeyVault),
+  destinationConfig: AzureKeyVaultPkiSyncConfigSchema,
+  syncOptions: AzureKeyVaultPkiSyncOptionsSchema
+});
+
+export const CreateAzureKeyVaultPkiSyncSchema = z.object({
+  name: z.string().trim().min(1).max(64),
+  description: z.string().optional(),
+  isAutoSyncEnabled: z.boolean().default(true),
+  destinationConfig: AzureKeyVaultPkiSyncConfigSchema,
+  syncOptions: AzureKeyVaultPkiSyncOptionsSchema.optional().default({}),
+  subscriberId: z.string().optional(),
+  connectionId: z.string(),
+  projectId: z.string().trim().min(1)
+});
+
+export const UpdateAzureKeyVaultPkiSyncSchema = z.object({
+  name: z.string().trim().min(1).max(64).optional(),
+  description: z.string().optional(),
+  isAutoSyncEnabled: z.boolean().optional(),
+  destinationConfig: AzureKeyVaultPkiSyncConfigSchema.optional(),
+  syncOptions: AzureKeyVaultPkiSyncOptionsSchema.optional(),
+  subscriberId: z.string().optional(),
+  connectionId: z.string().optional()
+});
+
+export const AzureKeyVaultPkiSyncListItemSchema = z.object({
+  name: z.literal("Azure Key Vault"),
+  connection: z.literal(AppConnection.AzureKeyVault),
+  destination: z.literal(PkiSync.AzureKeyVault),
+  canImportCertificates: z.literal(false),
+  canRemoveCertificates: z.literal(false)
+});

backend/src/services/pki-sync/azure-key-vault/azure-key-vault-pki-sync-types.ts

@@ -0,0 +1,38 @@
+import { z } from "zod";
+
+import { TAzureKeyVaultConnection } from "@app/services/app-connection/azure-key-vault";
+
+import {
+  AzureKeyVaultPkiSyncConfigSchema,
+  AzureKeyVaultPkiSyncSchema,
+  CreateAzureKeyVaultPkiSyncSchema,
+  UpdateAzureKeyVaultPkiSyncSchema
+} from "./azure-key-vault-pki-sync-schemas";
+
+export type GetAzureKeyVaultCertificate = {
+  id: string;
+  value: string;
+  attributes: {
+    enabled: boolean;
+    created: number;
+    updated: number;
+    recoveryLevel: string;
+    tags?: Record<string, string>;
+  };
+  x5t?: string;
+  contentType?: string;
+  key?: string;
+  cer?: string;
+};
+
+export type TAzureKeyVaultPkiSyncConfig = z.infer<typeof AzureKeyVaultPkiSyncConfigSchema>;
+
+export type TAzureKeyVaultPkiSync = z.infer<typeof AzureKeyVaultPkiSyncSchema>;
+
+export type TAzureKeyVaultPkiSyncInput = z.infer<typeof CreateAzureKeyVaultPkiSyncSchema>;
+
+export type TAzureKeyVaultPkiSyncUpdate = z.infer<typeof UpdateAzureKeyVaultPkiSyncSchema>;
+
+export type TAzureKeyVaultPkiSyncWithCredentials = TAzureKeyVaultPkiSync & {
+  connection: TAzureKeyVaultConnection;
+};

backend/src/services/pki-sync/azure-key-vault/index.ts

@@ -0,0 +1,4 @@
+export * from "./azure-key-vault-pki-sync-constants";
+export * from "./azure-key-vault-pki-sync-fns";
+export * from "./azure-key-vault-pki-sync-schemas";
+export * from "./azure-key-vault-pki-sync-types";

backend/src/services/pki-sync/pki-sync-cleanup-queue.ts

@@ -0,0 +1,94 @@
+import { getConfig } from "@app/lib/config/env";
+import { logger } from "@app/lib/logger";
+import { QueueJobs, QueueName, TQueueServiceFactory } from "@app/queue";
+
+import { TPkiSyncDALFactory } from "./pki-sync-dal";
+import { TPkiSyncQueueFactory } from "./pki-sync-queue";
+
+type TPkiSyncCleanupQueueServiceFactoryDep = {
+  queueService: TQueueServiceFactory;
+  pkiSyncDAL: Pick<TPkiSyncDALFactory, "findPkiSyncsWithExpiredCertificates">;
+  pkiSyncQueue: Pick<TPkiSyncQueueFactory, "queuePkiSyncSyncCertificatesById">;
+};
+
+export type TPkiSyncCleanupQueueServiceFactory = ReturnType<typeof pkiSyncCleanupQueueServiceFactory>;
+
+export const pkiSyncCleanupQueueServiceFactory = ({
+  queueService,
+  pkiSyncDAL,
+  pkiSyncQueue
+}: TPkiSyncCleanupQueueServiceFactoryDep) => {
+  const appCfg = getConfig();
+
+  const syncExpiredCertificatesForPkiSyncs = async () => {
+    try {
+      const pkiSyncsWithExpiredCerts = await pkiSyncDAL.findPkiSyncsWithExpiredCertificates();
+
+      if (pkiSyncsWithExpiredCerts.length === 0) {
+        logger.info("No PKI syncs found with certificates that expired the previous day");
+        return;
+      }
+
+      logger.info(
+        `Found ${pkiSyncsWithExpiredCerts.length} PKI sync(s) with certificates that expired the previous day`
+      );
+
+      // Trigger sync for each PKI sync that has expired certificates
+      for (const { id: syncId, subscriberId } of pkiSyncsWithExpiredCerts) {
+        try {
+          // eslint-disable-next-line no-await-in-loop
+          await pkiSyncQueue.queuePkiSyncSyncCertificatesById({
+            syncId
+          });
+          logger.info(
+            `Successfully queued PKI sync ${syncId} for subscriber ${subscriberId} due to expired certificates`
+          );
+        } catch (error) {
+          logger.error(error, `Failed to queue PKI sync ${syncId} for subscriber ${subscriberId}`);
+        }
+      }
+    } catch (error) {
+      logger.error(error, "Failed to sync expired certificates for PKI syncs");
+      throw error;
+    }
+  };
+
+  const init = async () => {
+    if (appCfg.isSecondaryInstance) {
+      return;
+    }
+
+    await queueService.stopRepeatableJob(
+      QueueName.PkiSyncCleanup,
+      QueueJobs.PkiSyncCleanup,
+      { pattern: "0 0 * * *", utc: true },
+      QueueName.PkiSyncCleanup // just a job id
+    );
+
+    await queueService.startPg<QueueName.PkiSyncCleanup>(
+      QueueJobs.PkiSyncCleanup,
+      async () => {
+        try {
+          logger.info(`${QueueName.PkiSyncCleanup}: queue task started`);
+          await syncExpiredCertificatesForPkiSyncs();
+          logger.info(`${QueueName.PkiSyncCleanup}: queue task completed`);
+        } catch (error) {
+          logger.error(error, `${QueueName.PkiSyncCleanup}: PKI sync cleanup failed`);
+          throw error;
+        }
+      },
+      {
+        batchSize: 1,
+        workerCount: 1,
+        pollingIntervalSeconds: 120
+      }
+    );
+
+    await queueService.schedulePg(QueueJobs.PkiSyncCleanup, "0 0 * * *", undefined, { tz: "UTC" });
+  };
+
+  return {
+    init,
+    syncExpiredCertificatesForPkiSyncs
+  };
+};

backend/src/services/pki-sync/pki-sync-dal.ts

@@ -0,0 +1,314 @@
+import { Knex } from "knex";
+
+import { TDbClient } from "@app/db";
+import { TableName, TPkiSyncs } from "@app/db/schemas";
+import { DatabaseError } from "@app/lib/errors";
+import { buildFindFilter, ormify, prependTableNameToFindFilter, selectAllTableCols } from "@app/lib/knex";
+
+import { PkiSync } from "./pki-sync-enums";
+
+export type TPkiSyncDALFactory = ReturnType<typeof pkiSyncDALFactory>;
+
+type PkiSyncFindFilter = Parameters<typeof buildFindFilter<TPkiSyncs>>[0];
+
+const basePkiSyncQuery = ({ filter, db, tx }: { db: TDbClient; filter?: PkiSyncFindFilter; tx?: Knex }) => {
+  const query = (tx || db.replicaNode())(TableName.PkiSync)
+    .leftJoin(TableName.AppConnection, `${TableName.PkiSync}.connectionId`, `${TableName.AppConnection}.id`)
+    .select(selectAllTableCols(TableName.PkiSync))
+    .select(
+      // app connection fields
+      db.ref("name").withSchema(TableName.AppConnection).as("appConnectionName"),
+      db.ref("app").withSchema(TableName.AppConnection).as("appConnectionApp"),
+      db.ref("encryptedCredentials").withSchema(TableName.AppConnection).as("appConnectionEncryptedCredentials"),
+      db.ref("orgId").withSchema(TableName.AppConnection).as("appConnectionOrgId"),
+      db.ref("projectId").withSchema(TableName.AppConnection).as("appConnectionProjectId"),
+      db.ref("method").withSchema(TableName.AppConnection).as("appConnectionMethod"),
+      db.ref("description").withSchema(TableName.AppConnection).as("appConnectionDescription"),
+      db.ref("version").withSchema(TableName.AppConnection).as("appConnectionVersion"),
+      db.ref("gatewayId").withSchema(TableName.AppConnection).as("appConnectionGatewayId"),
+      db.ref("createdAt").withSchema(TableName.AppConnection).as("appConnectionCreatedAt"),
+      db.ref("updatedAt").withSchema(TableName.AppConnection).as("appConnectionUpdatedAt"),
+      db
+        .ref("isPlatformManagedCredentials")
+        .withSchema(TableName.AppConnection)
+        .as("appConnectionIsPlatformManagedCredentials")
+    );
+
+  if (filter) {
+    // eslint-disable-next-line @typescript-eslint/no-misused-promises
+    void query.where(buildFindFilter(prependTableNameToFindFilter(TableName.PkiSync, filter)));
+  }
+
+  return query;
+};
+
+const basePkiSyncWithSubscriberQuery = ({
+  filter,
+  db,
+  tx
+}: {
+  db: TDbClient;
+  filter?: PkiSyncFindFilter;
+  tx?: Knex;
+}) => {
+  const query = (tx || db.replicaNode())(TableName.PkiSync)
+    .leftJoin(TableName.AppConnection, `${TableName.PkiSync}.connectionId`, `${TableName.AppConnection}.id`)
+    .leftJoin(TableName.PkiSubscriber, `${TableName.PkiSync}.subscriberId`, `${TableName.PkiSubscriber}.id`)
+    .select(selectAllTableCols(TableName.PkiSync))
+    .select(
+      // app connection fields
+      db.ref("name").withSchema(TableName.AppConnection).as("appConnectionName"),
+      db.ref("app").withSchema(TableName.AppConnection).as("appConnectionApp"),
+      db.ref("encryptedCredentials").withSchema(TableName.AppConnection).as("appConnectionEncryptedCredentials"),
+      db.ref("orgId").withSchema(TableName.AppConnection).as("appConnectionOrgId"),
+      db.ref("projectId").withSchema(TableName.AppConnection).as("appConnectionProjectId"),
+      db.ref("method").withSchema(TableName.AppConnection).as("appConnectionMethod"),
+      db.ref("description").withSchema(TableName.AppConnection).as("appConnectionDescription"),
+      db.ref("version").withSchema(TableName.AppConnection).as("appConnectionVersion"),
+      db.ref("gatewayId").withSchema(TableName.AppConnection).as("appConnectionGatewayId"),
+      db.ref("createdAt").withSchema(TableName.AppConnection).as("appConnectionCreatedAt"),
+      db.ref("updatedAt").withSchema(TableName.AppConnection).as("appConnectionUpdatedAt"),
+      db
+        .ref("isPlatformManagedCredentials")
+        .withSchema(TableName.AppConnection)
+        .as("appConnectionIsPlatformManagedCredentials"),
+      // pki subscriber fields
+      db.ref("id").withSchema(TableName.PkiSubscriber).as("pkiSubscriberId"),
+      db.ref("name").withSchema(TableName.PkiSubscriber).as("subscriberName")
+    );
+
+  if (filter) {
+    // eslint-disable-next-line @typescript-eslint/no-misused-promises
+    void query.where(buildFindFilter(prependTableNameToFindFilter(TableName.PkiSync, filter)));
+  }
+
+  return query;
+};
+
+const expandPkiSync = (pkiSync: Awaited<ReturnType<typeof basePkiSyncQuery>>[number]) => {
+  const {
+    appConnectionName,
+    appConnectionApp,
+    appConnectionEncryptedCredentials,
+    appConnectionOrgId,
+    appConnectionProjectId,
+    appConnectionMethod,
+    appConnectionDescription,
+    appConnectionVersion,
+    appConnectionGatewayId,
+    appConnectionCreatedAt,
+    appConnectionUpdatedAt,
+    appConnectionIsPlatformManagedCredentials,
+    ...el
+  } = pkiSync;
+
+  return {
+    ...el,
+    destination: el.destination as PkiSync,
+    destinationConfig: el.destinationConfig as Record<string, unknown>,
+    syncOptions: el.syncOptions as Record<string, unknown>,
+    appConnectionName,
+    appConnectionApp,
+    connection: {
+      id: el.connectionId,
+      name: appConnectionName,
+      app: appConnectionApp,
+      encryptedCredentials: appConnectionEncryptedCredentials,
+      orgId: appConnectionOrgId,
+      projectId: appConnectionProjectId,
+      method: appConnectionMethod,
+      description: appConnectionDescription,
+      version: appConnectionVersion,
+      gatewayId: appConnectionGatewayId,
+      createdAt: appConnectionCreatedAt,
+      updatedAt: appConnectionUpdatedAt,
+      isPlatformManagedCredentials: appConnectionIsPlatformManagedCredentials
+    }
+  };
+};
+
+const expandPkiSyncWithSubscriber = (pkiSync: Awaited<ReturnType<typeof basePkiSyncWithSubscriberQuery>>[number]) => {
+  const {
+    appConnectionName,
+    appConnectionApp,
+    appConnectionEncryptedCredentials,
+    appConnectionOrgId,
+    appConnectionProjectId,
+    appConnectionMethod,
+    appConnectionDescription,
+    appConnectionVersion,
+    appConnectionGatewayId,
+    appConnectionCreatedAt,
+    appConnectionUpdatedAt,
+    appConnectionIsPlatformManagedCredentials,
+    pkiSubscriberId,
+    subscriberName,
+    ...el
+  } = pkiSync;
+
+  return {
+    ...el,
+    destination: el.destination as PkiSync,
+    destinationConfig: el.destinationConfig as Record<string, unknown>,
+    syncOptions: el.syncOptions as Record<string, unknown>,
+    appConnectionName,
+    appConnectionApp,
+    connection: {
+      id: el.connectionId,
+      name: appConnectionName,
+      app: appConnectionApp,
+      encryptedCredentials: appConnectionEncryptedCredentials,
+      orgId: appConnectionOrgId,
+      projectId: appConnectionProjectId,
+      method: appConnectionMethod,
+      description: appConnectionDescription,
+      version: appConnectionVersion,
+      gatewayId: appConnectionGatewayId,
+      createdAt: appConnectionCreatedAt,
+      updatedAt: appConnectionUpdatedAt,
+      isPlatformManagedCredentials: appConnectionIsPlatformManagedCredentials
+    },
+    subscriber: pkiSubscriberId && subscriberName ? { id: pkiSubscriberId, name: subscriberName } : null
+  };
+};
+
+export const pkiSyncDALFactory = (db: TDbClient) => {
+  const pkiSyncOrm = ormify(db, TableName.PkiSync);
+
+  const findByProjectId = async (projectId: string, tx?: Knex) => {
+    try {
+      const pkiSyncs = await basePkiSyncQuery({ filter: { projectId }, db, tx });
+      return pkiSyncs.map(expandPkiSync);
+    } catch (error) {
+      throw new DatabaseError({ error, name: "Find By Project ID - PKI Sync" });
+    }
+  };
+
+  const findByProjectIdWithSubscribers = async (projectId: string, tx?: Knex) => {
+    try {
+      const pkiSyncs = await basePkiSyncWithSubscriberQuery({ filter: { projectId }, db, tx });
+      return pkiSyncs.map(expandPkiSyncWithSubscriber);
+    } catch (error) {
+      throw new DatabaseError({ error, name: "Find By Project ID With Subscribers - PKI Sync" });
+    }
+  };
+
+  const findBySubscriberId = async (subscriberId: string, tx?: Knex) => {
+    try {
+      const pkiSyncs = await basePkiSyncQuery({ filter: { subscriberId }, db, tx });
+      return pkiSyncs.map(expandPkiSync);
+    } catch (error) {
+      throw new DatabaseError({ error, name: "Find By Subscriber ID - PKI Sync" });
+    }
+  };
+
+  const findByIdAndProjectId = async (id: string, projectId: string, tx?: Knex) => {
+    try {
+      const pkiSync = await basePkiSyncQuery({ filter: { id, projectId }, db, tx }).first();
+      return pkiSync ? expandPkiSync(pkiSync) : undefined;
+    } catch (error) {
+      throw new DatabaseError({ error, name: "Find By ID and Project ID - PKI Sync" });
+    }
+  };
+
+  const findByNameAndProjectId = async (name: string, projectId: string, tx?: Knex) => {
+    try {
+      const pkiSync = await basePkiSyncQuery({ filter: { name, projectId }, db, tx }).first();
+      return pkiSync ? expandPkiSync(pkiSync) : undefined;
+    } catch (error) {
+      throw new DatabaseError({ error, name: "Find By Name and Project ID - PKI Sync" });
+    }
+  };
+
+  const findById = async (id: string, tx?: Knex) => {
+    try {
+      const pkiSync = await basePkiSyncQuery({ filter: { id }, db, tx }).first();
+      return pkiSync ? expandPkiSync(pkiSync) : undefined;
+    } catch (error) {
+      throw new DatabaseError({ error, name: "Find By ID - PKI Sync" });
+    }
+  };
+
+  const findOne = async (filter: Parameters<(typeof pkiSyncOrm)["findOne"]>[0], tx?: Knex) => {
+    try {
+      const pkiSync = await basePkiSyncQuery({ filter, db, tx }).first();
+      return pkiSync ? expandPkiSync(pkiSync) : undefined;
+    } catch (error) {
+      throw new DatabaseError({ error, name: "Find One - PKI Sync" });
+    }
+  };
+
+  const find = async (filter: Parameters<(typeof pkiSyncOrm)["find"]>[0], tx?: Knex) => {
+    try {
+      const pkiSyncs = await basePkiSyncQuery({ filter, db, tx });
+      return pkiSyncs.map(expandPkiSync);
+    } catch (error) {
+      throw new DatabaseError({ error, name: "Find - PKI Sync" });
+    }
+  };
+
+  const create = async (data: Parameters<(typeof pkiSyncOrm)["create"]>[0]) => {
+    const pkiSync = (await pkiSyncOrm.transaction(async (tx) => {
+      const sync = await pkiSyncOrm.create(data, tx);
+      return basePkiSyncQuery({ filter: { id: sync.id }, db, tx }).first();
+    }))!;
+
+    return expandPkiSync(pkiSync);
+  };
+
+  const updateById = async (syncId: string, data: Parameters<(typeof pkiSyncOrm)["updateById"]>[1]) => {
+    const pkiSync = (await pkiSyncOrm.transaction(async (tx) => {
+      const sync = await pkiSyncOrm.updateById(syncId, data, tx);
+      return basePkiSyncQuery({ filter: { id: sync.id }, db, tx }).first();
+    }))!;
+
+    return expandPkiSync(pkiSync);
+  };
+
+  const findPkiSyncsWithExpiredCertificates = async (): Promise<Array<{ id: string; subscriberId: string }>> => {
+    try {
+      const yesterday = new Date();
+      yesterday.setDate(yesterday.getDate() - 1);
+      yesterday.setHours(0, 0, 0, 0);
+
+      const today = new Date();
+      today.setHours(0, 0, 0, 0);
+
+      const pkiSyncs = (await db
+        .replicaNode()(TableName.PkiSync)
+        .select(`${TableName.PkiSync}.id`, `${TableName.PkiSync}.subscriberId`)
+        .innerJoin(
+          TableName.Certificate,
+          `${TableName.PkiSync}.subscriberId`,
+          `${TableName.Certificate}.pkiSubscriberId`
+        )
+        .where(`${TableName.Certificate}.notAfter`, ">=", yesterday)
+        .where(`${TableName.Certificate}.notAfter`, "<", today)
+        .whereNotNull(`${TableName.Certificate}.pkiSubscriberId`)
+        .whereNotNull(`${TableName.PkiSync}.subscriberId`)
+        .groupBy(`${TableName.PkiSync}.id`, `${TableName.PkiSync}.subscriberId`)) as Array<{
+        id: string;
+        subscriberId: string;
+      }>;
+
+      return pkiSyncs;
+    } catch (error) {
+      throw new DatabaseError({ error, name: "Find PKI syncs with expired certificates" });
+    }
+  };
+
+  return {
+    ...pkiSyncOrm,
+    findByProjectId,
+    findByProjectIdWithSubscribers,
+    findBySubscriberId,
+    findByIdAndProjectId,
+    findByNameAndProjectId,
+    findById,
+    findOne,
+    find,
+    create,
+    updateById,
+    findPkiSyncsWithExpiredCertificates
+  };
+};

backend/src/services/pki-sync/pki-sync-enums.ts

@@ -0,0 +1,16 @@
+export enum PkiSync {
+  AzureKeyVault = "azure-key-vault"
+}
+
+export enum PkiSyncStatus {
+  Pending = "pending",
+  Running = "running",
+  Succeeded = "succeeded",
+  Failed = "failed"
+}
+
+export enum PkiSyncAction {
+  SyncCertificates = "sync-certificates",
+  ImportCertificates = "import-certificates",
+  RemoveCertificates = "remove-certificates"
+}

backend/src/services/pki-sync/pki-sync-errors.ts

@@ -0,0 +1,25 @@
+export class PkiSyncError extends Error {
+  public context?: Record<string, unknown>;
+
+  public cause?: Error;
+
+  public shouldRetry: boolean;
+
+  constructor({
+    message,
+    cause,
+    context,
+    shouldRetry = true
+  }: {
+    message: string;
+    cause?: Error;
+    context?: Record<string, unknown>;
+    shouldRetry?: boolean;
+  }) {
+    super(message);
+    this.name = "PkiSyncError";
+    this.cause = cause;
+    this.context = context;
+    this.shouldRetry = shouldRetry;
+  }
+}

backend/src/services/pki-sync/pki-sync-fns.ts

@@ -0,0 +1,223 @@
+import * as handlebars from "handlebars";
+import { z, ZodSchema } from "zod";
+
+import { TLicenseServiceFactory } from "@app/ee/services/license/license-service";
+import { BadRequestError } from "@app/lib/errors";
+import { TAppConnectionDALFactory } from "@app/services/app-connection/app-connection-dal";
+import { TKmsServiceFactory } from "@app/services/kms/kms-service";
+
+import { AZURE_KEY_VAULT_PKI_SYNC_LIST_OPTION } from "./azure-key-vault/azure-key-vault-pki-sync-constants";
+import { azureKeyVaultPkiSyncFactory } from "./azure-key-vault/azure-key-vault-pki-sync-fns";
+import { PkiSync } from "./pki-sync-enums";
+import { TCertificateMap, TPkiSyncWithCredentials } from "./pki-sync-types";
+
+const ENTERPRISE_PKI_SYNCS: PkiSync[] = [];
+
+const PKI_SYNC_LIST_OPTIONS = {
+  [PkiSync.AzureKeyVault]: AZURE_KEY_VAULT_PKI_SYNC_LIST_OPTION
+};
+
+export const enterprisePkiSyncCheck = async (
+  licenseService: Pick<TLicenseServiceFactory, "getPlan">,
+  orgId: string,
+  pkiSyncDestination: PkiSync,
+  errorMessage?: string
+) => {
+  const plan = await licenseService.getPlan(orgId);
+
+  if (!plan.enterpriseCertificateSyncs && ENTERPRISE_PKI_SYNCS.includes(pkiSyncDestination)) {
+    throw new BadRequestError({
+      message: errorMessage || "Failed to create PKI sync due to plan restriction. Upgrade plan to create PKI sync."
+    });
+  }
+};
+
+export const listPkiSyncOptions = () => {
+  return Object.values(PKI_SYNC_LIST_OPTIONS).sort((a, b) => a.name.localeCompare(b.name));
+};
+
+export const getPkiSyncProviderCapabilities = (destination: PkiSync) => {
+  const providerOption = PKI_SYNC_LIST_OPTIONS[destination];
+  if (!providerOption) {
+    throw new BadRequestError({ message: `Unsupported PKI sync destination: ${destination}` });
+  }
+
+  return {
+    canImportCertificates: providerOption.canImportCertificates,
+    canRemoveCertificates: providerOption.canRemoveCertificates
+  };
+};
+
+export const matchesSchema = <T extends ZodSchema>(schema: T, data: unknown): data is z.infer<T> => {
+  return schema.safeParse(data).success;
+};
+
+export const parsePkiSyncErrorMessage = (error: unknown): string => {
+  if (error instanceof Error) {
+    return error.message;
+  }
+
+  if (typeof error === "string") {
+    return error;
+  }
+
+  return "An unknown error occurred during PKI sync operation";
+};
+
+export const applyCertificateNameSchema = (
+  certificateMap: TCertificateMap,
+  environment: string,
+  schema?: string
+): TCertificateMap => {
+  if (!schema) return certificateMap;
+
+  const processedCertificateMap: TCertificateMap = {};
+
+  for (const [certificateId, value] of Object.entries(certificateMap)) {
+    const newName = handlebars.compile(schema)({
+      certificateId,
+      environment
+    });
+
+    processedCertificateMap[newName] = value;
+  }
+
+  return processedCertificateMap;
+};
+
+export const stripCertificateNameSchema = (
+  certificateMap: TCertificateMap,
+  environment: string,
+  schema?: string
+): TCertificateMap => {
+  if (!schema) return certificateMap;
+
+  const compiledSchemaPattern = handlebars.compile(schema)({
+    certificateId: "{{certificateId}}",
+    environment
+  });
+
+  const parts = compiledSchemaPattern.split("{{certificateId}}");
+  const prefix = parts[0];
+  const suffix = parts[parts.length - 1];
+
+  const strippedMap: TCertificateMap = {};
+
+  for (const [name, value] of Object.entries(certificateMap)) {
+    if (!name.startsWith(prefix) || !name.endsWith(suffix)) {
+      // eslint-disable-next-line no-continue
+      continue;
+    }
+
+    const strippedName = name.slice(prefix.length, name.length - suffix.length);
+    strippedMap[strippedName] = value;
+  }
+
+  return strippedMap;
+};
+
+export const matchesCertificateNameSchema = (name: string, environment: string, schema?: string): boolean => {
+  if (!schema) return true;
+
+  const compiledSchemaPattern = handlebars.compile(schema)({
+    certificateId: "{{certificateId}}",
+    environment
+  });
+
+  if (!compiledSchemaPattern.includes("{{certificateId}}")) {
+    return name === compiledSchemaPattern;
+  }
+
+  const parts = compiledSchemaPattern.split("{{certificateId}}");
+  const prefix = parts[0];
+  const suffix = parts[parts.length - 1];
+
+  if (prefix === "" && suffix === "") return true;
+
+  // If prefix is empty, name must end with suffix
+  if (prefix === "") return name.endsWith(suffix);
+
+  // If suffix is empty, name must start with prefix
+  if (suffix === "") return name.startsWith(prefix);
+
+  // Name must start with prefix and end with suffix
+  return name.startsWith(prefix) && name.endsWith(suffix);
+};
+
+const isAzureKeyVaultPkiSync = (pkiSync: TPkiSyncWithCredentials): boolean => {
+  return pkiSync.destination === PkiSync.AzureKeyVault;
+};
+
+export const PkiSyncFns = {
+  getCertificates: async (
+    pkiSync: TPkiSyncWithCredentials,
+    // eslint-disable-next-line @typescript-eslint/no-unused-vars
+    dependencies: {
+      appConnectionDAL: Pick<TAppConnectionDALFactory, "findById" | "updateById">;
+      kmsService: Pick<TKmsServiceFactory, "createCipherPairWithDataKey">;
+    }
+  ): Promise<TCertificateMap> => {
+    switch (pkiSync.destination) {
+      case PkiSync.AzureKeyVault: {
+        throw new Error(
+          "Azure Key Vault does not support importing certificates into Infisical (private keys cannot be extracted)"
+        );
+      }
+      default:
+        throw new Error(`Unsupported PKI sync destination: ${String(pkiSync.destination)}`);
+    }
+  },
+
+  syncCertificates: async (
+    pkiSync: TPkiSyncWithCredentials,
+    certificateMap: TCertificateMap,
+    dependencies: {
+      appConnectionDAL: Pick<TAppConnectionDALFactory, "findById" | "updateById">;
+      kmsService: Pick<TKmsServiceFactory, "createCipherPairWithDataKey">;
+    }
+  ): Promise<{
+    uploaded: number;
+    removed?: number;
+    failedRemovals?: number;
+    skipped: number;
+    details?: {
+      failedUploads?: Array<{ name: string; error: string }>;
+      failedRemovals?: Array<{ name: string; error: string }>;
+      skippedCertificates?: Array<{ name: string; reason: string }>;
+    };
+  }> => {
+    switch (pkiSync.destination) {
+      case PkiSync.AzureKeyVault: {
+        if (!isAzureKeyVaultPkiSync(pkiSync)) {
+          throw new Error("Invalid Azure Key Vault PKI sync configuration");
+        }
+        const azureKeyVaultPkiSync = azureKeyVaultPkiSyncFactory(dependencies);
+        return azureKeyVaultPkiSync.syncCertificates(pkiSync, certificateMap);
+      }
+      default:
+        throw new Error(`Unsupported PKI sync destination: ${String(pkiSync.destination)}`);
+    }
+  },
+
+  removeCertificates: async (
+    pkiSync: TPkiSyncWithCredentials,
+    certificateNames: string[],
+    dependencies: {
+      appConnectionDAL: Pick<TAppConnectionDALFactory, "findById" | "updateById">;
+      kmsService: Pick<TKmsServiceFactory, "createCipherPairWithDataKey">;
+    }
+  ): Promise<void> => {
+    switch (pkiSync.destination) {
+      case PkiSync.AzureKeyVault: {
+        if (!isAzureKeyVaultPkiSync(pkiSync)) {
+          throw new Error("Invalid Azure Key Vault PKI sync configuration");
+        }
+        const azureKeyVaultPkiSync = azureKeyVaultPkiSyncFactory(dependencies);
+        await azureKeyVaultPkiSync.removeCertificates(pkiSync, certificateNames);
+        break;
+      }
+      default:
+        throw new Error(`Unsupported PKI sync destination: ${String(pkiSync.destination)}`);
+    }
+  }
+};

backend/src/services/pki-sync/pki-sync-maps.ts

@@ -0,0 +1,11 @@
+import { AppConnection } from "@app/services/app-connection/app-connection-enums";
+
+import { PkiSync } from "./pki-sync-enums";
+
+export const PKI_SYNC_NAME_MAP: Record<PkiSync, string> = {
+  [PkiSync.AzureKeyVault]: "Azure Key Vault"
+};
+
+export const PKI_SYNC_CONNECTION_MAP: Record<PkiSync, AppConnection> = {
+  [PkiSync.AzureKeyVault]: AppConnection.AzureKeyVault
+};

backend/src/services/pki-sync/pki-sync-queue.ts

@@ -0,0 +1,753 @@
+/* eslint-disable no-await-in-loop */
+import opentelemetry from "@opentelemetry/api";
+import * as x509 from "@peculiar/x509";
+import { AxiosError } from "axios";
+import { Job } from "bullmq";
+import handlebars from "handlebars";
+
+import { EventType, TAuditLogServiceFactory } from "@app/ee/services/audit-log/audit-log-types";
+import { TLicenseServiceFactory } from "@app/ee/services/license/license-service";
+import { KeyStorePrefixes, TKeyStoreFactory } from "@app/keystore/keystore";
+import { getConfig } from "@app/lib/config/env";
+import { logger } from "@app/lib/logger";
+import { QueueJobs, QueueName, TQueueServiceFactory } from "@app/queue";
+import { decryptAppConnectionCredentials } from "@app/services/app-connection/app-connection-fns";
+import { ActorType } from "@app/services/auth/auth-type";
+import { TKmsServiceFactory } from "@app/services/kms/kms-service";
+import { TProjectDALFactory } from "@app/services/project/project-dal";
+import { getProjectKmsCertificateKeyId } from "@app/services/project/project-fns";
+
+import { TAppConnectionDALFactory } from "../app-connection/app-connection-dal";
+import { TCertificateBodyDALFactory } from "../certificate/certificate-body-dal";
+import { TCertificateDALFactory } from "../certificate/certificate-dal";
+import { getCertificateCredentials } from "../certificate/certificate-fns";
+import { TCertificateSecretDALFactory } from "../certificate/certificate-secret-dal";
+import { TCertificateAuthorityCertDALFactory } from "../certificate-authority/certificate-authority-cert-dal";
+import { TCertificateAuthorityDALFactory } from "../certificate-authority/certificate-authority-dal";
+import { getCaCertChain } from "../certificate-authority/certificate-authority-fns";
+import { TPkiSyncDALFactory } from "./pki-sync-dal";
+import { PkiSyncStatus } from "./pki-sync-enums";
+import { PkiSyncError } from "./pki-sync-errors";
+import { enterprisePkiSyncCheck, parsePkiSyncErrorMessage, PkiSyncFns } from "./pki-sync-fns";
+import {
+  TCertificateMap,
+  TPkiSyncImportCertificatesDTO,
+  TPkiSyncRaw,
+  TPkiSyncRemoveCertificatesDTO,
+  TPkiSyncSyncCertificatesDTO,
+  TPkiSyncWithCredentials,
+  TQueuePkiSyncImportCertificatesByIdDTO,
+  TQueuePkiSyncRemoveCertificatesByIdDTO,
+  TQueuePkiSyncSyncCertificatesByIdDTO
+} from "./pki-sync-types";
+
+export type TPkiSyncQueueFactory = ReturnType<typeof pkiSyncQueueFactory>;
+
+type TPkiSyncQueueFactoryDep = {
+  queueService: Pick<TQueueServiceFactory, "queue" | "start">;
+  kmsService: Pick<
+    TKmsServiceFactory,
+    "createCipherPairWithDataKey" | "decryptWithKmsKey" | "generateKmsKey" | "encryptWithKmsKey"
+  >;
+  appConnectionDAL: Pick<TAppConnectionDALFactory, "findById" | "update" | "updateById">;
+  keyStore: Pick<TKeyStoreFactory, "acquireLock" | "setItemWithExpiry" | "getItem">;
+  pkiSyncDAL: Pick<TPkiSyncDALFactory, "findById" | "find" | "updateById" | "deleteById" | "update">;
+  auditLogService: Pick<TAuditLogServiceFactory, "createAuditLog">;
+  projectDAL: TProjectDALFactory;
+  licenseService: Pick<TLicenseServiceFactory, "getPlan">;
+  certificateDAL: Pick<
+    TCertificateDALFactory,
+    "findLatestActiveCertForSubscriber" | "findAllActiveCertsForSubscriber" | "create"
+  >;
+  certificateBodyDAL: Pick<TCertificateBodyDALFactory, "findOne" | "create">;
+  certificateSecretDAL: Pick<TCertificateSecretDALFactory, "findOne" | "create">;
+  certificateAuthorityDAL: Pick<TCertificateAuthorityDALFactory, "findById">;
+  certificateAuthorityCertDAL: Pick<TCertificateAuthorityCertDALFactory, "findById">;
+};
+
+type PkiSyncActionJob = Job<
+  TQueuePkiSyncSyncCertificatesByIdDTO | TQueuePkiSyncImportCertificatesByIdDTO | TQueuePkiSyncRemoveCertificatesByIdDTO
+>;
+
+const JITTER_MS = 10 * 1000;
+const REQUEUE_MS = 30 * 1000;
+const REQUEUE_LIMIT = 30;
+const CONNECTION_CONCURRENCY_LIMIT = 3;
+
+const getRequeueDelay = (failureCount?: number) => {
+  const jitter = Math.random() * JITTER_MS;
+  if (!failureCount) return jitter;
+  return REQUEUE_MS + jitter;
+};
+
+export const pkiSyncQueueFactory = ({
+  queueService,
+  kmsService,
+  appConnectionDAL,
+  keyStore,
+  pkiSyncDAL,
+  auditLogService,
+  projectDAL,
+  licenseService,
+  certificateDAL,
+  certificateBodyDAL,
+  certificateSecretDAL,
+  certificateAuthorityDAL,
+  certificateAuthorityCertDAL
+}: TPkiSyncQueueFactoryDep) => {
+  const appCfg = getConfig();
+
+  const integrationMeter = opentelemetry.metrics.getMeter("PkiSyncs");
+  const syncCertificatesErrorHistogram = integrationMeter.createHistogram("pki_sync_sync_certificates_errors", {
+    description: "PKI Sync - sync certificates errors",
+    unit: "1"
+  });
+  const importCertificatesErrorHistogram = integrationMeter.createHistogram("pki_sync_import_certificates_errors", {
+    description: "PKI Sync - import certificates errors",
+    unit: "1"
+  });
+  const removeCertificatesErrorHistogram = integrationMeter.createHistogram("pki_sync_remove_certificates_errors", {
+    description: "PKI Sync - remove certificates errors",
+    unit: "1"
+  });
+
+  const $isConnectionConcurrencyLimitReached = async (connectionId: string) => {
+    const concurrencyCount = await keyStore.getItem(KeyStorePrefixes.AppConnectionConcurrentJobs(connectionId));
+
+    if (!concurrencyCount) return false;
+
+    const count = Number.parseInt(concurrencyCount, 10);
+
+    if (Number.isNaN(count)) return false;
+
+    return count >= CONNECTION_CONCURRENCY_LIMIT;
+  };
+
+  const $incrementConnectionConcurrencyCount = async (connectionId: string) => {
+    const concurrencyCount = await keyStore.getItem(KeyStorePrefixes.AppConnectionConcurrentJobs(connectionId));
+
+    const currentCount = Number.parseInt(concurrencyCount || "0", 10);
+
+    const incrementedCount = Number.isNaN(currentCount) ? 1 : currentCount + 1;
+
+    await keyStore.setItemWithExpiry(
+      KeyStorePrefixes.AppConnectionConcurrentJobs(connectionId),
+      (REQUEUE_MS * REQUEUE_LIMIT) / 1000, // in seconds
+      incrementedCount
+    );
+  };
+
+  const $decrementConnectionConcurrencyCount = async (connectionId: string) => {
+    const concurrencyCount = await keyStore.getItem(KeyStorePrefixes.AppConnectionConcurrentJobs(connectionId));
+
+    const currentCount = Number.parseInt(concurrencyCount || "0", 10);
+
+    const decrementedCount = Math.max(0, Number.isNaN(currentCount) ? 0 : currentCount - 1);
+
+    await keyStore.setItemWithExpiry(
+      KeyStorePrefixes.AppConnectionConcurrentJobs(connectionId),
+      (REQUEUE_MS * REQUEUE_LIMIT) / 1000, // in seconds
+      decrementedCount
+    );
+  };
+
+  const $getInfisicalCertificates = async (
+    pkiSync: TPkiSyncRaw | TPkiSyncWithCredentials
+  ): Promise<TCertificateMap> => {
+    const { projectId, subscriberId } = pkiSync;
+
+    if (!subscriberId) {
+      throw new PkiSyncError({
+        message: "Invalid PKI Sync source configuration: subscriber no longer exists. Please update source subscriber.",
+        shouldRetry: false
+      });
+    }
+
+    const certificateMap: TCertificateMap = {};
+
+    try {
+      // Get all active certificates for the subscriber (not just the latest)
+      const certificates = await certificateDAL.findAllActiveCertsForSubscriber({
+        subscriberId
+      });
+
+      for (const certificate of certificates) {
+        try {
+          // Get the certificate body and decrypt the certificate data
+          const certBody = await certificateBodyDAL.findOne({ certId: certificate.id });
+
+          if (certBody) {
+            const certificateManagerKeyId = await getProjectKmsCertificateKeyId({
+              projectId: certificate.projectId,
+              projectDAL,
+              kmsService
+            });
+
+            const kmsDecryptor = await kmsService.decryptWithKmsKey({
+              kmsId: certificateManagerKeyId
+            });
+
+            const decryptedCert = await kmsDecryptor({
+              cipherTextBlob: certBody.encryptedCertificate
+            });
+
+            const certObj = new x509.X509Certificate(decryptedCert);
+            const certificatePem = certObj.toString("pem");
+
+            // Get private key using getCertificateCredentials - handle cases where private key doesn't exist
+            let certPrivateKey: string | undefined;
+            try {
+              const credentials = await getCertificateCredentials({
+                certId: certificate.id,
+                projectId: certificate.projectId,
+                certificateSecretDAL,
+                projectDAL,
+                kmsService
+              });
+              certPrivateKey = credentials.certPrivateKey;
+            } catch (credError) {
+              logger.warn(
+                { certificateId: certificate.id, subscriberId, error: credError },
+                "Certificate private key not found - certificate may be imported or key was not stored"
+              );
+              // Continue without private key - some providers may only need the certificate
+              certPrivateKey = undefined;
+            }
+
+            let certificateChain: string | undefined;
+            try {
+              if (certBody.encryptedCertificateChain) {
+                const decryptedCertChain = await kmsDecryptor({
+                  cipherTextBlob: certBody.encryptedCertificateChain
+                });
+                certificateChain = decryptedCertChain.toString();
+              } else if (certificate.caCertId) {
+                const { caCert, caCertChain } = await getCaCertChain({
+                  caCertId: certificate.caCertId,
+                  certificateAuthorityDAL,
+                  certificateAuthorityCertDAL,
+                  projectDAL,
+                  kmsService
+                });
+                certificateChain = `${caCert}\n${caCertChain}`.trim();
+              }
+            } catch (chainError) {
+              logger.warn(
+                { certificateId: certificate.id, subscriberId, error: chainError },
+                "Certificate chain not found or could not be decrypted - certificate may be imported or chain was not stored"
+              );
+              // Continue without certificate chain
+              certificateChain = undefined;
+            }
+
+            let certificateName: string;
+            const syncOptions = pkiSync.syncOptions as { certificateNameSchema?: string } | undefined;
+            const certificateNameSchema = syncOptions?.certificateNameSchema;
+
+            if (certificateNameSchema) {
+              const environment = "global";
+              certificateName = handlebars.compile(certificateNameSchema)({
+                certificateId: certificate.id.replace(/-/g, ""),
+                environment
+              });
+            } else {
+              certificateName = `Infisical-${certificate.id.replace(/-/g, "")}`;
+            }
+
+            certificateMap[certificateName] = {
+              cert: certificatePem,
+              privateKey: certPrivateKey || "",
+              certificateChain
+            };
+          } else {
+            logger.warn({ certificateId: certificate.id, subscriberId }, "Certificate body not found for certificate");
+          }
+        } catch (error) {
+          logger.error(
+            { error, subscriberId, certificateId: certificate.id },
+            "Failed to decrypt certificate for PKI sync"
+          );
+          // Continue with other certificates
+        }
+      }
+    } catch (error) {
+      logger.error(
+        error,
+        `Failed to fetch certificate for subscriber [subscriberId=${subscriberId}] [projectId=${projectId}]`
+      );
+      throw new PkiSyncError({
+        message: `Failed to fetch certificate for PKI subscriber: ${error instanceof Error ? error.message : String(error)}`,
+        shouldRetry: true
+      });
+    }
+
+    return certificateMap;
+  };
+
+  const queuePkiSyncSyncCertificatesById = async (payload: TQueuePkiSyncSyncCertificatesByIdDTO) =>
+    queueService.queue(QueueName.PkiSync, QueueJobs.PkiSyncSyncCertificates, payload, {
+      delay: getRequeueDelay(payload.failedToAcquireLockCount), // this is for delaying re-queued jobs if sync is locked
+      attempts: 5,
+      backoff: {
+        type: "exponential",
+        delay: 3000
+      },
+      removeOnComplete: true,
+      removeOnFail: true
+    });
+
+  const queuePkiSyncImportCertificatesById = async (payload: TQueuePkiSyncImportCertificatesByIdDTO) =>
+    queueService.queue(QueueName.PkiSync, QueueJobs.PkiSyncImportCertificates, payload, {
+      attempts: 5,
+      backoff: {
+        type: "exponential",
+        delay: 3000
+      },
+      removeOnComplete: true,
+      removeOnFail: true
+    });
+
+  const queuePkiSyncRemoveCertificatesById = async (payload: TQueuePkiSyncRemoveCertificatesByIdDTO) =>
+    queueService.queue(QueueName.PkiSync, QueueJobs.PkiSyncRemoveCertificates, payload, {
+      attempts: 5,
+      backoff: {
+        type: "exponential",
+        delay: 3000
+      },
+      removeOnComplete: true,
+      removeOnFail: true
+    });
+
+  const $importCertificates = async (): Promise<TCertificateMap> => {
+    throw new Error("Certificate import functionality is not implemented");
+  };
+
+  const $handleSyncCertificatesJob = async (job: TPkiSyncSyncCertificatesDTO, pkiSync: TPkiSyncRaw) => {
+    const {
+      data: { syncId, auditLogInfo }
+    } = job;
+
+    await enterprisePkiSyncCheck(
+      licenseService,
+      pkiSync.connection.orgId,
+      pkiSync.destination,
+      "Failed to sync certificates due to plan restriction. Upgrade plan to access enterprise PKI syncs."
+    );
+
+    await pkiSyncDAL.updateById(syncId, {
+      syncStatus: PkiSyncStatus.Running
+    });
+
+    logger.info(
+      `PkiSync Sync [syncId=${pkiSync.id}] [destination=${pkiSync.destination}] [projectId=${pkiSync.projectId}] [subscriberId=${pkiSync.subscriberId}] [connectionId=${pkiSync.connectionId}]`
+    );
+
+    let isSynced = false;
+    let syncMessage: string | null = null;
+    let isFinalAttempt = job.attemptsStarted === job.opts.attempts;
+
+    try {
+      const {
+        connection: { orgId, encryptedCredentials, projectId: appConnectionProjectId }
+      } = pkiSync;
+
+      const credentials = await decryptAppConnectionCredentials({
+        orgId,
+        encryptedCredentials,
+        kmsService,
+        projectId: appConnectionProjectId
+      });
+
+      const pkiSyncWithCredentials = {
+        ...pkiSync,
+        connection: {
+          ...pkiSync.connection,
+          credentials
+        }
+      } as TPkiSyncWithCredentials;
+
+      const certificateMap = await $getInfisicalCertificates(pkiSync);
+
+      const syncResult = await PkiSyncFns.syncCertificates(pkiSyncWithCredentials, certificateMap, {
+        appConnectionDAL,
+        kmsService
+      });
+
+      logger.info(
+        {
+          syncId: pkiSync.id,
+          uploaded: syncResult.uploaded || 0,
+          removed: syncResult.removed || 0,
+          failedRemovals: syncResult.failedRemovals || 0,
+          skipped: syncResult.skipped || 0
+        },
+        "PKI sync operation completed with certificate cleanup"
+      );
+
+      isSynced = true;
+    } catch (err) {
+      logger.error(
+        err,
+        `PkiSync Sync Error [syncId=${pkiSync.id}] [destination=${pkiSync.destination}] [projectId=${pkiSync.projectId}] [subscriberId=${pkiSync.subscriberId}] [connectionId=${pkiSync.connectionId}]`
+      );
+
+      if (appCfg.OTEL_TELEMETRY_COLLECTION_ENABLED) {
+        syncCertificatesErrorHistogram.record(1, {
+          version: 1,
+          destination: pkiSync.destination,
+          syncId: pkiSync.id,
+          projectId: pkiSync.projectId,
+          type: err instanceof AxiosError ? "AxiosError" : err?.constructor?.name || "UnknownError",
+          status: err instanceof AxiosError ? err.response?.status : undefined,
+          name: err instanceof Error ? err.name : undefined
+        });
+      }
+
+      syncMessage = parsePkiSyncErrorMessage(err);
+
+      if (err instanceof PkiSyncError && !err.shouldRetry) {
+        isFinalAttempt = true;
+      } else {
+        throw err;
+      }
+    } finally {
+      const ranAt = new Date();
+      const syncStatus = isSynced ? PkiSyncStatus.Succeeded : PkiSyncStatus.Failed;
+
+      await auditLogService.createAuditLog({
+        projectId: pkiSync.projectId,
+        ...(auditLogInfo ?? {
+          actor: {
+            type: ActorType.PLATFORM,
+            metadata: {}
+          }
+        }),
+        event: {
+          type: EventType.PKI_SYNC_SYNC_CERTIFICATES,
+          metadata: {
+            syncId: pkiSync.id,
+            syncMessage,
+            jobId: job.id!,
+            jobRanAt: ranAt
+          }
+        }
+      });
+
+      if (isSynced || isFinalAttempt) {
+        await pkiSyncDAL.updateById(pkiSync.id, {
+          syncStatus,
+          lastSyncJobId: job.id,
+          lastSyncMessage: syncMessage,
+          lastSyncedAt: isSynced ? ranAt : undefined
+        });
+      }
+    }
+  };
+
+  const $handleImportCertificatesJob = async (job: TPkiSyncImportCertificatesDTO, pkiSync: TPkiSyncRaw) => {
+    const {
+      data: { syncId, auditLogInfo }
+    } = job;
+
+    await pkiSyncDAL.updateById(syncId, {
+      importStatus: PkiSyncStatus.Running
+    });
+
+    logger.info(
+      `PkiSync Import [syncId=${pkiSync.id}] [destination=${pkiSync.destination}] [projectId=${pkiSync.projectId}] [subscriberId=${pkiSync.subscriberId}] [connectionId=${pkiSync.connectionId}]`
+    );
+
+    let isSuccess = false;
+    let importMessage: string | null = null;
+    let isFinalAttempt = job.attemptsStarted === job.opts.attempts;
+
+    try {
+      await $importCertificates();
+
+      isSuccess = true;
+    } catch (err) {
+      logger.error(
+        err,
+        `PkiSync Import Error [syncId=${pkiSync.id}] [destination=${pkiSync.destination}] [projectId=${pkiSync.projectId}] [subscriberId=${pkiSync.subscriberId}] [connectionId=${pkiSync.connectionId}]`
+      );
+
+      if (appCfg.OTEL_TELEMETRY_COLLECTION_ENABLED) {
+        importCertificatesErrorHistogram.record(1, {
+          version: 1,
+          destination: pkiSync.destination,
+          syncId: pkiSync.id,
+          projectId: pkiSync.projectId,
+          type: err instanceof AxiosError ? "AxiosError" : err?.constructor?.name || "UnknownError",
+          status: err instanceof AxiosError ? err.response?.status : undefined,
+          name: err instanceof Error ? err.name : undefined
+        });
+      }
+
+      importMessage = parsePkiSyncErrorMessage(err);
+
+      if (err instanceof PkiSyncError && !err.shouldRetry) {
+        isFinalAttempt = true;
+      } else {
+        throw err;
+      }
+    } finally {
+      const ranAt = new Date();
+      const importStatus = isSuccess ? PkiSyncStatus.Succeeded : PkiSyncStatus.Failed;
+
+      await auditLogService.createAuditLog({
+        projectId: pkiSync.projectId,
+        ...(auditLogInfo ?? {
+          actor: {
+            type: ActorType.PLATFORM,
+            metadata: {}
+          }
+        }),
+        event: {
+          type: EventType.PKI_SYNC_IMPORT_CERTIFICATES,
+          metadata: {
+            syncId: pkiSync.id,
+            importMessage,
+            jobId: job.id!,
+            jobRanAt: ranAt
+          }
+        }
+      });
+
+      if (isSuccess || isFinalAttempt) {
+        await pkiSyncDAL.updateById(pkiSync.id, {
+          importStatus,
+          lastImportJobId: job.id,
+          lastImportMessage: importMessage,
+          lastImportedAt: isSuccess ? ranAt : undefined
+        });
+      }
+    }
+  };
+
+  const $handleRemoveCertificatesJob = async (job: TPkiSyncRemoveCertificatesDTO, pkiSync: TPkiSyncRaw) => {
+    const {
+      data: { syncId, auditLogInfo, deleteSyncOnComplete }
+    } = job;
+
+    await enterprisePkiSyncCheck(
+      licenseService,
+      pkiSync.connection.orgId,
+      pkiSync.destination,
+      "Failed to remove certificates due to plan restriction. Upgrade plan to access enterprise PKI syncs."
+    );
+
+    await pkiSyncDAL.updateById(syncId, {
+      removeStatus: PkiSyncStatus.Running
+    });
+
+    logger.info(
+      `PkiSync Remove [syncId=${pkiSync.id}] [destination=${pkiSync.destination}] [projectId=${pkiSync.projectId}] [subscriberId=${pkiSync.subscriberId}] [connectionId=${pkiSync.connectionId}]`
+    );
+
+    let isSuccess = false;
+    let removeMessage: string | null = null;
+    let isFinalAttempt = job.attemptsStarted === job.opts.attempts;
+
+    try {
+      const {
+        connection: { orgId, encryptedCredentials, projectId: appConnectionProjectId }
+      } = pkiSync;
+
+      const credentials = await decryptAppConnectionCredentials({
+        orgId,
+        encryptedCredentials,
+        kmsService,
+        projectId: appConnectionProjectId
+      });
+
+      const certificateMap = await $getInfisicalCertificates(pkiSync);
+
+      await PkiSyncFns.removeCertificates(
+        {
+          ...pkiSync,
+          connection: {
+            ...pkiSync.connection,
+            credentials
+          }
+        } as TPkiSyncWithCredentials,
+        Object.keys(certificateMap),
+        {
+          appConnectionDAL,
+          kmsService
+        }
+      );
+
+      isSuccess = true;
+    } catch (err) {
+      logger.error(
+        err,
+        `PkiSync Remove Error [syncId=${pkiSync.id}] [destination=${pkiSync.destination}] [projectId=${pkiSync.projectId}] [subscriberId=${pkiSync.subscriberId}] [connectionId=${pkiSync.connectionId}]`
+      );
+
+      if (appCfg.OTEL_TELEMETRY_COLLECTION_ENABLED) {
+        removeCertificatesErrorHistogram.record(1, {
+          version: 1,
+          destination: pkiSync.destination,
+          syncId: pkiSync.id,
+          projectId: pkiSync.projectId,
+          type: err instanceof AxiosError ? "AxiosError" : err?.constructor?.name || "UnknownError",
+          status: err instanceof AxiosError ? err.response?.status : undefined,
+          name: err instanceof Error ? err.name : undefined
+        });
+      }
+
+      removeMessage = parsePkiSyncErrorMessage(err);
+
+      if (err instanceof PkiSyncError && !err.shouldRetry) {
+        isFinalAttempt = true;
+      } else {
+        throw err;
+      }
+    } finally {
+      const ranAt = new Date();
+      const removeStatus = isSuccess ? PkiSyncStatus.Succeeded : PkiSyncStatus.Failed;
+
+      await auditLogService.createAuditLog({
+        projectId: pkiSync.projectId,
+        ...(auditLogInfo ?? {
+          actor: {
+            type: ActorType.PLATFORM,
+            metadata: {}
+          }
+        }),
+        event: {
+          type: EventType.PKI_SYNC_REMOVE_CERTIFICATES,
+          metadata: {
+            syncId: pkiSync.id,
+            removeMessage,
+            jobId: job.id!,
+            jobRanAt: ranAt
+          }
+        }
+      });
+
+      if (isSuccess || isFinalAttempt) {
+        if (isSuccess && deleteSyncOnComplete) {
+          await pkiSyncDAL.deleteById(pkiSync.id);
+        } else {
+          await pkiSyncDAL.updateById(pkiSync.id, {
+            removeStatus,
+            lastRemoveJobId: job.id,
+            lastRemoveMessage: removeMessage,
+            lastRemovedAt: isSuccess ? ranAt : undefined
+          });
+        }
+      }
+    }
+  };
+
+  const $handleAcquireLockFailure = async (job: PkiSyncActionJob) => {
+    const { syncId } = job.data;
+
+    switch (job.name) {
+      case QueueJobs.PkiSyncSyncCertificates: {
+        const { failedToAcquireLockCount = 0, ...rest } = job.data as TQueuePkiSyncSyncCertificatesByIdDTO;
+
+        if (failedToAcquireLockCount < REQUEUE_LIMIT) {
+          await queuePkiSyncSyncCertificatesById({ ...rest, failedToAcquireLockCount: failedToAcquireLockCount + 1 });
+          return;
+        }
+
+        await pkiSyncDAL.updateById(syncId, {
+          syncStatus: PkiSyncStatus.Failed,
+          lastSyncMessage:
+            "Failed to run job. This typically happens when a sync is already in progress. Please try again.",
+          lastSyncJobId: job.id
+        });
+
+        break;
+      }
+      case QueueJobs.PkiSyncImportCertificates: {
+        await pkiSyncDAL.updateById(syncId, {
+          importStatus: PkiSyncStatus.Failed,
+          lastImportMessage:
+            "Failed to run job. This typically happens when a sync is already in progress. Please try again.",
+          lastImportJobId: job.id
+        });
+
+        break;
+      }
+      case QueueJobs.PkiSyncRemoveCertificates: {
+        await pkiSyncDAL.updateById(syncId, {
+          removeStatus: PkiSyncStatus.Failed,
+          lastRemoveMessage:
+            "Failed to run job. This typically happens when a sync is already in progress. Please try again.",
+          lastRemoveJobId: job.id
+        });
+
+        break;
+      }
+      default:
+        throw new Error(`Unhandled PKI Sync Job ${String(job.name)}`);
+    }
+  };
+
+  queueService.start(QueueName.PkiSync, async (job) => {
+    const { syncId } = job.data;
+
+    const pkiSync = await pkiSyncDAL.findById(syncId);
+
+    if (!pkiSync) throw new Error(`Cannot find PKI sync with ID ${syncId}`);
+
+    const { connectionId } = pkiSync;
+
+    if (job.name === QueueJobs.PkiSyncSyncCertificates) {
+      const isConcurrentLimitReached = await $isConnectionConcurrencyLimitReached(connectionId);
+
+      if (isConcurrentLimitReached) {
+        await $handleAcquireLockFailure(job as PkiSyncActionJob);
+
+        return;
+      }
+    }
+
+    let lock: Awaited<ReturnType<typeof keyStore.acquireLock>>;
+
+    try {
+      lock = await keyStore.acquireLock(
+        [KeyStorePrefixes.PkiSyncLock(syncId)],
+        // PKI syncs can take excessive amounts of time so we need to keep it locked
+        5 * 60 * 1000
+      );
+    } catch (e) {
+      await $handleAcquireLockFailure(job as PkiSyncActionJob);
+
+      return;
+    }
+
+    try {
+      switch (job.name) {
+        case QueueJobs.PkiSyncSyncCertificates: {
+          await $incrementConnectionConcurrencyCount(connectionId);
+          await $handleSyncCertificatesJob(job as TPkiSyncSyncCertificatesDTO, pkiSync);
+          break;
+        }
+        case QueueJobs.PkiSyncImportCertificates:
+          await $handleImportCertificatesJob(job as TPkiSyncImportCertificatesDTO, pkiSync);
+          break;
+        case QueueJobs.PkiSyncRemoveCertificates:
+          await $handleRemoveCertificatesJob(job as TPkiSyncRemoveCertificatesDTO, pkiSync);
+          break;
+        default:
+          throw new Error(`Unhandled PKI Sync Job ${String(job.name)}`);
+      }
+    } finally {
+      if (job.name === QueueJobs.PkiSyncSyncCertificates) {
+        await $decrementConnectionConcurrencyCount(connectionId);
+      }
+
+      await lock.release();
+    }
+  });
+
+  return {
+    queuePkiSyncSyncCertificatesById,
+    queuePkiSyncImportCertificatesById,
+    queuePkiSyncRemoveCertificatesById
+  };
+};

backend/src/services/pki-sync/pki-sync-schemas.ts

@@ -0,0 +1,61 @@
+import RE2 from "re2";
+import { z } from "zod";
+
+import { PkiSync } from "./pki-sync-enums";
+
+// Schema for PKI sync options configuration
+export const PkiSyncOptionsSchema = z.object({
+  canImportCertificates: z.boolean(),
+  canRemoveCertificates: z.boolean().optional(),
+  certificateNameSchema: z
+    .string()
+    .optional()
+    .refine(
+      (val) => {
+        if (!val) return true;
+
+        const allowedPlaceholdersRegexPart = ["{{certificateId}}"]
+          .map((p) => p.replace(new RE2(/[-/\\^$*+?.()|[\]{}]/g), "\\$&")) // Escape regex special characters
+          .join("|");
+
+        const allowedContentRegex = new RE2(`^([a-zA-Z0-9_\\-/]|${allowedPlaceholdersRegexPart})*$`);
+        const contentIsValid = allowedContentRegex.test(val);
+
+        if (val.trim()) {
+          const certificateIdRegex = new RE2(/\{\{certificateId\}\}/);
+          const certificateIdIsPresent = certificateIdRegex.test(val);
+          return contentIsValid && certificateIdIsPresent;
+        }
+
+        return contentIsValid;
+      },
+      {
+        message:
+          "Certificate name schema must include exactly one {{certificateId}} placeholder. Only alphanumeric characters (a-z, A-Z, 0-9), dashes (-), underscores (_), and slashes (/) are allowed besides the placeholders."
+      }
+    )
+});
+
+// Schema for destination-specific configurations
+export const PkiSyncDestinationConfigSchema = z.object({
+  destination: z.nativeEnum(PkiSync),
+  config: z.record(z.unknown())
+});
+
+// Base PKI sync schema for API responses
+export const PkiSyncSchema = z.object({
+  id: z.string().uuid(),
+  name: z.string().max(255),
+  description: z.string().nullable().optional(),
+  destination: z.nativeEnum(PkiSync),
+  isAutoSyncEnabled: z.boolean(),
+  destinationConfig: z.record(z.unknown()),
+  syncOptions: z.record(z.unknown()),
+  projectId: z.string().uuid(),
+  subscriberId: z.string().uuid().nullable().optional(),
+  connectionId: z.string().uuid(),
+  createdAt: z.date(),
+  updatedAt: z.date(),
+  syncStatus: z.string().nullable().optional(),
+  lastSyncedAt: z.date().nullable().optional()
+});

backend/src/services/pki-sync/pki-sync-service.ts

@@ -0,0 +1,447 @@
+import { ForbiddenError, subject } from "@casl/ability";
+
+import { ActionProjectType } from "@app/db/schemas";
+import { TLicenseServiceFactory } from "@app/ee/services/license/license-service";
+import { TPermissionServiceFactory } from "@app/ee/services/permission/permission-service-types";
+import { ProjectPermissionPkiSyncActions, ProjectPermissionSub } from "@app/ee/services/permission/project-permission";
+import { BadRequestError, DatabaseError, NotFoundError } from "@app/lib/errors";
+import { OrgServiceActor } from "@app/lib/types";
+import { AppConnection } from "@app/services/app-connection/app-connection-enums";
+import { TAppConnectionServiceFactory } from "@app/services/app-connection/app-connection-service";
+import { TPkiSubscriberDALFactory } from "@app/services/pki-subscriber/pki-subscriber-dal";
+
+import { TPkiSyncDALFactory } from "./pki-sync-dal";
+import { PkiSync, PkiSyncStatus } from "./pki-sync-enums";
+import { enterprisePkiSyncCheck, getPkiSyncProviderCapabilities, listPkiSyncOptions } from "./pki-sync-fns";
+import { PKI_SYNC_CONNECTION_MAP, PKI_SYNC_NAME_MAP } from "./pki-sync-maps";
+import { TPkiSyncQueueFactory } from "./pki-sync-queue";
+import {
+  TCreatePkiSyncDTO,
+  TDeletePkiSyncDTO,
+  TFindPkiSyncByIdDTO,
+  TListPkiSyncsByProjectId,
+  TPkiSync,
+  TTriggerPkiSyncImportCertificatesByIdDTO,
+  TTriggerPkiSyncRemoveCertificatesByIdDTO,
+  TTriggerPkiSyncSyncCertificatesByIdDTO,
+  TUpdatePkiSyncDTO
+} from "./pki-sync-types";
+
+const getDestinationAppType = (destination: PkiSync): AppConnection => {
+  const appConnection = PKI_SYNC_CONNECTION_MAP[destination];
+  if (!appConnection) {
+    throw new BadRequestError({
+      message: `Unsupported PKI sync destination: ${destination}`
+    });
+  }
+  return appConnection;
+};
+
+type TPkiSyncServiceFactoryDep = {
+  pkiSyncDAL: Pick<
+    TPkiSyncDALFactory,
+    "findById" | "findByProjectIdWithSubscribers" | "findByNameAndProjectId" | "create" | "updateById" | "deleteById"
+  >;
+  pkiSubscriberDAL: Pick<TPkiSubscriberDALFactory, "findById">;
+  appConnectionService: Pick<TAppConnectionServiceFactory, "connectAppConnectionById">;
+  permissionService: Pick<TPermissionServiceFactory, "getProjectPermission">;
+  licenseService: Pick<TLicenseServiceFactory, "getPlan">;
+  pkiSyncQueue: Pick<
+    TPkiSyncQueueFactory,
+    "queuePkiSyncSyncCertificatesById" | "queuePkiSyncImportCertificatesById" | "queuePkiSyncRemoveCertificatesById"
+  >;
+};
+
+export type TPkiSyncServiceFactory = ReturnType<typeof pkiSyncServiceFactory>;
+
+export const pkiSyncServiceFactory = ({
+  pkiSyncDAL,
+  pkiSubscriberDAL,
+  appConnectionService,
+  permissionService,
+  licenseService,
+  pkiSyncQueue
+}: TPkiSyncServiceFactoryDep) => {
+  const createPkiSync = async (
+    {
+      name,
+      description,
+      destination,
+      isAutoSyncEnabled = true,
+      destinationConfig,
+      syncOptions = {},
+      subscriberId,
+      connectionId,
+      projectId
+    }: Omit<TCreatePkiSyncDTO, "auditLogInfo">,
+    actor: OrgServiceActor
+  ): Promise<TPkiSync> => {
+    await enterprisePkiSyncCheck(licenseService, actor.orgId, destination);
+
+    const { permission } = await permissionService.getProjectPermission({
+      actor: actor.type,
+      actorId: actor.id,
+      actorAuthMethod: actor.authMethod,
+      actorOrgId: actor.orgId,
+      actionProjectType: ActionProjectType.CertificateManager,
+      projectId
+    });
+
+    let subscriber;
+    if (subscriberId) {
+      subscriber = await pkiSubscriberDAL.findById(subscriberId);
+      if (!subscriber || subscriber.projectId !== projectId) {
+        throw new NotFoundError({ message: "PKI subscriber not found" });
+      }
+    }
+
+    ForbiddenError.from(permission).throwUnlessCan(
+      ProjectPermissionPkiSyncActions.Create,
+      subscriber
+        ? subject(ProjectPermissionSub.PkiSyncs, { subscriberName: subscriber.name })
+        : ProjectPermissionSub.PkiSyncs
+    );
+
+    // Get the destination app type based on PKI sync destination
+    const destinationApp = getDestinationAppType(destination);
+
+    // Validates permission to connect and app is valid for sync destination
+    await appConnectionService.connectAppConnectionById(destinationApp, connectionId, actor);
+
+    const providerCapabilities = getPkiSyncProviderCapabilities(destination);
+    const resolvedSyncOptions = {
+      ...providerCapabilities,
+      ...syncOptions
+    };
+
+    try {
+      const pkiSync = await pkiSyncDAL.create({
+        name,
+        description,
+        destination,
+        isAutoSyncEnabled,
+        destinationConfig,
+        syncOptions: resolvedSyncOptions,
+        subscriberId,
+        connectionId,
+        projectId,
+        ...(isAutoSyncEnabled && { syncStatus: PkiSyncStatus.Pending })
+      });
+
+      if (pkiSync.isAutoSyncEnabled) {
+        await pkiSyncQueue.queuePkiSyncSyncCertificatesById({ syncId: pkiSync.id });
+      }
+
+      return pkiSync as TPkiSync;
+    } catch (err) {
+      if (err instanceof DatabaseError && (err.error as { code: string })?.code === "23505") {
+        throw new BadRequestError({
+          message: `A PKI Sync with the name "${name}" already exists for the project with ID "${projectId}"`
+        });
+      }
+      throw err;
+    }
+  };
+
+  const updatePkiSync = async (
+    {
+      id,
+      name,
+      description,
+      isAutoSyncEnabled,
+      destinationConfig,
+      syncOptions,
+      subscriberId,
+      connectionId
+    }: Omit<TUpdatePkiSyncDTO, "auditLogInfo" | "projectId">,
+    actor: OrgServiceActor
+  ): Promise<TPkiSync> => {
+    const pkiSync = await pkiSyncDAL.findById(id);
+    if (!pkiSync) throw new NotFoundError({ message: "PKI sync not found" });
+
+    const { permission } = await permissionService.getProjectPermission({
+      actor: actor.type,
+      actorId: actor.id,
+      actorAuthMethod: actor.authMethod,
+      actorOrgId: actor.orgId,
+      actionProjectType: ActionProjectType.CertificateManager,
+      projectId: pkiSync.projectId
+    });
+
+    let currentSubscriber;
+    if (pkiSync.subscriberId) {
+      currentSubscriber = await pkiSubscriberDAL.findById(pkiSync.subscriberId);
+    }
+
+    ForbiddenError.from(permission).throwUnlessCan(
+      ProjectPermissionPkiSyncActions.Edit,
+      currentSubscriber
+        ? subject(ProjectPermissionSub.PkiSyncs, { subscriberName: currentSubscriber.name })
+        : ProjectPermissionSub.PkiSyncs
+    );
+
+    if (name && name !== pkiSync.name) {
+      const existingPkiSync = await pkiSyncDAL.findByNameAndProjectId(name, pkiSync.projectId);
+      if (existingPkiSync) {
+        throw new BadRequestError({ message: "PKI sync with this name already exists" });
+      }
+    }
+
+    if (subscriberId) {
+      const subscriber = await pkiSubscriberDAL.findById(subscriberId);
+      if (!subscriber || subscriber.projectId !== pkiSync.projectId) {
+        throw new NotFoundError({ message: "PKI subscriber not found" });
+      }
+    }
+
+    if (connectionId && connectionId !== pkiSync.connectionId) {
+      const destinationApp = getDestinationAppType(pkiSync.destination);
+      await appConnectionService.connectAppConnectionById(destinationApp, connectionId, actor);
+    }
+
+    let resolvedSyncOptions = syncOptions;
+    if (syncOptions) {
+      const providerCapabilities = getPkiSyncProviderCapabilities(pkiSync.destination);
+
+      if (syncOptions.canImportCertificates && !providerCapabilities.canImportCertificates) {
+        throw new BadRequestError({
+          message: `Certificate import is not supported for ${PKI_SYNC_NAME_MAP[pkiSync.destination]} PKI sync destination`
+        });
+      }
+
+      if (syncOptions.canRemoveCertificates && !providerCapabilities.canRemoveCertificates) {
+        throw new BadRequestError({
+          message: `Certificate removal cannot be enabled for ${PKI_SYNC_NAME_MAP[pkiSync.destination]} PKI sync destination`
+        });
+      }
+
+      resolvedSyncOptions = {
+        ...providerCapabilities,
+        ...syncOptions
+      };
+    }
+
+    const updatedPkiSync = await pkiSyncDAL.updateById(id, {
+      name,
+      description,
+      isAutoSyncEnabled,
+      destinationConfig,
+      syncOptions: resolvedSyncOptions,
+      subscriberId,
+      connectionId
+    });
+
+    return updatedPkiSync as TPkiSync;
+  };
+
+  const deletePkiSync = async (
+    { id }: Omit<TDeletePkiSyncDTO, "auditLogInfo" | "projectId">,
+    actor: OrgServiceActor
+  ) => {
+    const pkiSync = await pkiSyncDAL.findById(id);
+    if (!pkiSync) throw new NotFoundError({ message: "PKI sync not found" });
+
+    const { permission } = await permissionService.getProjectPermission({
+      actor: actor.type,
+      actorId: actor.id,
+      actorAuthMethod: actor.authMethod,
+      actorOrgId: actor.orgId,
+      actionProjectType: ActionProjectType.CertificateManager,
+      projectId: pkiSync.projectId
+    });
+
+    let pkiSyncSubscriber;
+    if (pkiSync.subscriberId) {
+      pkiSyncSubscriber = await pkiSubscriberDAL.findById(pkiSync.subscriberId);
+    }
+
+    ForbiddenError.from(permission).throwUnlessCan(
+      ProjectPermissionPkiSyncActions.Delete,
+      pkiSyncSubscriber
+        ? subject(ProjectPermissionSub.PkiSyncs, { subscriberName: pkiSyncSubscriber.name })
+        : ProjectPermissionSub.PkiSyncs
+    );
+
+    return pkiSyncDAL.deleteById(id);
+  };
+
+  const listPkiSyncsByProjectId = async (
+    { projectId }: TListPkiSyncsByProjectId,
+    actor: OrgServiceActor
+  ): Promise<TPkiSync[]> => {
+    const { permission } = await permissionService.getProjectPermission({
+      actor: actor.type,
+      actorId: actor.id,
+      actorAuthMethod: actor.authMethod,
+      actorOrgId: actor.orgId,
+      actionProjectType: ActionProjectType.CertificateManager,
+      projectId
+    });
+
+    ForbiddenError.from(permission).throwUnlessCan(ProjectPermissionPkiSyncActions.Read, ProjectPermissionSub.PkiSyncs);
+
+    const pkiSyncsWithSubscribers = await pkiSyncDAL.findByProjectIdWithSubscribers(projectId);
+
+    return pkiSyncsWithSubscribers as TPkiSync[];
+  };
+
+  const findPkiSyncById = async ({ id, projectId }: TFindPkiSyncByIdDTO, actor: OrgServiceActor) => {
+    const pkiSync = await pkiSyncDAL.findById(id);
+    if (!pkiSync || (projectId && pkiSync.projectId !== projectId)) {
+      throw new NotFoundError({
+        message: `Could not find PKI Sync with ID "${id}"`
+      });
+    }
+
+    const { permission } = await permissionService.getProjectPermission({
+      actor: actor.type,
+      actorId: actor.id,
+      actorAuthMethod: actor.authMethod,
+      actorOrgId: actor.orgId,
+      actionProjectType: ActionProjectType.CertificateManager,
+      projectId: pkiSync.projectId
+    });
+
+    let findSubscriber;
+    if (pkiSync.subscriberId) {
+      findSubscriber = await pkiSubscriberDAL.findById(pkiSync.subscriberId);
+    }
+
+    ForbiddenError.from(permission).throwUnlessCan(
+      ProjectPermissionPkiSyncActions.Read,
+      findSubscriber
+        ? subject(ProjectPermissionSub.PkiSyncs, { subscriberName: findSubscriber.name })
+        : ProjectPermissionSub.PkiSyncs
+    );
+
+    const result = {
+      ...pkiSync,
+      subscriber: findSubscriber ? { id: findSubscriber.id, name: findSubscriber.name } : null
+    } as TPkiSync;
+
+    return result;
+  };
+
+  const triggerPkiSyncSyncCertificatesById = async (
+    { id }: Omit<TTriggerPkiSyncSyncCertificatesByIdDTO, "auditLogInfo" | "projectId">,
+    actor: OrgServiceActor
+  ) => {
+    const pkiSync = await pkiSyncDAL.findById(id);
+    if (!pkiSync) throw new NotFoundError({ message: "PKI sync not found" });
+
+    const { permission } = await permissionService.getProjectPermission({
+      actor: actor.type,
+      actorId: actor.id,
+      actorAuthMethod: actor.authMethod,
+      actorOrgId: actor.orgId,
+      actionProjectType: ActionProjectType.CertificateManager,
+      projectId: pkiSync.projectId
+    });
+
+    let syncSubscriber;
+    if (pkiSync.subscriberId) {
+      syncSubscriber = await pkiSubscriberDAL.findById(pkiSync.subscriberId);
+    }
+
+    ForbiddenError.from(permission).throwUnlessCan(
+      ProjectPermissionPkiSyncActions.SyncCertificates,
+      syncSubscriber
+        ? subject(ProjectPermissionSub.PkiSyncs, { subscriberName: syncSubscriber.name })
+        : ProjectPermissionSub.PkiSyncs
+    );
+
+    await pkiSyncQueue.queuePkiSyncSyncCertificatesById({ syncId: id });
+
+    return { message: "PKI sync job added to queue successfully" };
+  };
+
+  const triggerPkiSyncImportCertificatesById = async (
+    { id }: Omit<TTriggerPkiSyncImportCertificatesByIdDTO, "auditLogInfo" | "projectId">,
+    actor: OrgServiceActor
+  ) => {
+    const pkiSync = await pkiSyncDAL.findById(id);
+    if (!pkiSync) throw new NotFoundError({ message: "PKI sync not found" });
+
+    const { permission } = await permissionService.getProjectPermission({
+      actor: actor.type,
+      actorId: actor.id,
+      actorAuthMethod: actor.authMethod,
+      actorOrgId: actor.orgId,
+      actionProjectType: ActionProjectType.CertificateManager,
+      projectId: pkiSync.projectId
+    });
+
+    // Check if the PKI sync destination supports importing certificates
+    const syncOptions = listPkiSyncOptions().find((option) => option.destination === pkiSync.destination);
+    if (!syncOptions?.canImportCertificates) {
+      throw new BadRequestError({
+        message: `Certificate import is not supported for ${pkiSync.destination} PKI sync destination`
+      });
+    }
+
+    let importSubscriber;
+    if (pkiSync.subscriberId) {
+      importSubscriber = await pkiSubscriberDAL.findById(pkiSync.subscriberId);
+    }
+
+    ForbiddenError.from(permission).throwUnlessCan(
+      ProjectPermissionPkiSyncActions.ImportCertificates,
+      importSubscriber
+        ? subject(ProjectPermissionSub.PkiSyncs, { subscriberName: importSubscriber.name })
+        : ProjectPermissionSub.PkiSyncs
+    );
+
+    await pkiSyncQueue.queuePkiSyncImportCertificatesById({ syncId: id });
+
+    return { message: "PKI sync import job added to queue successfully" };
+  };
+
+  const triggerPkiSyncRemoveCertificatesById = async (
+    { id }: Omit<TTriggerPkiSyncRemoveCertificatesByIdDTO, "auditLogInfo" | "projectId">,
+    actor: OrgServiceActor
+  ) => {
+    const pkiSync = await pkiSyncDAL.findById(id);
+    if (!pkiSync) throw new NotFoundError({ message: "PKI sync not found" });
+
+    const { permission } = await permissionService.getProjectPermission({
+      actor: actor.type,
+      actorId: actor.id,
+      actorAuthMethod: actor.authMethod,
+      actorOrgId: actor.orgId,
+      actionProjectType: ActionProjectType.CertificateManager,
+      projectId: pkiSync.projectId
+    });
+
+    let removeSubscriber;
+    if (pkiSync.subscriberId) {
+      removeSubscriber = await pkiSubscriberDAL.findById(pkiSync.subscriberId);
+    }
+
+    ForbiddenError.from(permission).throwUnlessCan(
+      ProjectPermissionPkiSyncActions.RemoveCertificates,
+      removeSubscriber
+        ? subject(ProjectPermissionSub.PkiSyncs, { subscriberName: removeSubscriber.name })
+        : ProjectPermissionSub.PkiSyncs
+    );
+
+    await pkiSyncQueue.queuePkiSyncRemoveCertificatesById({ syncId: id });
+
+    return { message: "PKI sync remove job added to queue successfully" };
+  };
+
+  const getPkiSyncOptions = () => {
+    return listPkiSyncOptions();
+  };
+
+  return {
+    createPkiSync,
+    updatePkiSync,
+    deletePkiSync,
+    listPkiSyncsByProjectId,
+    findPkiSyncById,
+    triggerPkiSyncSyncCertificatesById,
+    triggerPkiSyncImportCertificatesById,
+    triggerPkiSyncRemoveCertificatesById,
+    getPkiSyncOptions
+  };
+};

backend/src/services/pki-sync/pki-sync-types.ts

@@ -0,0 +1,169 @@
+import { Job } from "bullmq";
+
+import { AuditLogInfo } from "@app/ee/services/audit-log/audit-log-types";
+import { QueueJobs } from "@app/queue";
+import { ResourceMetadataDTO } from "@app/services/resource-metadata/resource-metadata-schema";
+
+import { TPkiSyncDALFactory } from "./pki-sync-dal";
+import { PkiSync } from "./pki-sync-enums";
+
+export type TPkiSync = {
+  id: string;
+  name: string;
+  description?: string;
+  destination: PkiSync;
+  isAutoSyncEnabled: boolean;
+  destinationConfig: Record<string, unknown>;
+  syncOptions: Record<string, unknown>;
+  projectId: string;
+  subscriberId?: string;
+  connectionId: string;
+  createdAt: Date;
+  updatedAt: Date;
+  syncStatus?: string;
+  lastSyncJobId?: string;
+  lastSyncMessage?: string;
+  lastSyncedAt?: Date;
+  importStatus?: string;
+  lastImportJobId?: string;
+  lastImportMessage?: string;
+  lastImportedAt?: Date;
+  removeStatus?: string;
+  lastRemoveJobId?: string;
+  lastRemoveMessage?: string;
+  lastRemovedAt?: Date;
+  appConnectionName: string;
+  appConnectionApp: string;
+  connection: {
+    id: string;
+    name: string;
+    app: string;
+    encryptedCredentials: unknown;
+    orgId: string;
+    projectId?: string;
+    method: string;
+    description?: string;
+    version: number;
+    gatewayId?: string;
+    createdAt: Date;
+    updatedAt: Date;
+    isPlatformManagedCredentials?: boolean;
+  };
+  subscriber?: {
+    id: string;
+    name: string;
+  } | null;
+};
+
+export type TPkiSyncWithCredentials = TPkiSync & {
+  connection: {
+    id: string;
+    name: string;
+    app: string;
+    credentials: Record<string, unknown>;
+    orgId: string;
+  };
+};
+
+export type TPkiSyncListItem = TPkiSync & {
+  appConnectionName: string;
+  appConnectionApp: string;
+};
+
+export type TCertificateMap = Record<string, { cert: string; privateKey: string; certificateChain?: string }>;
+
+export type TCreatePkiSyncDTO = {
+  name: string;
+  description?: string;
+  destination: PkiSync;
+  isAutoSyncEnabled?: boolean;
+  destinationConfig: Record<string, unknown>;
+  syncOptions?: Record<string, unknown>;
+  subscriberId?: string;
+  connectionId: string;
+  projectId: string;
+  auditLogInfo: AuditLogInfo;
+  resourceMetadata?: ResourceMetadataDTO;
+};
+
+export type TUpdatePkiSyncDTO = {
+  id: string;
+  projectId?: string;
+  name?: string;
+  description?: string;
+  isAutoSyncEnabled?: boolean;
+  destinationConfig?: Record<string, unknown>;
+  syncOptions?: Record<string, unknown>;
+  subscriberId?: string;
+  connectionId?: string;
+  auditLogInfo: AuditLogInfo;
+  resourceMetadata?: ResourceMetadataDTO;
+};
+
+export type TDeletePkiSyncDTO = {
+  id: string;
+  projectId?: string;
+  auditLogInfo: AuditLogInfo;
+};
+
+export type TListPkiSyncsByProjectId = {
+  projectId: string;
+};
+
+export type TFindPkiSyncByIdDTO = {
+  id: string;
+  projectId?: string;
+};
+
+export type TTriggerPkiSyncSyncCertificatesByIdDTO = {
+  id: string;
+  projectId?: string;
+  auditLogInfo: AuditLogInfo;
+};
+
+export type TTriggerPkiSyncImportCertificatesByIdDTO = {
+  id: string;
+  projectId?: string;
+  auditLogInfo: AuditLogInfo;
+};
+
+export type TTriggerPkiSyncRemoveCertificatesByIdDTO = {
+  id: string;
+  projectId?: string;
+  auditLogInfo: AuditLogInfo;
+};
+
+export type TPkiSyncRaw = NonNullable<Awaited<ReturnType<TPkiSyncDALFactory["findById"]>>>;
+
+export type TQueuePkiSyncSyncCertificatesByIdDTO = {
+  syncId: string;
+  failedToAcquireLockCount?: number;
+  auditLogInfo?: AuditLogInfo;
+};
+
+export type TQueuePkiSyncImportCertificatesByIdDTO = {
+  syncId: string;
+  auditLogInfo?: AuditLogInfo;
+};
+
+export type TQueuePkiSyncRemoveCertificatesByIdDTO = {
+  syncId: string;
+  auditLogInfo?: AuditLogInfo;
+  deleteSyncOnComplete?: boolean;
+};
+
+export type TPkiSyncSyncCertificatesDTO = Job<
+  TQueuePkiSyncSyncCertificatesByIdDTO,
+  void,
+  QueueJobs.PkiSyncSyncCertificates
+>;
+export type TPkiSyncImportCertificatesDTO = Job<
+  TQueuePkiSyncImportCertificatesByIdDTO,
+  void,
+  QueueJobs.PkiSyncImportCertificates
+>;
+export type TPkiSyncRemoveCertificatesDTO = Job<
+  TQueuePkiSyncRemoveCertificatesByIdDTO,
+  void,
+  QueueJobs.PkiSyncRemoveCertificates
+>;

backend/src/services/pki-sync/pki-sync-utils.ts

@@ -0,0 +1,27 @@
+import { logger } from "@app/lib/logger";
+
+import { TPkiSyncDALFactory } from "./pki-sync-dal";
+import { TPkiSyncQueueFactory } from "./pki-sync-queue";
+
+export const triggerAutoSyncForSubscriber = async (
+  subscriberId: string,
+  dependencies: {
+    pkiSyncDAL: Pick<TPkiSyncDALFactory, "find">;
+    pkiSyncQueue: Pick<TPkiSyncQueueFactory, "queuePkiSyncSyncCertificatesById">;
+  }
+) => {
+  try {
+    const pkiSyncs = await dependencies.pkiSyncDAL.find({
+      subscriberId,
+      isAutoSyncEnabled: true
+    });
+
+    // Queue sync jobs for each auto sync enabled PKI sync
+    const syncPromises = pkiSyncs.map((pkiSync) =>
+      dependencies.pkiSyncQueue.queuePkiSyncSyncCertificatesById({ syncId: pkiSync.id })
+    );
+    await Promise.all(syncPromises);
+  } catch (error) {
+    logger.error(error, `Failed to trigger auto sync for subscriber ${subscriberId}:`);
+  }
+};

backend/src/services/project-membership/project-membership-service.ts

@@ -43,7 +43,10 @@ import {
 import { TProjectUserMembershipRoleDALFactory } from "./project-user-membership-role-dal";
 
 type TProjectMembershipServiceFactoryDep = {
-  permissionService: Pick<TPermissionServiceFactory, "getProjectPermission" | "getProjectPermissionByRole">;
+  permissionService: Pick<
+    TPermissionServiceFactory,
+    "getProjectPermission" | "getProjectPermissionByRole" | "invalidateProjectPermissionCache"
+  >;
   smtpService: TSmtpService;
   projectBotDAL: TProjectBotDALFactory;
   projectMembershipDAL: TProjectMembershipDALFactory;
@@ -239,6 +242,8 @@ export const projectMembershipServiceFactory = ({
       );
     });
 
+    await permissionService.invalidateProjectPermissionCache(projectId);
+
     if (sendEmails) {
       await notificationService.createUserNotifications(
         orgMembers.map((member) => ({
@@ -371,6 +376,8 @@ export const projectMembershipServiceFactory = ({
       return projectUserMembershipRoleDAL.insertMany(sanitizedProjectMembershipRoles, tx);
     });
 
+    await permissionService.invalidateProjectPermissionCache(projectId);
+
     return updatedRoles;
   };
 
@@ -414,6 +421,9 @@ export const projectMembershipServiceFactory = ({
       );
       return deletedMembership;
     });
+
+    await permissionService.invalidateProjectPermissionCache(projectId);
+
     return membership;
   };
 
@@ -515,6 +525,9 @@ export const projectMembershipServiceFactory = ({
 
       return deletedMemberships;
     });
+
+    await permissionService.invalidateProjectPermissionCache(projectId);
+
     return memberships;
   };
 

backend/src/services/project-role/project-role-service.ts

@@ -35,7 +35,10 @@ type TProjectRoleServiceFactoryDep = {
   identityDAL: Pick<TIdentityDALFactory, "findById">;
   userDAL: Pick<TUserDALFactory, "findById">;
   projectDAL: Pick<TProjectDALFactory, "findProjectBySlug" | "findProjectById">;
-  permissionService: Pick<TPermissionServiceFactory, "getProjectPermission" | "getUserProjectPermission">;
+  permissionService: Pick<
+    TPermissionServiceFactory,
+    "getProjectPermission" | "getUserProjectPermission" | "invalidateProjectPermissionCache"
+  >;
   identityProjectMembershipRoleDAL: TIdentityProjectMembershipRoleDALFactory;
   projectUserMembershipRoleDAL: TProjectUserMembershipRoleDALFactory;
 };
@@ -162,6 +165,8 @@ export const projectRoleServiceFactory = ({
     });
     if (!updatedRole) throw new NotFoundError({ message: "Project role not found", name: "Update role" });
 
+    await permissionService.invalidateProjectPermissionCache(projectRole.projectId);
+
     return { ...updatedRole, permissions: unpackPermissions(updatedRole.permissions) };
   };
 
@@ -197,6 +202,8 @@ export const projectRoleServiceFactory = ({
     const deletedRole = await projectRoleDAL.deleteById(roleId);
     if (!deletedRole) throw new NotFoundError({ message: "Project role not found", name: "Delete role" });
 
+    await permissionService.invalidateProjectPermissionCache(projectRole.projectId);
+
     return { ...deletedRole, permissions: unpackPermissions(deletedRole.permissions) };
   };
 

backend/src/services/secret-v2-bridge/secret-v2-bridge-dal.ts

@@ -446,9 +446,10 @@ export const secretV2BridgeDALFactory = ({ db, keyStore }: TSecretV2DalArg) => {
           }
         })
         .where((bd) => {
-          void bd
-            .whereNull(`${TableName.SecretV2}.userId`)
-            .orWhere({ [`${TableName.SecretV2}.userId` as "userId"]: userId || null });
+          void bd.whereNull(`${TableName.SecretV2}.userId`);
+          // scott: removing this as we don't need to count overrides
+          // and there is currently a bug when you move secrets that doesn't move the override so this can skew count
+          // .orWhere({ [`${TableName.SecretV2}.userId` as "userId"]: userId || null });
         })
         .countDistinct(`${TableName.SecretV2}.key`);
 

backend/src/services/secret-v2-bridge/secret-v2-bridge-fns.ts

@@ -597,19 +597,27 @@ export const expandSecretReferencesFactory = ({
       return secretCache[cacheKey][secretKey] || { value: "", tags: [] };
     }
 
-    const folder = await folderDAL.findBySecretPath(projectId, environment, secretPath);
-    if (!folder) return { value: "", tags: [] };
-    const secrets = await secretDAL.findByFolderId({ folderId: folder.id });
+    try {
+      const folder = await folderDAL.findBySecretPath(projectId, environment, secretPath);
+      if (!folder) return { value: "", tags: [] };
+      const secrets = await secretDAL.findByFolderId({ folderId: folder.id });
 
-    const decryptedSecret = secrets.reduce<Record<string, { value: string; tags: string[] }>>((prev, secret) => {
-      // eslint-disable-next-line no-param-reassign
-      prev[secret.key] = { value: decryptSecret(secret.encryptedValue) || "", tags: secret.tags?.map((el) => el.slug) };
-      return prev;
-    }, {});
+      const decryptedSecret = secrets.reduce<Record<string, { value: string; tags: string[] }>>((prev, secret) => {
+        // eslint-disable-next-line no-param-reassign
+        prev[secret.key] = {
+          value: decryptSecret(secret.encryptedValue) || "",
+          tags: secret.tags?.map((el) => el.slug)
+        };
+        return prev;
+      }, {});
 
-    secretCache[cacheKey] = decryptedSecret;
+      secretCache[cacheKey] = decryptedSecret;
 
-    return secretCache[cacheKey][secretKey] || { value: "", tags: [] };
+      return secretCache[cacheKey][secretKey] || { value: "", tags: [] };
+    } catch (error) {
+      secretCache[cacheKey] = {};
+      return { value: "", tags: [] };
+    }
   };
 
   const recursivelyExpandSecret = async (dto: {
@@ -622,11 +630,16 @@ export const expandSecretReferencesFactory = ({
     const stackTrace = { ...dto, key: "root", children: [] } as TSecretReferenceTraceNode;
 
     if (!dto.value) return { expandedValue: "", stackTrace };
-    const stack = [{ ...dto, depth: 0, trace: stackTrace }];
+
+    // Track visited secrets to prevent circular references
+    const createSecretId = (env: string, secretPath: string, key: string) => `${env}:${secretPath}:${key}`;
+
+    const currentSecretId = createSecretId(dto.environment, dto.secretPath, dto.secretKey);
+    const stack = [{ ...dto, depth: 0, trace: stackTrace, visitedSecrets: new Set<string>([currentSecretId]) }];
     let expandedValue = dto.value;
 
     while (stack.length) {
-      const { value, secretPath, environment, depth, trace } = stack.pop()!;
+      const { value, secretPath, environment, depth, trace, visitedSecrets } = stack.pop()!;
 
       // eslint-disable-next-line no-continue
       if (depth > MAX_SECRET_REFERENCE_DEPTH) continue;
@@ -664,6 +677,7 @@ export const expandSecretReferencesFactory = ({
               });
 
             const cacheKey = getCacheUniqueKey(environment, secretPath);
+            if (!secretCache[cacheKey]) secretCache[cacheKey] = {};
             secretCache[cacheKey][secretKey] = referredValue;
 
             referencedSecretValue = referredValue.value;
@@ -683,6 +697,7 @@ export const expandSecretReferencesFactory = ({
               });
 
             const cacheKey = getCacheUniqueKey(secretReferenceEnvironment, secretReferencePath);
+            if (!secretCache[cacheKey]) secretCache[cacheKey] = {};
             secretCache[cacheKey][secretReferenceKey] = referedValue;
 
             referencedSecretValue = referedValue.value;
@@ -700,17 +715,27 @@ export const expandSecretReferencesFactory = ({
             trace
           };
 
-          const shouldExpandMore = INTERPOLATION_TEST_REGEX.test(referencedSecretValue);
+          // Check for circular reference
+          const referencedSecretId = createSecretId(
+            referencedSecretEnvironmentSlug,
+            referencedSecretPath,
+            referencedSecretKey
+          );
+          const isCircular = visitedSecrets.has(referencedSecretId);
+
+          const newVisitedSecrets = new Set([...visitedSecrets, referencedSecretId]);
+
+          const shouldExpandMore = INTERPOLATION_TEST_REGEX.test(referencedSecretValue) && !isCircular;
           if (dto.shouldStackTrace) {
             const stackTraceNode = { ...node, children: [], key: referencedSecretKey, trace: null };
             trace?.children.push(stackTraceNode);
             // if stack trace this would be child node
             if (shouldExpandMore) {
-              stack.push({ ...node, trace: stackTraceNode });
+              stack.push({ ...node, trace: stackTraceNode, visitedSecrets: newVisitedSecrets });
             }
           } else if (shouldExpandMore) {
             // if no stack trace is needed we just keep going with root node
-            stack.push(node);
+            stack.push({ ...node, visitedSecrets: newVisitedSecrets });
           }
 
           if (referencedSecretValue) {
@@ -757,7 +782,7 @@ export const expandSecretReferencesFactory = ({
 };
 
 export const reshapeBridgeSecret = (
-  workspaceId: string,
+  projectId: string,
   environment: string,
   secretPath: string,
   secret: Omit<TSecretsV2, "encryptedValue" | "encryptedComment"> & {
@@ -784,7 +809,8 @@ export const reshapeBridgeSecret = (
 ) => ({
   secretKey: secret.key,
   secretPath,
-  workspace: workspaceId,
+  workspace: projectId,
+  projectId,
   environment,
   secretComment: secret.comment || "",
   version: secret.version,

backend/src/services/secret-v2-bridge/secret-v2-bridge-service.ts

@@ -159,17 +159,14 @@ export const secretV2BridgeServiceFactory = ({
     const uniqueReferenceEnvironmentSlugs = Array.from(new Set(references.map((el) => el.environment)));
     const referencesEnvironments = await projectEnvDAL.findBySlugs(projectId, uniqueReferenceEnvironmentSlugs, tx);
 
-    if (referencesEnvironments.length !== uniqueReferenceEnvironmentSlugs.length)
-      throw new BadRequestError({
-        message: `Referenced environment not found. Missing ${diff(
-          uniqueReferenceEnvironmentSlugs,
-          referencesEnvironments.map((el) => el.slug)
-        ).join(",")}`
-      });
-
+    // Filter out references to non-existent environments
     const referencesEnvironmentGroupBySlug = groupBy(referencesEnvironments, (i) => i.slug);
+    const validEnvironmentReferences = references.filter((el) => referencesEnvironmentGroupBySlug[el.environment]);
+
+    if (validEnvironmentReferences.length === 0) return;
+
     const referredFolders = await folderDAL.findByManySecretPath(
-      references.map((el) => ({
+      validEnvironmentReferences.map((el) => ({
         secretPath: el.secretPath,
         envId: referencesEnvironmentGroupBySlug[el.environment][0].id
       })),
@@ -177,58 +174,71 @@ export const secretV2BridgeServiceFactory = ({
     );
 
     const referencesFolderGroupByPath = groupBy(referredFolders.filter(Boolean), (i) => `${i?.envId}-${i?.path}`);
+
+    // Find only references that have valid folders (don't throw for missing paths)
+    const validReferences = validEnvironmentReferences.filter((el) => {
+      const folderId =
+        referencesFolderGroupByPath[`${referencesEnvironmentGroupBySlug[el.environment][0].id}-${el.secretPath}`]?.[0]
+          ?.id;
+      return folderId;
+    });
+
+    if (validReferences.length === 0) return;
+
     const referredSecrets = await secretDAL.find(
       {
         $complex: {
           operator: "or",
-          value: references.map((el) => {
-            const folderId =
-              referencesFolderGroupByPath[
-                `${referencesEnvironmentGroupBySlug[el.environment][0].id}-${el.secretPath}`
-              ][0]?.id;
-            if (!folderId) throw new BadRequestError({ message: `Referenced path ${el.secretPath} doesn't exist` });
+          value: validReferences
+            .map((el) => {
+              const folderGroup =
+                referencesFolderGroupByPath[
+                  `${referencesEnvironmentGroupBySlug[el.environment][0].id}-${el.secretPath}`
+                ];
+              if (!folderGroup || !folderGroup[0]) return null;
 
-            return {
-              operator: "and",
-              value: [
-                {
-                  operator: "eq",
-                  field: "folderId",
-                  value: folderId
-                },
-                {
-                  operator: "eq",
-                  field: `${TableName.SecretV2}.key` as "key",
-                  value: el.secretKey
-                }
-              ]
-            };
-          })
+              const folderId = folderGroup[0].id;
+
+              return {
+                operator: "and",
+                value: [
+                  {
+                    operator: "eq",
+                    field: "folderId",
+                    value: folderId
+                  },
+                  {
+                    operator: "eq",
+                    field: `${TableName.SecretV2}.key` as "key",
+                    value: el.secretKey
+                  }
+                ]
+              };
+            })
+            .filter((query) => query !== null) as Array<{
+            operator: "and";
+            value: Array<{
+              operator: "eq";
+              field: "folderId" | "key";
+              value: string;
+            }>;
+          }>
         }
       },
       { tx }
     );
 
-    if (
-      referredSecrets.length !==
-      new Set(references.map(({ secretKey, secretPath, environment }) => `${secretKey}.${secretPath}.${environment}`))
-        .size // only count unique references
-    )
-      throw new BadRequestError({
-        message: `Referenced secret(s) not found: ${diff(
-          references.map((el) => el.secretKey),
-          referredSecrets.map((el) => el.key)
-        ).join(",")}`
-      });
-
-    const referredSecretsGroupBySecretKey = groupBy(referredSecrets, (i) => i.key);
-    references.forEach((el) => {
-      throwIfMissingSecretReadValueOrDescribePermission(permission, ProjectPermissionSecretActions.DescribeSecret, {
-        environment: el.environment,
-        secretPath: el.secretPath,
-        secretName: el.secretKey,
-        secretTags: referredSecretsGroupBySecretKey[el.secretKey][0]?.tags?.map((i) => i.slug)
-      });
+    // Only check permissions for secrets that actually exist
+    referredSecrets.forEach((secret) => {
+      const reference = validReferences.find((ref) => ref.secretKey === secret.key);
+      if (reference) {
+        throwIfMissingSecretReadValueOrDescribePermission(permission, ProjectPermissionSecretActions.DescribeSecret, {
+          environment: reference.environment,
+          secretPath: reference.secretPath,
+          secretName: reference.secretKey,
+          secretTags: secret.tags?.map((i) => i.slug)
+        });
+      }
     });
 
     return referredSecrets;
@@ -478,15 +488,16 @@ export const secretV2BridgeServiceFactory = ({
       secret = sharedSecretToModify;
     }
 
-    ForbiddenError.from(permission).throwUnlessCan(
-      ProjectPermissionSecretActions.Edit,
-      subject(ProjectPermissionSub.Secrets, {
-        environment,
-        secretPath,
-        secretName: inputSecret.secretName,
-        secretTags: secret.tags.map((el) => el.slug)
-      })
-    );
+    if (secret.type !== SecretType.Personal)
+      ForbiddenError.from(permission).throwUnlessCan(
+        ProjectPermissionSecretActions.Edit,
+        subject(ProjectPermissionSub.Secrets, {
+          environment,
+          secretPath,
+          secretName: inputSecret.secretName,
+          secretTags: secret.tags.map((el) => el.slug)
+        })
+      );
 
     // validate tags
     // fetch all tags and if not same count throw error meaning one was invalid tags
@@ -497,17 +508,18 @@ export const secretV2BridgeServiceFactory = ({
     const tagsToCheck = inputSecret.tagIds ? newTags : secret.tags;
 
     // now check with new ids
-    ForbiddenError.from(permission).throwUnlessCan(
-      ProjectPermissionSecretActions.Edit,
-      subject(ProjectPermissionSub.Secrets, {
-        environment,
-        secretPath,
-        secretName: inputSecret.secretName,
-        ...(tagsToCheck.length && {
-          secretTags: tagsToCheck.map((el) => el.slug)
+    if (secret.type !== SecretType.Personal)
+      ForbiddenError.from(permission).throwUnlessCan(
+        ProjectPermissionSecretActions.Edit,
+        subject(ProjectPermissionSub.Secrets, {
+          environment,
+          secretPath,
+          secretName: inputSecret.secretName,
+          ...(tagsToCheck.length && {
+            secretTags: tagsToCheck.map((el) => el.slug)
+          })
         })
-      })
-    );
+      );
 
     if (inputSecret.newSecretName) {
       const doesNewNameSecretExist = await secretDAL.findOne({
@@ -546,6 +558,14 @@ export const secretV2BridgeServiceFactory = ({
       );
     }
 
+    if (secretValue) {
+      const { nestedReferences, localReferences } = getAllSecretReferences(secretValue);
+      const allSecretReferences = nestedReferences.concat(
+        localReferences.map((el) => ({ secretKey: el, secretPath, environment }))
+      );
+      await $validateSecretReferences(projectId, permission, allSecretReferences);
+    }
+
     const { encryptor: secretManagerEncryptor } = await kmsService.createCipherPairWithDataKey({
       type: KmsDataKey.SecretManager,
       projectId
@@ -706,15 +726,17 @@ export const secretV2BridgeServiceFactory = ({
           })
     });
     if (!secretToDelete) throw new NotFoundError({ message: "Secret not found" });
-    ForbiddenError.from(permission).throwUnlessCan(
-      ProjectPermissionSecretActions.Delete,
-      subject(ProjectPermissionSub.Secrets, {
-        environment,
-        secretPath,
-        secretName: secretToDelete.key,
-        secretTags: secretToDelete.tags?.map((el) => el.slug)
-      })
-    );
+
+    if (secretToDelete.type !== SecretType.Personal)
+      ForbiddenError.from(permission).throwUnlessCan(
+        ProjectPermissionSecretActions.Delete,
+        subject(ProjectPermissionSub.Secrets, {
+          environment,
+          secretPath,
+          secretName: secretToDelete.key,
+          secretTags: secretToDelete.tags?.map((el) => el.slug)
+        })
+      );
 
     try {
       const deletedSecret = await secretDAL.transaction(async (tx) => {
@@ -1658,7 +1680,7 @@ export const secretV2BridgeServiceFactory = ({
     await scanSecretPolicyViolations(projectId, secretPath, inputSecrets, project.secretDetectionIgnoreValues || []);
 
     // get all tags
-    const sanitizedTagIds = inputSecrets.flatMap(({ tagIds = [] }) => tagIds);
+    const sanitizedTagIds = [...new Set(inputSecrets.flatMap(({ tagIds = [] }) => tagIds))];
     const tags = sanitizedTagIds.length ? await secretTagDAL.findManyTagsById(projectId, sanitizedTagIds) : [];
     if (tags.length !== sanitizedTagIds.length)
       throw new NotFoundError({ message: `Tag not found. Found ${tags.map((el) => el.slug).join(",")}` });
@@ -1906,7 +1928,7 @@ export const secretV2BridgeServiceFactory = ({
         });
 
         // get all tags
-        const sanitizedTagIds = secretsToUpdate.flatMap(({ tagIds = [] }) => tagIds);
+        const sanitizedTagIds = [...new Set(secretsToUpdate.flatMap(({ tagIds = [] }) => tagIds))];
         const tags = sanitizedTagIds.length ? await secretTagDAL.findManyTagsById(projectId, sanitizedTagIds, tx) : [];
         if (tags.length !== sanitizedTagIds.length) throw new NotFoundError({ message: "Tag not found" });
         const tagsGroupByID = groupBy(tags, (i) => i.id);
@@ -2333,7 +2355,8 @@ export const secretV2BridgeServiceFactory = ({
     actorAuthMethod,
     limit = 20,
     offset = 0,
-    secretId
+    secretId,
+    secretVersions: secretVersionsFilter
   }: TGetSecretVersionsDTO) => {
     const secret = await secretDAL.findById(secretId);
 
@@ -2370,6 +2393,7 @@ export const secretV2BridgeServiceFactory = ({
     const secretVersions = await secretVersionDAL.findVersionsBySecretIdWithActors({
       secretId,
       projectId: folder.projectId,
+      secretVersions: secretVersionsFilter,
       findOpt: {
         offset,
         limit,
@@ -2939,7 +2963,7 @@ export const secretV2BridgeServiceFactory = ({
       secretKey: secretName
     });
 
-    return { tree: stackTrace, value: expandedValue };
+    return { tree: stackTrace, value: expandedValue, secret };
   };
 
   const getAccessibleSecrets = async ({
@@ -3155,6 +3179,7 @@ export const secretV2BridgeServiceFactory = ({
     getSecretById,
     getAccessibleSecrets,
     getSecretVersionsByIds,
-    findSecretIdsByFolderIdAndKeys
+    findSecretIdsByFolderIdAndKeys,
+    $validateSecretReferences
   };
 };

backend/src/services/secret-v2-bridge/secret-v2-bridge-types.ts

@@ -159,6 +159,7 @@ export type TGetSecretVersionsDTO = Omit<TProjectPermission, "projectId"> & {
   limit?: number;
   offset?: number;
   secretId: string;
+  secretVersions?: string[];
 };
 
 export type TSecretReference = { environment: string; secretPath: string; secretKey: string };

backend/src/services/secret/secret-service.ts

@@ -2568,7 +2568,8 @@ export const secretServiceFactory = ({
     actorAuthMethod,
     limit = 20,
     offset = 0,
-    secretId
+    secretId,
+    secretVersions: filterSecretVersions
   }: TGetSecretVersionsDTO) => {
     const secretVersionV2 = await secretV2BridgeService
       .getSecretVersions({
@@ -2578,7 +2579,8 @@ export const secretServiceFactory = ({
         actorAuthMethod,
         limit,
         offset,
-        secretId
+        secretId,
+        secretVersions: filterSecretVersions
       })
       .catch((err) => {
         if ((err as Error).message === "BadRequest: Failed to find secret") {

backend/src/services/secret/secret-types.ts

@@ -331,6 +331,7 @@ export type TGetSecretVersionsDTO = Omit<TProjectPermission, "projectId"> & {
   limit?: number;
   offset?: number;
   secretId: string;
+  secretVersions?: string[];
 };
 
 export type TSecretReference = { environment: string; secretPath: string };

backend/src/services/smtp/emails/OAuthPasswordResetTemplate.tsx

@@ -0,0 +1,80 @@
+import { Heading, Section, Text } from "@react-email/components";
+import React from "react";
+
+import { BaseEmailWrapper, BaseEmailWrapperProps } from "./BaseEmailWrapper";
+import { BaseLink } from "./BaseLink";
+
+interface OAuthPasswordResetTemplateProps extends Omit<BaseEmailWrapperProps, "title" | "preview" | "children"> {
+  email: string;
+  lastLoginMethod?: string | null;
+  isCloud: boolean;
+}
+
+export const OAuthPasswordResetTemplate = ({
+  email,
+  lastLoginMethod,
+  isCloud,
+  siteUrl
+}: OAuthPasswordResetTemplateProps) => {
+  const getAuthMethodDisplayName = (method: string) => {
+    return method
+      .split("-")
+      .map((word) => {
+        const upperWord = word.toUpperCase();
+        if (["SAML", "LDAP", "OIDC", "SSO"].includes(upperWord)) {
+          return upperWord;
+        }
+        return word.charAt(0).toUpperCase() + word.slice(1);
+      })
+      .join(" ");
+  };
+
+  const getAuthMethodMessage = () => {
+    if (lastLoginMethod) {
+      const displayName = getAuthMethodDisplayName(lastLoginMethod);
+      return `Please continue by signing in with ${displayName}.`;
+    }
+    return "Please continue using the same authentication method you previously used to sign in (e.g., SSO, SAML, OAuth, or another configured provider).";
+  };
+  return (
+    <BaseEmailWrapper
+      title="Password Reset Not Available"
+      preview="Your account doesn't have password login enabled."
+      siteUrl={siteUrl}
+    >
+      <Heading className="text-black text-[18px] leading-[28px] text-center font-normal p-0 mx-0">
+        <strong>Password Reset Not Available</strong>
+      </Heading>
+      <Section className="px-[24px] mb-[28px] mt-[36px] pt-[12px] pb-[8px] border border-solid border-gray-200 rounded-md bg-gray-50">
+        <Text className="text-[14px]">
+          <strong>Password reset is not available for this account.</strong>
+        </Text>
+        <Text className="text-[14px]">
+          A password reset was requested for your Infisical account ({email}), but password login has not been enabled
+          for your account.
+        </Text>
+        <Text className="text-[14px]">{getAuthMethodMessage()}</Text>
+        <Text className="text-[14px]">
+          If you did not initiate this request, please contact{" "}
+          {isCloud ? (
+            <>
+              us immediately at <BaseLink href="mailto:[email protected]">support@infisical.com</BaseLink>
+            </>
+          ) : (
+            "your administrator immediately"
+          )}
+          .
+        </Text>
+      </Section>
+    </BaseEmailWrapper>
+  );
+};
+
+export default OAuthPasswordResetTemplate;
+
+OAuthPasswordResetTemplate.PreviewProps = {
+  email: "[email protected]",
+  lastLoginMethod: "github",
+  isCloud: true,
+  siteUrl: "https://infisical.com"
+} as OAuthPasswordResetTemplateProps;

backend/src/services/smtp/emails/index.ts

@@ -7,6 +7,7 @@ export * from "./ExternalImportStartedTemplate";
 export * from "./ExternalImportSucceededTemplate";
 export * from "./IntegrationSyncFailedTemplate";
 export * from "./NewDeviceLoginTemplate";
+export * from "./OAuthPasswordResetTemplate";
 export * from "./OrgAdminBreakglassAccessTemplate";
 export * from "./OrgAdminProjectGrantAccessTemplate";
 export * from "./OrganizationAssignmentTemplate";

backend/src/services/smtp/smtp-service.ts

@@ -16,6 +16,7 @@ import {
   ExternalImportSucceededTemplate,
   IntegrationSyncFailedTemplate,
   NewDeviceLoginTemplate,
+  OAuthPasswordResetTemplate,
   OrgAdminBreakglassAccessTemplate,
   OrgAdminProjectGrantAccessTemplate,
   OrganizationAssignmentTemplate,
@@ -63,6 +64,7 @@ export enum SmtpTemplates {
   NewDeviceJoin = "newDevice",
   OrgInvite = "organizationInvitation",
   OrgAssignment = "organizationAssignment",
+  OAuthPasswordReset = "oAuthPasswordReset",
   ResetPassword = "passwordReset",
   SetupPassword = "passwordSetup",
   SecretLeakIncident = "secretLeakIncident",
@@ -121,6 +123,7 @@ const EmailTemplateMap: Record<SmtpTemplates, React.FC<any>> = {
   [SmtpTemplates.OrgAdminProjectDirectAccess]: OrgAdminProjectGrantAccessTemplate,
   [SmtpTemplates.ProjectAccessRequest]: ProjectAccessRequestTemplate,
   [SmtpTemplates.SecretApprovalRequestNeedsReview]: SecretApprovalRequestNeedsReviewTemplate,
+  [SmtpTemplates.OAuthPasswordReset]: OAuthPasswordResetTemplate,
   [SmtpTemplates.ResetPassword]: PasswordResetTemplate,
   [SmtpTemplates.SetupPassword]: PasswordSetupTemplate,
   [SmtpTemplates.PkiExpirationAlert]: PkiExpirationAlertTemplate,

backend/src/services/totp/totp-service.ts

@@ -131,15 +131,20 @@ export const totpServiceFactory = ({ totpConfigDAL, kmsService, userDAL }: TTotp
       secret
     });
 
-    if (isValid) {
-      await totpConfigDAL.updateById(totpConfig.id, {
-        isVerified: true
-      });
-    } else {
+    if (!isValid) {
       throw new BadRequestError({
         message: "Invalid TOTP token"
       });
     }
+
+    await totpConfigDAL.updateById(totpConfig.id, {
+      isVerified: true
+    });
+
+    const recoveryCodes = decryptWithRoot(totpConfig.encryptedRecoveryCodes).toString().split(",");
+    return {
+      recoveryCodes
+    };
   };
 
   const verifyUserTotp = async ({ userId, totp }: TVerifyUserTotpDTO) => {

backend/src/services/upgrade-path/github-client.ts

@@ -0,0 +1,242 @@
+/* eslint-disable no-await-in-loop */
+import RE2 from "re2";
+
+import { getConfig } from "@app/lib/config/env";
+
+import { FormattedRelease, GitHubApiError, GitHubRelease } from "./types";
+
+interface GitHubClientConfig {
+  token?: string;
+  timeout: number;
+  maxRetries: number;
+  retryDelay: number;
+  maxPagesPerRequest: number;
+  perPage: number;
+}
+
+interface RateLimitInfo {
+  remaining: number;
+  reset: Date;
+  used: number;
+  limit: number;
+}
+
+const getDefaultConfig = (): GitHubClientConfig => ({
+  token: getConfig().GITHUB_API_TOKEN,
+  timeout: 30000,
+  maxRetries: 3,
+  retryDelay: 1000,
+  maxPagesPerRequest: 10,
+  perPage: 100
+});
+
+const getHeaders = (token?: string): Record<string, string> => {
+  const headers: Record<string, string> = {
+    Accept: "application/vnd.github.v3+json",
+    "User-Agent": "Infisical-Upgrade-Path-Tool/1.0",
+    "X-GitHub-Api-Version": "2022-11-28"
+  };
+
+  if (token) {
+    headers.Authorization = `token ${token}`;
+  }
+
+  return headers;
+};
+
+const delay = (ms: number): Promise<void> => {
+  return new Promise((resolve) => {
+    setTimeout(resolve, ms);
+  });
+};
+
+const isMainInfisicalRelease = (tagName: string): boolean => {
+  if (
+    tagName.startsWith("infisical-cli/") ||
+    tagName.startsWith("infisical-k8-operator/") ||
+    tagName.startsWith("infisical-k8s-operator/")
+  ) {
+    return false;
+  }
+
+  const patterns = [
+    new RE2(/^v\d+\.\d+\.\d+/),
+    new RE2(/^\d+\.\d+\.\d+/),
+    new RE2(/^infisical\/v?\d+\.\d+\.\d+/),
+    new RE2(/^infisical\/v?\d+\.\d+\.\d+[-\w]*/)
+  ];
+
+  return patterns.some((pattern) => pattern.test(tagName));
+};
+
+const normalizeVersion = (tagName: string): string => {
+  const versionMatch = tagName.match(new RE2(/(\d+\.\d+\.\d+(?:\.\d+)?)/));
+  if (versionMatch) {
+    return `v${versionMatch[1]}`;
+  }
+
+  if (tagName.startsWith("infisical/")) {
+    const withoutPrefix = tagName.replace(new RE2(/^infisical\//), "");
+    return withoutPrefix.replace(new RE2(/-[a-zA-Z]+$/), "");
+  }
+  return tagName.replace(new RE2(/-[a-zA-Z]+$/), "");
+};
+
+const compareVersions = (v1: string, v2: string): number => {
+  const normalize = (v: string) => {
+    const versionMatch = v.match(new RE2(/(\d+\.\d+\.\d+(?:\.\d+)?)/));
+    if (versionMatch) {
+      return versionMatch[1];
+    }
+    if (v.startsWith("infisical/")) {
+      return v.replace(new RE2(/^infisical\/v?/), "").replace(new RE2(/-[a-zA-Z]+$/), "");
+    }
+    return v.replace(new RE2(/^v/), "").replace(new RE2(/-[a-zA-Z]+$/), "");
+  };
+
+  const clean1 = normalize(v1);
+  const clean2 = normalize(v2);
+
+  const parts1 = clean1.split(".").map(Number);
+  const parts2 = clean2.split(".").map(Number);
+
+  const maxLength = Math.max(parts1.length, parts2.length);
+  while (parts1.length < maxLength) parts1.push(0);
+  while (parts2.length < maxLength) parts2.push(0);
+
+  for (let i = 0; i < maxLength; i += 1) {
+    if (parts1[i] > parts2[i]) return 1;
+    if (parts1[i] < parts2[i]) return -1;
+  }
+  return 0;
+};
+
+const isVersionAtLeastMinimum = (tagName: string, minimumVersion = "0.147.0"): boolean => {
+  return compareVersions(tagName, minimumVersion) >= 0;
+};
+
+const makeRequest = async <T>(
+  url: string,
+  config: GitHubClientConfig,
+  retryCount = 0
+): Promise<{ data: T; rateLimit: RateLimitInfo }> => {
+  const controller = new AbortController();
+  const timeout = setTimeout(() => controller.abort(), config.timeout);
+
+  try {
+    const response = await fetch(url, {
+      headers: getHeaders(config.token),
+      signal: controller.signal
+    });
+
+    clearTimeout(timeout);
+
+    const rateLimit: RateLimitInfo = {
+      remaining: parseInt(response.headers.get("X-RateLimit-Remaining") || "0", 10),
+      reset: new Date(parseInt(response.headers.get("X-RateLimit-Reset") || "0", 10) * 1000),
+      used: parseInt(response.headers.get("X-RateLimit-Used") || "0", 10),
+      limit: parseInt(response.headers.get("X-RateLimit-Limit") || "5000", 10)
+    };
+
+    if (!response.ok) {
+      const error: GitHubApiError = new Error(`GitHub API error: ${response.status}`);
+      error.status = response.status;
+      error.headers = response.headers;
+
+      if (response.status === 403) {
+        const resetTime = rateLimit.reset.toISOString();
+        error.message = `GitHub API rate limit exceeded. Remaining: ${rateLimit.remaining}, Reset at: ${resetTime}. ${
+          !config.token ? "Consider setting GITHUB_TOKEN environment variable." : ""
+        }`;
+      }
+
+      if (retryCount < config.maxRetries && (response.status >= 500 || response.status === 403)) {
+        await delay(config.retryDelay * 2 ** retryCount);
+        return await makeRequest<T>(url, config, retryCount + 1);
+      }
+
+      throw error;
+    }
+
+    const data = (await response.json()) as T;
+    return { data, rateLimit };
+  } catch (error) {
+    clearTimeout(timeout);
+
+    if (error instanceof Error && error.name === "AbortError") {
+      if (retryCount < config.maxRetries) {
+        await delay(config.retryDelay * 2 ** retryCount);
+        return await makeRequest<T>(url, config, retryCount + 1);
+      }
+      throw new Error(`Request timeout after ${config.timeout}ms`);
+    }
+
+    if (retryCount < config.maxRetries && !(error as GitHubApiError).status) {
+      await delay(config.retryDelay * 2 ** retryCount);
+      return await makeRequest<T>(url, config, retryCount + 1);
+    }
+
+    throw error;
+  }
+};
+
+export const fetchReleases = async (includePrerelease = false): Promise<FormattedRelease[]> => {
+  const config = getDefaultConfig();
+  const allReleases: GitHubRelease[] = [];
+  let page = 1;
+  let hasMorePages = true;
+  let reachedMinimumVersion = false;
+
+  const maxConcurrentRequests = Math.min(3, config.maxPagesPerRequest);
+
+  while (hasMorePages && page <= config.maxPagesPerRequest && !reachedMinimumVersion) {
+    const requests: Promise<{ data: GitHubRelease[]; rateLimit: RateLimitInfo }>[] = [];
+
+    for (let i = 0; i < maxConcurrentRequests && page <= config.maxPagesPerRequest; i += 1, page += 1) {
+      const url = `https://api.github.com/repos/Infisical/infisical/releases?page=${page}&per_page=${config.perPage}`;
+      requests.push(makeRequest<GitHubRelease[]>(url, config));
+    }
+
+    const results = await Promise.allSettled(requests);
+    let hasData = false;
+
+    for (const result of results) {
+      if (result.status === "fulfilled") {
+        const { data } = result.value;
+        if (data.length > 0) {
+          for (const release of data) {
+            if (!release.draft && isMainInfisicalRelease(release.tag_name)) {
+              if (isVersionAtLeastMinimum(release.tag_name)) {
+                allReleases.push(release);
+              } else {
+                reachedMinimumVersion = true;
+                break;
+              }
+            }
+          }
+          hasData = true;
+        }
+      }
+    }
+
+    if (!hasData || results.every((r) => r.status === "fulfilled" && r.value.data.length < config.perPage)) {
+      hasMorePages = false;
+    }
+  }
+
+  const formattedReleases = allReleases
+    .map(
+      (release): FormattedRelease => ({
+        tagName: release.tag_name,
+        normalizedTagName: normalizeVersion(release.tag_name),
+        name: release.name,
+        body: release.body,
+        publishedAt: release.published_at,
+        prerelease: release.prerelease,
+        draft: release.draft
+      })
+    )
+    .sort((a, b) => new Date(b.publishedAt).getTime() - new Date(a.publishedAt).getTime());
+
+  return formattedReleases.filter((release) => includePrerelease || !release.prerelease);
+};

backend/src/services/upgrade-path/index.ts

@@ -0,0 +1,2 @@
+export type { TUpgradePathService, TUpgradePathServiceFactory } from "./upgrade-path-service";
+export { upgradePathServiceFactory } from "./upgrade-path-service";

backend/src/services/upgrade-path/types.ts

@@ -0,0 +1,66 @@
+export interface GitHubRelease {
+  tag_name: string;
+  name: string;
+  body: string;
+  published_at: string;
+  prerelease: boolean;
+  draft: boolean;
+}
+
+export interface FormattedRelease {
+  tagName: string;
+  normalizedTagName: string;
+  name: string;
+  body: string;
+  publishedAt: string;
+  prerelease: boolean;
+  draft: boolean;
+}
+
+export interface BreakingChange {
+  title: string;
+  description: string;
+  action: string;
+}
+
+export interface VersionConfig {
+  breaking_changes?: BreakingChange[];
+  db_schema_changes?: string;
+  notes?: string;
+}
+
+export interface UpgradePathConfig {
+  versions?: Record<string, VersionConfig>;
+}
+
+export interface UpgradePathResult {
+  path: Array<{
+    version: string;
+    name: string;
+    publishedAt: string;
+    prerelease: boolean;
+  }>;
+  breakingChanges: Array<{
+    version: string;
+    changes: BreakingChange[];
+  }>;
+  features: Array<{
+    version: string;
+    name: string;
+    body: string;
+    publishedAt: string;
+  }>;
+  hasDbMigration: boolean;
+  config: Record<string, unknown>;
+}
+
+export interface GitHubApiError extends Error {
+  status?: number;
+  headers?: Headers;
+}
+
+export interface CacheEntry<T> {
+  data: T;
+  timestamp: number;
+  ttl: number;
+}

backend/src/services/upgrade-path/upgrade-path-schemas.ts

@@ -0,0 +1,24 @@
+import RE2 from "re2";
+import { z } from "zod";
+
+export const versionSchema = z
+  .string()
+  .min(1)
+  .max(50)
+  .regex(new RE2(/^[a-zA-Z0-9._/-]+$/), "Invalid version format");
+
+export const breakingChangeSchema = z.object({
+  title: z.string().min(1).max(200),
+  description: z.string().min(1).max(1000),
+  action: z.string().min(1).max(500)
+});
+
+export const versionConfigSchema = z.object({
+  breaking_changes: z.array(breakingChangeSchema).optional(),
+  db_schema_changes: z.string().max(1000).optional(),
+  notes: z.string().max(2000).optional()
+});
+
+export const upgradePathConfigSchema = z.object({
+  versions: z.record(versionSchema, versionConfigSchema).optional().nullable()
+});

backend/src/services/upgrade-path/upgrade-path-service.ts

@@ -0,0 +1,259 @@
+import { readFile } from "fs/promises";
+import * as yaml from "js-yaml";
+import * as path from "path";
+import RE2 from "re2";
+import { z } from "zod";
+
+import { TKeyStoreFactory } from "@app/keystore/keystore";
+import { logger } from "@app/lib/logger";
+
+import { fetchReleases } from "./github-client";
+import { BreakingChange, FormattedRelease, UpgradePathConfig, UpgradePathResult, VersionConfig } from "./types";
+import { versionConfigSchema, versionSchema } from "./upgrade-path-schemas";
+
+export type TUpgradePathServiceFactory = {
+  keyStore: TKeyStoreFactory;
+};
+export type TUpgradePathService = ReturnType<typeof upgradePathServiceFactory>;
+
+interface CalculateUpgradePathParams {
+  fromVersion: string;
+  toVersion: string;
+}
+
+export const upgradePathServiceFactory = ({ keyStore }: TUpgradePathServiceFactory) => {
+  const sanitizeCacheKey = (key: string): string => {
+    return key.replace(new RE2(/[^a-zA-Z0-9\-:._]/g), "_");
+  };
+  const getGitHubReleases = async (): Promise<FormattedRelease[]> => {
+    const cacheKey = "upgrade-path:releases";
+
+    try {
+      const cached = await keyStore.getItem(cacheKey);
+      if (cached) {
+        const cachedReleases = JSON.parse(cached) as FormattedRelease[];
+        if (cachedReleases.length > 0) {
+          return cachedReleases;
+        }
+      }
+    } catch (error) {
+      logger.error(error, "Failed to retrieve releases from cache");
+    }
+
+    try {
+      const releases = await fetchReleases(false);
+      const filteredReleases = releases.filter((v) => !v.tagName.includes("nightly"));
+
+      await keyStore.setItemWithExpiry(cacheKey, 24 * 60 * 60, JSON.stringify(filteredReleases));
+      return filteredReleases;
+    } catch (error) {
+      throw new Error(`GitHub releases unavailable: ${error instanceof Error ? error.message : "Unknown error"}`);
+    }
+  };
+
+  const getUpgradePathConfig = async (): Promise<Record<string, z.infer<typeof versionConfigSchema>>> => {
+    const cacheKey = "upgrade-path:config";
+
+    try {
+      const cached = await keyStore.getItem(cacheKey);
+      if (cached) return JSON.parse(cached) as Record<string, VersionConfig>;
+    } catch (error) {
+      logger.error(error, "Failed to retrieve config from cache");
+    }
+
+    try {
+      const yamlPath = path.join(__dirname, "..", "..", "..", "upgrade-path.yaml");
+      const resolvedPath = path.resolve(yamlPath);
+      const expectedBaseDir = path.resolve(__dirname, "..", "..", "..");
+      if (!resolvedPath.startsWith(expectedBaseDir)) {
+        throw new Error("Invalid configuration file path");
+      }
+
+      const yamlContent = await readFile(yamlPath, "utf8");
+
+      if (yamlContent.length > 1024 * 1024) {
+        throw new Error("Config file too large");
+      }
+
+      const config = yaml.load(yamlContent, { schema: yaml.FAILSAFE_SCHEMA }) as UpgradePathConfig;
+      const versionConfig = config?.versions || {};
+
+      await keyStore.setItemWithExpiry(cacheKey, 24 * 60 * 60, JSON.stringify(versionConfig));
+      return versionConfig;
+    } catch (error) {
+      if (error instanceof Error && "code" in error && error.code === "ENOENT") {
+        const empty = {};
+        await keyStore.setItemWithExpiry(cacheKey, 24 * 60 * 60, JSON.stringify(empty));
+        return empty;
+      }
+      throw new Error(`Config load failed: ${error instanceof Error ? error.message : "Unknown error"}`);
+    }
+  };
+
+  const normalizeVersion = (version: string): string => {
+    const versionRegex = new RE2(/(\d+\.\d+\.\d+(?:\.\d+)?)/);
+    const versionMatch = version.match(versionRegex);
+    if (versionMatch) {
+      return versionMatch[1];
+    }
+
+    if (version.startsWith("infisical/")) {
+      return version.replace(new RE2(/^infisical\/v?/), "").replace(new RE2(/-[a-zA-Z]+$/), "");
+    }
+    return version.replace(new RE2(/^v/), "").replace(new RE2(/-[a-zA-Z]+$/), "");
+  };
+
+  const validateParams = (params: CalculateUpgradePathParams) => {
+    const { fromVersion, toVersion } = params;
+
+    versionSchema.parse(fromVersion);
+    versionSchema.parse(toVersion);
+
+    if (fromVersion === toVersion) {
+      throw new Error("Versions cannot be identical");
+    }
+
+    if (fromVersion.includes("nightly") || toVersion.includes("nightly")) {
+      throw new Error("Nightly releases are not supported for upgrade path calculation");
+    }
+
+    return { fromVersion, toVersion };
+  };
+
+  const calculateUpgradePath = async (params: CalculateUpgradePathParams): Promise<UpgradePathResult> => {
+    const { fromVersion, toVersion } = validateParams(params);
+    const cacheKey = sanitizeCacheKey(`upgrade-path:${fromVersion}:${toVersion}`);
+
+    try {
+      const cached = await keyStore.getItem(cacheKey);
+      if (cached) return JSON.parse(cached) as UpgradePathResult;
+    } catch (error) {
+      logger.error(error, "Failed to retrieve upgrade path from cache");
+    }
+
+    const [releases, config] = await Promise.all([getGitHubReleases(), getUpgradePathConfig()]);
+
+    const cleanFrom = normalizeVersion(fromVersion);
+    const cleanTo = normalizeVersion(toVersion);
+
+    const compareVersions = (v1: string, v2: string): number => {
+      const normalize = (v: string) => normalizeVersion(v);
+      const clean1 = normalize(v1);
+      const clean2 = normalize(v2);
+
+      const parts1 = clean1.split(".").map(Number);
+      const parts2 = clean2.split(".").map(Number);
+
+      const maxLength = Math.max(parts1.length, parts2.length);
+      while (parts1.length < maxLength) parts1.push(0);
+      while (parts2.length < maxLength) parts2.push(0);
+
+      for (let i = 0; i < maxLength; i += 1) {
+        if (parts1[i] > parts2[i]) return 1;
+        if (parts1[i] < parts2[i]) return -1;
+      }
+      return 0;
+    };
+
+    if (compareVersions(cleanFrom, cleanTo) >= 0) {
+      throw new Error("fromVersion must be older than toVersion");
+    }
+
+    const fromIdx = releases.findIndex((r) => normalizeVersion(r.normalizedTagName) === cleanFrom);
+    const toIdx = releases.findIndex((r) => normalizeVersion(r.normalizedTagName) === cleanTo);
+
+    let upgradePath: FormattedRelease[] = [];
+    const filteredPath: FormattedRelease[] = [];
+
+    if (fromIdx !== -1 && toIdx !== -1) {
+      if (fromIdx <= toIdx) throw new Error("Invalid version order");
+      upgradePath = releases.slice(toIdx, fromIdx + 1).reverse();
+      const [first, last] = [upgradePath[0], upgradePath[upgradePath.length - 1]];
+
+      filteredPath.push(first);
+      if (last !== first) filteredPath.push(last);
+    }
+
+    const breakingChanges: Array<{ version: string; changes: BreakingChange[] }> = [];
+    const features: Array<{ version: string; name: string; body: string; publishedAt: string }> = [];
+    let hasDbMigration = false;
+
+    const isVersionInRange = (version: string, fromVer: string, toVer: string): boolean => {
+      const versionComp = compareVersions(version, fromVer);
+      const toVersionComp = compareVersions(version, toVer);
+      return versionComp > 0 && toVersionComp < 0;
+    };
+
+    Object.keys(config).forEach((configVersion) => {
+      const versionConfig = config[configVersion];
+      if (versionConfig?.breaking_changes?.length) {
+        if (isVersionInRange(configVersion, cleanFrom, cleanTo)) {
+          breakingChanges.push({
+            version: configVersion,
+            changes: versionConfig.breaking_changes
+          });
+        }
+      }
+    });
+    for (let i = 0; i < upgradePath.length; i += 1) {
+      const version = upgradePath[i];
+      const isFromVersion = normalizeVersion(version.normalizedTagName) === cleanFrom;
+
+      if (!isFromVersion) {
+        const versionNumber = normalizeVersion(version.tagName);
+        const possibleKeys = [
+          version.tagName,
+          version.normalizedTagName,
+          versionNumber,
+          `v${versionNumber}`,
+          version.tagName.replace(new RE2(/^infisical\//), ""),
+          version.tagName.replace(new RE2(/^infisical\/v?/), "").replace(new RE2(/-[a-zA-Z]+$/), "")
+        ];
+
+        for (const key of possibleKeys) {
+          const versionConfig = config[key];
+          if (
+            versionConfig?.db_schema_changes &&
+            typeof versionConfig.db_schema_changes === "string" &&
+            versionConfig.db_schema_changes.trim()
+          ) {
+            hasDbMigration = true;
+            break;
+          }
+        }
+      }
+
+      // Collect release notes and features
+      if (version.body) {
+        features.push({
+          version: version.tagName,
+          name: version.name,
+          body: version.body,
+          publishedAt: version.publishedAt
+        });
+      }
+    }
+
+    const result: UpgradePathResult = {
+      path: filteredPath.map((r) => ({
+        version: r.tagName,
+        name: r.name,
+        publishedAt: r.publishedAt,
+        prerelease: r.prerelease
+      })),
+      breakingChanges,
+      features,
+      hasDbMigration,
+      config
+    };
+
+    await keyStore.setItemWithExpiry(cacheKey, 60 * 60, JSON.stringify(result));
+    return result;
+  };
+
+  return {
+    getGitHubReleases,
+    getUpgradePathConfig,
+    calculateUpgradePath: (fromVersion: string, toVersion: string) => calculateUpgradePath({ fromVersion, toVersion })
+  };
+};

backend/src/services/webhook/webhook-fns.ts

@@ -94,6 +94,7 @@ export const getWebhookPayload = (event: TWebhookPayloads) => {
           event: event.type,
           project: {
             workspaceId: projectId,
+            projectId,
             projectName,
             environment,
             secretPath
@@ -147,6 +148,7 @@ export const getWebhookPayload = (event: TWebhookPayloads) => {
         event: event.type,
         project: {
           workspaceId: projectId,
+          projectId,
           projectName,
           environment,
           secretPath,