diff --git a/backend/src/ee/services/audit-log/audit-log-types.ts b/backend/src/ee/services/audit-log/audit-log-types.ts
index 91464bc0b..a31200a1b 100644
--- a/backend/src/ee/services/audit-log/audit-log-types.ts
+++ b/backend/src/ee/services/audit-log/audit-log-types.ts
@@ -234,6 +234,7 @@ export enum EventType {
   GET_PROJECT_KMS_BACKUP = "get-project-kms-backup",
   LOAD_PROJECT_KMS_BACKUP = "load-project-kms-backup",
   ORG_ADMIN_ACCESS_PROJECT = "org-admin-accessed-project",
+  ORG_ADMIN_BYPASS_SSO = "org-admin-bypassed-sso",
   CREATE_CERTIFICATE_TEMPLATE = "create-certificate-template",
   UPDATE_CERTIFICATE_TEMPLATE = "update-certificate-template",
   DELETE_CERTIFICATE_TEMPLATE = "delete-certificate-template",
@@ -1907,6 +1908,11 @@ interface OrgAdminAccessProjectEvent {
   }; // no metadata yet
 }
 
+interface OrgAdminBypassSSOEvent {
+  type: EventType.ORG_ADMIN_BYPASS_SSO;
+  metadata: Record<string, string>; // no metadata yet
+}
+
 interface CreateCertificateTemplateEstConfig {
   type: EventType.CREATE_CERTIFICATE_TEMPLATE_EST_CONFIG;
   metadata: {
@@ -2656,6 +2662,7 @@ export type Event =
   | GetProjectKmsBackupEvent
   | LoadProjectKmsBackupEvent
   | OrgAdminAccessProjectEvent
+  | OrgAdminBypassSSOEvent
   | CreateCertificateTemplate
   | UpdateCertificateTemplate
   | GetCertificateTemplate
diff --git a/backend/src/server/routes/index.ts b/backend/src/server/routes/index.ts
index 54c6b96b2..2c1b768fb 100644
--- a/backend/src/server/routes/index.ts
+++ b/backend/src/server/routes/index.ts
@@ -596,7 +596,14 @@ export const registerRoutes = async (
     kmsService
   });
 
-  const loginService = authLoginServiceFactory({ userDAL, smtpService, tokenService, orgDAL, totpService });
+  const loginService = authLoginServiceFactory({
+    userDAL,
+    smtpService,
+    tokenService,
+    orgDAL,
+    totpService,
+    auditLogService
+  });
   const passwordService = authPaswordServiceFactory({
     tokenService,
     smtpService,
diff --git a/backend/src/services/auth/auth-login-service.ts b/backend/src/services/auth/auth-login-service.ts
index 0e0f999dd..e576d6768 100644
--- a/backend/src/services/auth/auth-login-service.ts
+++ b/backend/src/services/auth/auth-login-service.ts
@@ -3,6 +3,8 @@ import jwt from "jsonwebtoken";
 import { Knex } from "knex";
 
 import { OrgMembershipRole, TUsers, UserDeviceSchema } from "@app/db/schemas";
+import { TAuditLogServiceFactory } from "@app/ee/services/audit-log/audit-log-service";
+import { EventType } from "@app/ee/services/audit-log/audit-log-types";
 import { isAuthMethodSaml } from "@app/ee/services/permission/permission-fns";
 import { getConfig } from "@app/lib/config/env";
 import { request } from "@app/lib/config/request";
@@ -11,6 +13,7 @@ import { infisicalSymmetricEncypt } from "@app/lib/crypto/encryption";
 import { getUserPrivateKey } from "@app/lib/crypto/srp";
 import { BadRequestError, DatabaseError, ForbiddenRequestError, UnauthorizedError } from "@app/lib/errors";
 import { logger } from "@app/lib/logger";
+import { getUserAgentType } from "@app/server/plugins/audit-log";
 import { getServerCfg } from "@app/services/super-admin/super-admin-service";
 
 import { TAuthTokenServiceFactory } from "../auth-token/auth-token-service";
@@ -28,7 +31,15 @@ import {
   TOauthTokenExchangeDTO,
   TVerifyMfaTokenDTO
 } from "./auth-login-type";
-import { AuthMethod, AuthModeJwtTokenPayload, AuthModeMfaJwtTokenPayload, AuthTokenType, MfaMethod } from "./auth-type";
+import {
+  ActorType,
+  AuthMethod,
+  AuthModeJwtTokenPayload,
+  AuthModeMfaJwtTokenPayload,
+  AuthTokenType,
+  MfaMethod
+} from "./auth-type";
+import { removeTrailingSlash } from "@app/lib/fn";
 
 type TAuthLoginServiceFactoryDep = {
   userDAL: TUserDALFactory;
@@ -36,6 +47,7 @@ type TAuthLoginServiceFactoryDep = {
   tokenService: TAuthTokenServiceFactory;
   smtpService: TSmtpService;
   totpService: Pick<TTotpServiceFactory, "verifyUserTotp" | "verifyWithUserRecoveryCode">;
+  auditLogService: Pick<TAuditLogServiceFactory, "createAuditLog">;
 };
 
 export type TAuthLoginFactory = ReturnType<typeof authLoginServiceFactory>;
@@ -44,7 +56,8 @@ export const authLoginServiceFactory = ({
   tokenService,
   smtpService,
   orgDAL,
-  totpService
+  totpService,
+  auditLogService
 }: TAuthLoginServiceFactoryDep) => {
   /*
    * Private
@@ -412,6 +425,55 @@ export const authLoginServiceFactory = ({
       mfaMethod: decodedToken.mfaMethod
     });
 
+    // In the event of this being a break-glass request (non-saml / non-oidc, when either is enforced)
+    if (
+      selectedOrg.authEnforced &&
+      selectedOrg.bypassOrgAuthEnabled &&
+      !isAuthMethodSaml(decodedToken.authMethod) &&
+      decodedToken.authMethod !== AuthMethod.OIDC
+    ) {
+      await auditLogService.createAuditLog({
+        orgId: organizationId,
+        ipAddress,
+        userAgent,
+        userAgentType: getUserAgentType(userAgent),
+        actor: {
+          type: ActorType.USER,
+          metadata: {
+            email: user.email,
+            userId: user.id,
+            username: user.username
+          }
+        },
+        event: {
+          type: EventType.ORG_ADMIN_BYPASS_SSO,
+          metadata: {}
+        }
+      });
+
+      // Notify all admins via email (besides the actor)
+      const orgAdmins = await orgDAL.findOrgMembersByRole(organizationId, OrgMembershipRole.Admin);
+      const adminEmails = orgAdmins
+        .filter((admin) => admin.user.id !== user.id)
+        .map((admin) => admin.user.email)
+        .filter(Boolean) as string[];
+
+      if (adminEmails.length > 0) {
+        await smtpService.sendMail({
+          recipients: adminEmails,
+          subjectLine: "Security Alert: Admin SSO Bypass",
+          substitutions: {
+            email: user.email,
+            timestamp: new Date().toISOString(),
+            ip: ipAddress,
+            userAgent,
+            siteUrl: removeTrailingSlash(cfg.SITE_URL || "https://app.infisical.com")
+          },
+          template: SmtpTemplates.OrgAdminBreakglassAccess
+        });
+      }
+    }
+
     return {
       ...tokens,
       isMfaEnabled: false
diff --git a/backend/src/services/org/org-dal.ts b/backend/src/services/org/org-dal.ts
index 02bf58321..54b0e1b0f 100644
--- a/backend/src/services/org/org-dal.ts
+++ b/backend/src/services/org/org-dal.ts
@@ -2,6 +2,7 @@ import { Knex } from "knex";
 
 import { TDbClient } from "@app/db";
 import {
+  OrgMembershipRole,
   TableName,
   TOrganizations,
   TOrganizationsInsert,
@@ -216,9 +217,8 @@ export const orgDALFactory = (db: TDbClient) => {
 
   const findOrgMembersByUsername = async (orgId: string, usernames: string[], tx?: Knex) => {
     try {
-      const conn = tx || db;
+      const conn = tx || db.replicaNode();
       const members = await conn(TableName.OrgMembership)
-        // .replicaNode()(TableName.OrgMembership)
         .where(`${TableName.OrgMembership}.orgId`, orgId)
         .join(TableName.Users, `${TableName.OrgMembership}.userId`, `${TableName.Users}.id`)
         .leftJoin<TUserEncryptionKeys>(
@@ -251,6 +251,43 @@ export const orgDALFactory = (db: TDbClient) => {
     }
   };
 
+  const findOrgMembersByRole = async (orgId: string, role: OrgMembershipRole, tx?: Knex) => {
+    try {
+      const conn = tx || db.replicaNode();
+      const members = await conn(TableName.OrgMembership)
+        .where(`${TableName.OrgMembership}.orgId`, orgId)
+        .where(`${TableName.OrgMembership}.role`, role)
+        .join(TableName.Users, `${TableName.OrgMembership}.userId`, `${TableName.Users}.id`)
+        .leftJoin<TUserEncryptionKeys>(
+          TableName.UserEncryptionKey,
+          `${TableName.UserEncryptionKey}.userId`,
+          `${TableName.Users}.id`
+        )
+        .select(
+          conn.ref("id").withSchema(TableName.OrgMembership),
+          conn.ref("inviteEmail").withSchema(TableName.OrgMembership),
+          conn.ref("orgId").withSchema(TableName.OrgMembership),
+          conn.ref("role").withSchema(TableName.OrgMembership),
+          conn.ref("roleId").withSchema(TableName.OrgMembership),
+          conn.ref("status").withSchema(TableName.OrgMembership),
+          conn.ref("username").withSchema(TableName.Users),
+          conn.ref("email").withSchema(TableName.Users),
+          conn.ref("firstName").withSchema(TableName.Users),
+          conn.ref("lastName").withSchema(TableName.Users),
+          conn.ref("id").withSchema(TableName.Users).as("userId"),
+          conn.ref("publicKey").withSchema(TableName.UserEncryptionKey)
+        )
+        .where({ isGhost: false });
+
+      return members.map(({ username, email, firstName, lastName, userId, publicKey, ...data }) => ({
+        ...data,
+        user: { username, email, firstName, lastName, id: userId, publicKey }
+      }));
+    } catch (error) {
+      throw new DatabaseError({ error, name: "Find org members by role" });
+    }
+  };
+
   const findOrgGhostUser = async (orgId: string) => {
     try {
       const member = await db
@@ -472,6 +509,7 @@ export const orgDALFactory = (db: TDbClient) => {
     findAllOrgsByUserId,
     ghostUserExists,
     findOrgMembersByUsername,
+    findOrgMembersByRole,
     findOrgGhostUser,
     create,
     updateById,
diff --git a/backend/src/services/smtp/smtp-service.ts b/backend/src/services/smtp/smtp-service.ts
index 25f5f3949..550e1bb07 100644
--- a/backend/src/services/smtp/smtp-service.ts
+++ b/backend/src/services/smtp/smtp-service.ts
@@ -44,6 +44,7 @@ export enum SmtpTemplates {
   SecretRotationFailed = "secretRotationFailed.handlebars",
   ProjectAccessRequest = "projectAccess.handlebars",
   OrgAdminProjectDirectAccess = "orgAdminProjectGrantAccess.handlebars",
+  OrgAdminBreakglassAccess = "orgAdminBreakglassAccess.handlebars",
   ServiceTokenExpired = "serviceTokenExpired.handlebars"
 }
 
diff --git a/backend/src/services/smtp/templates/orgAdminBreakglassAccess.handlebars b/backend/src/services/smtp/templates/orgAdminBreakglassAccess.handlebars
new file mode 100644
index 000000000..cc97ff201
--- /dev/null
+++ b/backend/src/services/smtp/templates/orgAdminBreakglassAccess.handlebars
@@ -0,0 +1,20 @@
+<html>
+
+  <head>
+    <meta charset="utf-8" />
+    <meta http-equiv="x-ua-compatible" content="ie=edge" />
+    <title>Organization admin has bypassed SSO</title>
+  </head>
+
+  <body>
+    <h2>Infisical</h2>
+    <p>The organization admin {{email}} has bypassed enforced SSO login.</p>
+    <p><strong>Timestamp</strong>: {{timestamp}}</p>
+    <p><strong>IP address</strong>: {{ip}}</p>
+    <p><strong>User agent</strong>: {{userAgent}}</p>
+    <p>If you'd like to disable Admin SSO Bypass, please visit <a href="{{siteUrl}}/organization/settings">Organization Settings</a> > Security.</p>
+
+    {{emailFooter}}
+  </body>
+
+</html>
diff --git a/frontend/src/hooks/api/auditLogs/constants.tsx b/frontend/src/hooks/api/auditLogs/constants.tsx
index 159e840ec..229f822da 100644
--- a/frontend/src/hooks/api/auditLogs/constants.tsx
+++ b/frontend/src/hooks/api/auditLogs/constants.tsx
@@ -84,6 +84,7 @@ export const eventToNameMap: { [K in EventType]: string } = {
   [EventType.ADD_PKI_COLLECTION_ITEM]: "Add PKI collection item",
   [EventType.DELETE_PKI_COLLECTION_ITEM]: "Delete PKI collection item",
   [EventType.ORG_ADMIN_ACCESS_PROJECT]: "Org admin accessed project",
+  [EventType.ORG_ADMIN_BYPASS_SSO]: "Org admin bypassed SSO enforcement",
   [EventType.CREATE_CERTIFICATE_TEMPLATE]: "Create certificate template",
   [EventType.UPDATE_CERTIFICATE_TEMPLATE]: "Update certificate template",
   [EventType.DELETE_CERTIFICATE_TEMPLATE]: "Delete certificate template",
diff --git a/frontend/src/hooks/api/auditLogs/enums.tsx b/frontend/src/hooks/api/auditLogs/enums.tsx
index 15adb0272..d465fb820 100644
--- a/frontend/src/hooks/api/auditLogs/enums.tsx
+++ b/frontend/src/hooks/api/auditLogs/enums.tsx
@@ -90,6 +90,7 @@ export enum EventType {
   ADD_PKI_COLLECTION_ITEM = "add-pki-collection-item",
   DELETE_PKI_COLLECTION_ITEM = "delete-pki-collection-item",
   ORG_ADMIN_ACCESS_PROJECT = "org-admin-accessed-project",
+  ORG_ADMIN_BYPASS_SSO = "org-admin-bypassed-sso",
   CREATE_CERTIFICATE_TEMPLATE = "create-certificate-template",
   UPDATE_CERTIFICATE_TEMPLATE = "update-certificate-template",
   DELETE_CERTIFICATE_TEMPLATE = "delete-certificate-template",
diff --git a/frontend/src/hooks/api/auditLogs/types.tsx b/frontend/src/hooks/api/auditLogs/types.tsx
index a18974f2e..2524f84f4 100644
--- a/frontend/src/hooks/api/auditLogs/types.tsx
+++ b/frontend/src/hooks/api/auditLogs/types.tsx
@@ -718,6 +718,11 @@ interface OrgAdminAccessProjectEvent {
   }; // no metadata yet
 }
 
+interface OrgAdminBypassSSOEvent {
+  type: EventType.ORG_ADMIN_BYPASS_SSO;
+  metadata: Record<string, string>; // no metadata yet
+}
+
 interface CreateCertificateTemplate {
   type: EventType.CREATE_CERTIFICATE_TEMPLATE;
   metadata: {
@@ -885,6 +890,7 @@ export type Event =
   | AddPkiCollectionItem
   | DeletePkiCollectionItem
   | OrgAdminAccessProjectEvent
+  | OrgAdminBypassSSOEvent
   | CreateCertificateTemplate
   | UpdateCertificateTemplate
   | GetCertificateTemplate