From 19c07311664fd8f926dab526d4f900dcc4e4ac2b Mon Sep 17 00:00:00 2001
From: x032205 <x032205@gmail.com>
Date: Wed, 9 Jul 2025 19:54:35 -0400
Subject: [PATCH] Add jitter and increase window to 12 m

---
 .../20250602155451_fix-secret-versions.ts     |  2 +-
 .../org-membership/org-membership-dal.ts      |  6 +--
 backend/src/services/org/org-service.ts       | 41 ++++++++++++-------
 3 files changed, 31 insertions(+), 18 deletions(-)

diff --git a/backend/src/db/migrations/20250602155451_fix-secret-versions.ts b/backend/src/db/migrations/20250602155451_fix-secret-versions.ts
index ace1895de..0fb23e327 100644
--- a/backend/src/db/migrations/20250602155451_fix-secret-versions.ts
+++ b/backend/src/db/migrations/20250602155451_fix-secret-versions.ts
@@ -3,7 +3,7 @@ import { Knex } from "knex";
 
 import { chunkArray } from "@app/lib/fn";
 import { selectAllTableCols } from "@app/lib/knex";
-import { logger, initLogger } from "@app/lib/logger";
+import { initLogger, logger } from "@app/lib/logger";
 
 import { SecretType, TableName } from "../schemas";
 
diff --git a/backend/src/services/org-membership/org-membership-dal.ts b/backend/src/services/org-membership/org-membership-dal.ts
index ebf1700d0..ed4867025 100644
--- a/backend/src/services/org-membership/org-membership-dal.ts
+++ b/backend/src/services/org-membership/org-membership-dal.ts
@@ -108,16 +108,16 @@ export const orgMembershipDALFactory = (db: TDbClient) => {
       const now = new Date();
       const oneWeekAgo = new Date(now.getTime() - 7 * 24 * 60 * 60 * 1000);
       const oneMonthAgo = new Date(now.getTime() - 30 * 24 * 60 * 60 * 1000);
-      const threeMonthsAgo = new Date(now.getTime() - 90 * 24 * 60 * 60 * 1000);
+      const twelveMonthsAgo = new Date(now.getTime() - 360 * 24 * 60 * 60 * 1000);
 
       const memberships = await db
         .replicaNode()(TableName.OrgMembership)
         .where("status", "invited")
         .where((qb) => {
-          // lastInvitedAt is null AND createdAt is between 1 week and 3 months ago
+          // lastInvitedAt is null AND createdAt is between 1 week and 12 months ago
           void qb
             .whereNull(`${TableName.OrgMembership}.lastInvitedAt`)
-            .whereBetween(`${TableName.OrgMembership}.createdAt`, [threeMonthsAgo, oneWeekAgo]);
+            .whereBetween(`${TableName.OrgMembership}.createdAt`, [twelveMonthsAgo, oneWeekAgo]);
         })
         .orWhere((qb) => {
           // lastInvitedAt is older than 1 week ago AND createdAt is younger than 1 month ago
diff --git a/backend/src/services/org/org-service.ts b/backend/src/services/org/org-service.ts
index 5941eb013..8917a4fc1 100644
--- a/backend/src/services/org/org-service.ts
+++ b/backend/src/services/org/org-service.ts
@@ -36,6 +36,8 @@ import { getConfig } from "@app/lib/config/env";
 import { generateAsymmetricKeyPair } from "@app/lib/crypto";
 import { generateSymmetricKey, infisicalSymmetricDecrypt, infisicalSymmetricEncypt } from "@app/lib/crypto/encryption";
 import { generateUserSrpKeys } from "@app/lib/crypto/srp";
+import { applyJitter } from "@app/lib/dates";
+import { delay as delayMs } from "@app/lib/delay";
 import {
   BadRequestError,
   ForbiddenRequestError,
@@ -44,9 +46,10 @@ import {
   UnauthorizedError
 } from "@app/lib/errors";
 import { groupBy } from "@app/lib/fn";
+import { logger } from "@app/lib/logger";
 import { alphaNumericNanoId } from "@app/lib/nanoid";
 import { isDisposableEmail } from "@app/lib/validator";
-import { TQueueServiceFactory } from "@app/queue";
+import { QueueName, TQueueServiceFactory } from "@app/queue";
 import { getDefaultOrgMembershipRoleForUpdateOrg } from "@app/services/org/org-role-fns";
 import { TOrgMembershipDALFactory } from "@app/services/org-membership/org-membership-dal";
 import { TUserAliasDALFactory } from "@app/services/user-alias/user-alias-dal";
@@ -1438,6 +1441,8 @@ export const orgServiceFactory = ({
    * Re-send emails to users who haven't accepted an invite yet
    */
   const notifyInvitedUsers = async () => {
+    logger.info(`${QueueName.DailyResourceCleanUp}: notify invited users started`);
+
     const invitedUsers = await orgMembershipDAL.findRecentInvitedMemberships();
     const appCfg = getConfig();
 
@@ -1461,24 +1466,32 @@ export const orgServiceFactory = ({
         });
 
         if (invitedUser.inviteEmail) {
-          await smtpService.sendMail({
-            template: SmtpTemplates.OrgInvite,
-            subjectLine: `Reminder: You have been invited to ${org.name} on Infisical`,
-            recipients: [invitedUser.inviteEmail],
-            substitutions: {
-              organizationName: org.name,
-              email: invitedUser.inviteEmail,
-              organizationId: org.id.toString(),
-              token,
-              callback_url: `${appCfg.SITE_URL}/signupinvite`
-            }
-          });
-          notifiedUsers.push(invitedUser.id);
+          await delayMs(Math.max(0, applyJitter(0, 2000)));
+
+          try {
+            await smtpService.sendMail({
+              template: SmtpTemplates.OrgInvite,
+              subjectLine: `Reminder: You have been invited to ${org.name} on Infisical`,
+              recipients: [invitedUser.inviteEmail],
+              substitutions: {
+                organizationName: org.name,
+                email: invitedUser.inviteEmail,
+                organizationId: org.id.toString(),
+                token,
+                callback_url: `${appCfg.SITE_URL}/signupinvite`
+              }
+            });
+            notifiedUsers.push(invitedUser.id);
+          } catch (err) {
+            logger.error(err, `${QueueName.DailyResourceCleanUp}: notify invited users failed to send email`);
+          }
         }
       })
     );
 
     await orgMembershipDAL.updateLastInvitedAtByIds(notifiedUsers);
+
+    logger.info(`${QueueName.DailyResourceCleanUp}: notify invited users completed`);
   };
 
   return {