diff --git a/packages/server/modules/backgroundjobs/repositories/backgroundjobs.ts b/packages/server/modules/backgroundjobs/repositories/backgroundjobs.ts
index 2243f2ea2..1d934f2f9 100644
--- a/packages/server/modules/backgroundjobs/repositories/backgroundjobs.ts
+++ b/packages/server/modules/backgroundjobs/repositories/backgroundjobs.ts
@@ -65,20 +65,37 @@ export const failBackgroundJobsWhichExceedMaximumAttemptsOrNoRemainingComputeBud
         .backgroundJobs(db)
         .where(BackgroundJobs.withoutTablePrefix.col.originServerUrl, originServerUrl)
         .andWhere(BackgroundJobs.withoutTablePrefix.col.jobType, jobType)
-        .whereIn(BackgroundJobs.withoutTablePrefix.col.status, [
-          BackgroundJobStatus.Queued,
-          BackgroundJobStatus.Processing
-        ])
         .andWhere(function () {
-          this.where(
-            BackgroundJobs.withoutTablePrefix.col.attempt,
-            '>', // greater than because processing jobs may currently equal maxAttempt and still be running
-            db.raw('"maxAttempt"') // camelCase requires the column name to be wrapped in double quotes
-          ).orWhere(
-            BackgroundJobs.withoutTablePrefix.col.remainingComputeBudgetSeconds,
-            '<=',
-            0
-          )
+          this.where(function () {
+            this.where(
+              BackgroundJobs.withoutTablePrefix.col.status,
+              BackgroundJobStatus.Processing
+            ).andWhere(
+              BackgroundJobs.withoutTablePrefix.col.attempt,
+              '>', // greater than because processing jobs may currently equal maxAttempt and still be running
+              db.raw('"maxAttempt"') // camelCase requires the column name to be wrapped in double quotes
+            )
+          })
+            .orWhere(function () {
+              this.where(
+                BackgroundJobs.withoutTablePrefix.col.status,
+                BackgroundJobStatus.Queued
+              ).andWhere(
+                BackgroundJobs.withoutTablePrefix.col.attempt,
+                '>=', // greater or equal than because queued jobs cannot be picked up by a worker when they reach maxAttempt
+                db.raw('"maxAttempt"') // camelCase requires the column name to be wrapped in double quotes
+              )
+            })
+            .orWhere(function () {
+              this.whereIn(BackgroundJobs.withoutTablePrefix.col.status, [
+                BackgroundJobStatus.Queued,
+                BackgroundJobStatus.Processing
+              ]).where(
+                BackgroundJobs.withoutTablePrefix.col.remainingComputeBudgetSeconds,
+                '<=',
+                0
+              )
+            })
         })
         .update({
           [BackgroundJobs.withoutTablePrefix.col.status]: BackgroundJobStatus.Failed
diff --git a/packages/server/modules/backgroundjobs/tests/integration/repositories.spec.ts b/packages/server/modules/backgroundjobs/tests/integration/repositories.spec.ts
index d6f37c40c..82cf429ed 100644
--- a/packages/server/modules/backgroundjobs/tests/integration/repositories.spec.ts
+++ b/packages/server/modules/backgroundjobs/tests/integration/repositories.spec.ts
@@ -174,10 +174,10 @@ describe('Background Jobs repositories @backgroundjobs', () => {
   })
 
   describe('failQueuedBackgroundJobsWhichExceedMaximumAttemptsOrNoRemainingComputeBudgetFactory', () => {
-    it('should fail queued background jobs that exceed maximum attempts', async () => {
+    it('should fail queued background jobs that meet or exceed maximum attempts', async () => {
       const job = createTestJob({
         status: BackgroundJobStatus.Queued,
-        attempt: 3,
+        attempt: 2,
         maxAttempt: 2
       })
       await storeBackgroundJob({ job })
diff --git a/packages/server/modules/fileuploads/tests/integration/tasks.spec.ts b/packages/server/modules/fileuploads/tests/integration/tasks.spec.ts
index a45864e49..189330a82 100644
--- a/packages/server/modules/fileuploads/tests/integration/tasks.spec.ts
+++ b/packages/server/modules/fileuploads/tests/integration/tasks.spec.ts
@@ -179,7 +179,7 @@ describe('File import garbage collection @fileuploads integration', () => {
           testData: identifiableData,
           blobId: fileTwo.fileId
         }),
-        attempt: 4,
+        attempt: 3,
         maxAttempt: 3
       })
       await saveUploadFile(fileOne)