diff --git a/src-ui/src/app/components/admin/tasks/tasks.component.html b/src-ui/src/app/components/admin/tasks/tasks.component.html
index d20d9045e..0026d8575 100644
--- a/src-ui/src/app/components/admin/tasks/tasks.component.html
+++ b/src-ui/src/app/components/admin/tasks/tasks.component.html
@@ -113,9 +113,7 @@
           <td scope="row">
             <div class="btn-group" role="group">
               @if (task.status === PaperlessTaskStatus.Failed) {
-                <button class="btn btn-sm btn-outline-primary" (click)="retryTask(task); $event.stopPropagation();" *pngxIfPermissions="{ action: PermissionAction.Change, type: PermissionType.PaperlessTask }">
-                  <i-bs name="arrow-repeat"></i-bs>&nbsp;<ng-container i18n>Retry</ng-container>
-                </button>
+                <ng-container *ngTemplateOutlet="retryDropdown; context: { task: task }"></ng-container>
               }
               <button class="btn btn-sm btn-outline-secondary" (click)="dismissTask(task); $event.stopPropagation();" *pngxIfPermissions="{ action: PermissionAction.Change, type: PermissionType.PaperlessTask }">
                 <i-bs name="check" class="me-1"></i-bs><ng-container i18n>Dismiss</ng-container>
@@ -189,3 +187,25 @@
   </li>
 </ul>
 <div [ngbNavOutlet]="nav"></div>
+
+<ng-template #retryDropdown let-task="task">
+  <div ngbDropdown>
+    <button class="btn btn-sm btn-outline-primary" (click)="$event.stopImmediatePropagation()" ngbDropdownToggle>
+      <i-bs name="arrow-repeat"></i-bs>&nbsp;<ng-container i18n>Retry</ng-container>
+    </button>
+    <div ngbDropdownMenu class="shadow retry-dropdown">
+      <div class="p-2">
+        <ul class="list-group list-group-flush">
+            <li class="list-group-item small" i18n>
+              <pngx-input-check [(ngModel)]="retryClean" i18n-title title="Attempt to clean pdf"></pngx-input-check>
+            </li>
+        </ul>
+        <div class="d-flex justify-content-end">
+          <button class="btn btn-sm btn-outline-primary" (click)="retryTask(task); $event.stopPropagation();">
+            <ng-container i18n>Proceed</ng-container>
+          </button>
+        </div>
+      </div>
+    </div>
+  </div>
+</ng-template>
diff --git a/src-ui/src/app/components/admin/tasks/tasks.component.scss b/src-ui/src/app/components/admin/tasks/tasks.component.scss
index 325fd2c02..8387597f6 100644
--- a/src-ui/src/app/components/admin/tasks/tasks.component.scss
+++ b/src-ui/src/app/components/admin/tasks/tasks.component.scss
@@ -37,3 +37,7 @@ pre {
 .z-10 {
     z-index: 10;
 }
+
+.retry-dropdown {
+    width: 300px;
+}
diff --git a/src-ui/src/app/components/admin/tasks/tasks.component.spec.ts b/src-ui/src/app/components/admin/tasks/tasks.component.spec.ts
index 6846e0f7c..5cf062208 100644
--- a/src-ui/src/app/components/admin/tasks/tasks.component.spec.ts
+++ b/src-ui/src/app/components/admin/tasks/tasks.component.spec.ts
@@ -32,6 +32,7 @@ import { TasksService } from 'src/app/services/tasks.service'
 import { ToastService } from 'src/app/services/toast.service'
 import { environment } from 'src/environments/environment'
 import { ConfirmDialogComponent } from '../../common/confirm-dialog/confirm-dialog.component'
+import { CheckComponent } from '../../common/input/check/check.component'
 import { PageHeaderComponent } from '../../common/page-header/page-header.component'
 import { TasksComponent, TaskTab } from './tasks.component'
 
@@ -138,6 +139,7 @@ describe('TasksComponent', () => {
         PageHeaderComponent,
         IfPermissionsDirective,
         CustomDatePipe,
+        CheckComponent,
         ConfirmDialogComponent,
       ],
       providers: [
@@ -184,8 +186,10 @@ describe('TasksComponent', () => {
       `Failed${currentTasksLength}`
     )
     expect(
-      fixture.debugElement.queryAll(By.css('table input[type="checkbox"]'))
-    ).toHaveLength(currentTasksLength + 1)
+      fixture.debugElement.queryAll(
+        By.css('table td > .form-check input[type="checkbox"]')
+      )
+    ).toHaveLength(currentTasksLength)
 
     currentTasksLength = tasks.filter(
       (t) => t.status === PaperlessTaskStatus.Complete
@@ -396,7 +400,7 @@ describe('TasksComponent', () => {
     const toastErrorSpy = jest.spyOn(toastService, 'showError')
     retrySpy.mockReturnValueOnce(of({ task_id: '123' }))
     component.retryTask(tasks[0])
-    expect(retrySpy).toHaveBeenCalledWith(tasks[0])
+    expect(retrySpy).toHaveBeenCalledWith(tasks[0], false)
     expect(toastInfoSpy).toHaveBeenCalledWith('Retrying task...')
     retrySpy.mockReturnValueOnce(throwError(() => new Error('test')))
     component.retryTask(tasks[0])
diff --git a/src-ui/src/app/components/admin/tasks/tasks.component.ts b/src-ui/src/app/components/admin/tasks/tasks.component.ts
index a3fe50447..159e403f9 100644
--- a/src-ui/src/app/components/admin/tasks/tasks.component.ts
+++ b/src-ui/src/app/components/admin/tasks/tasks.component.ts
@@ -26,6 +26,7 @@ import { CustomDatePipe } from 'src/app/pipes/custom-date.pipe'
 import { TasksService } from 'src/app/services/tasks.service'
 import { ToastService } from 'src/app/services/toast.service'
 import { ConfirmDialogComponent } from '../../common/confirm-dialog/confirm-dialog.component'
+import { CheckComponent } from '../../common/input/check/check.component'
 import { PageHeaderComponent } from '../../common/page-header/page-header.component'
 import { LoadingComponentWithPermissions } from '../../loading-component/loading.component'
 
@@ -54,6 +55,7 @@ const FILTER_TARGETS = [
     PageHeaderComponent,
     IfPermissionsDirective,
     CustomDatePipe,
+    CheckComponent,
     SlicePipe,
     FormsModule,
     ReactiveFormsModule,
@@ -106,6 +108,8 @@ export class TasksComponent
       : FILTER_TARGETS.slice(0, 1)
   }
 
+  public retryClean: boolean = false
+
   get dismissButtonText(): string {
     return this.selectedTasks.size > 0
       ? $localize`Dismiss selected`
@@ -180,7 +184,7 @@ export class TasksComponent
   }
 
   retryTask(task: PaperlessTask) {
-    this.tasksService.retryTask(task).subscribe({
+    this.tasksService.retryTask(task, this.retryClean).subscribe({
       next: () => {
         this.toastService.showInfo($localize`Retrying task...`)
       },
diff --git a/src-ui/src/app/services/tasks.service.spec.ts b/src-ui/src/app/services/tasks.service.spec.ts
index ae066cc7d..ce3ed9416 100644
--- a/src-ui/src/app/services/tasks.service.spec.ts
+++ b/src-ui/src/app/services/tasks.service.spec.ts
@@ -159,14 +159,14 @@ describe('TasksService', () => {
       date_created: new Date(),
     }
 
-    tasksService.retryTask(task).subscribe()
+    tasksService.retryTask(task, true).subscribe()
     const reloadSpy = jest.spyOn(tasksService, 'reload')
     const req = httpTestingController.expectOne(
       `${environment.apiBaseUrl}tasks/${task.id}/retry/`
     )
     expect(req.request.method).toEqual('POST')
     expect(req.request.body).toEqual({
-      task_id: task.id,
+      clean: true,
     })
     req.flush({ task_id: 12345 })
     expect(reloadSpy).toHaveBeenCalled()
diff --git a/src-ui/src/app/services/tasks.service.ts b/src-ui/src/app/services/tasks.service.ts
index bdcd00d1c..7f64432ae 100644
--- a/src-ui/src/app/services/tasks.service.ts
+++ b/src-ui/src/app/services/tasks.service.ts
@@ -81,10 +81,10 @@ export class TasksService {
       )
   }
 
-  public retryTask(task: PaperlessTask): Observable<any> {
+  public retryTask(task: PaperlessTask, clean: boolean): Observable<any> {
     return this.http
       .post(`${this.baseUrl}tasks/${task.id}/retry/`, {
-        task_id: task.id,
+        clean,
       })
       .pipe(
         takeUntil(this.unsubscribeNotifer),
diff --git a/src/documents/serialisers.py b/src/documents/serialisers.py
index 7361ca70b..8ff13ae54 100644
--- a/src/documents/serialisers.py
+++ b/src/documents/serialisers.py
@@ -2410,6 +2410,13 @@ class TasksViewSerializer(OwnedObjectSerializer):
         duplicates = _get_viewable_duplicates(document, user)
         return list(duplicates.values("id", "title", "deleted_at"))
 
+class RetryTaskSerializer(serializers.Serializer):
+    clean = serializers.BooleanField(
+        default=False,
+        write_only=True,
+        required=False,
+    )
+
 
 class RunTaskViewSerializer(serializers.Serializer[dict[str, Any]]):
     task_name = serializers.ChoiceField(
diff --git a/src/documents/views.py b/src/documents/views.py
index 9c1743b61..c667223a7 100644
--- a/src/documents/views.py
+++ b/src/documents/views.py
@@ -189,6 +189,7 @@ from documents.serialisers import NotesSerializer
 from documents.serialisers import PostDocumentSerializer
 from documents.serialisers import RemovePasswordDocumentsSerializer
 from documents.serialisers import ReprocessDocumentsSerializer
+from documents.serialisers import RetryTaskSerializer
 from documents.serialisers import RotateDocumentsSerializer
 from documents.serialisers import RunTaskViewSerializer
 from documents.serialisers import SavedViewSerializer
@@ -3471,9 +3472,16 @@ class TasksViewSet(ReadOnlyModelViewSet):
     @action(methods=["post"], detail=True)
     def retry(self, request, pk=None):
         task = self.get_object()
+
+        serializer = RetryTaskSerializer(data=request.data)
+        serializer.is_valid(raise_exception=True)
+        clean = serializer.validated_data.get("clean")
+
         try:
-            new_task_id = retry_failed_file(task.task_id, True)
+            new_task_id = retry_failed_file(task.task_id, clean)
             return Response({"task_id": new_task_id})
+        except FileNotFoundError:
+            return HttpResponseBadRequest("Original file not found")
         except Exception as e:
             logger.warning(f"An error occurred retrying task: {e!s}")
             return HttpResponseBadRequest(