Patch: Request retry, admin-level requests, and various fixes (#620)

- Add request retry in the case of a download failure, admins will be prompted to attach a new file to the request
- Add admin-level "add to requests" button in the release modal

shelfmark/core/models.py

@@ -97,6 +97,7 @@ class DownloadTask:
     # User association (multi-user support)
     user_id: Optional[int] = None  # DB user ID who queued this download
     username: Optional[str] = None  # Username for {User} template variable
+    request_id: Optional[int] = None  # Origin request ID when queued from request fulfilment
 
     # Runtime state
     priority: int = 0

shelfmark/core/requests_service.py

@@ -455,8 +455,11 @@ def fulfil_request(
     if requester is None:
         raise RequestServiceError("Requesting user not found", status_code=404)
 
+    queued_release_data = dict(selected_release_data)
+    queued_release_data["_request_id"] = request_id
+
     success, error = queue_release(
-        selected_release_data,
+        queued_release_data,
         0,
         user_id=request_row["user_id"],
         username=requester.get("username"),
@@ -476,9 +479,66 @@ def fulfil_request(
             release_data=selected_release_data,
             delivery_state="queued",
             delivery_updated_at=_now_timestamp(),
+            last_failure_reason=None,
             admin_note=normalized_admin_note,
             reviewed_by=admin_user_id,
             reviewed_at=_now_timestamp(),
         )
     except ValueError as exc:
         raise RequestServiceError(str(exc), status_code=409, code="stale_transition") from exc
+
+
+def reopen_failed_request(
+    user_db: "UserDB",
+    *,
+    request_id: int,
+    failure_reason: str | None = None,
+) -> dict[str, Any] | None:
+    """Reopen a failed fulfilled request so admins can re-approve with a new release."""
+    normalized_failure_reason = None
+    if isinstance(failure_reason, str):
+        normalized_failure_reason = failure_reason.strip() or None
+
+    with user_db._lock:
+        conn = user_db._connect()
+        try:
+            current_row = conn.execute(
+                "SELECT * FROM download_requests WHERE id = ?",
+                (request_id,),
+            ).fetchone()
+            current_request = user_db._parse_request_row(current_row)
+            if current_request is None:
+                return None
+
+            if current_request.get("status") != "fulfilled":
+                return None
+            current_delivery_state = _existing_delivery_state(current_request)
+            # Terminal hook callbacks can run before delivery-state sync persists "error".
+            # Allow reopening fulfilled requests unless they are already complete.
+            if current_delivery_state == "complete":
+                return None
+            if current_delivery_state not in {"error", "cancelled"} and normalized_failure_reason is None:
+                return None
+
+            conn.execute(
+                """
+                UPDATE download_requests
+                SET status = 'pending',
+                    delivery_state = 'none',
+                    delivery_updated_at = NULL,
+                    release_data = NULL,
+                    last_failure_reason = ?,
+                    reviewed_by = NULL,
+                    reviewed_at = NULL
+                WHERE id = ?
+                """,
+                (normalized_failure_reason, request_id),
+            )
+            updated_row = conn.execute(
+                "SELECT * FROM download_requests WHERE id = ?",
+                (request_id,),
+            ).fetchone()
+            conn.commit()
+            return user_db._parse_request_row(updated_row)
+        finally:
+            conn.close()

shelfmark/core/user_db.py

@@ -200,6 +200,8 @@ class UserDB:
             )
         if "delivery_updated_at" not in column_names:
             conn.execute("ALTER TABLE download_requests ADD COLUMN delivery_updated_at TIMESTAMP")
+        if "last_failure_reason" not in column_names:
+            conn.execute("ALTER TABLE download_requests ADD COLUMN last_failure_reason TEXT")
 
         conn.execute(
             """
@@ -614,6 +616,7 @@ class UserDB:
         "reviewed_at",
         "delivery_state",
         "delivery_updated_at",
+        "last_failure_reason",
     }
 
     def update_request(

shelfmark/download/orchestrator.py

@@ -178,6 +178,10 @@ def queue_release(
     try:
         source = release_data.get('source', 'direct_download')
         extra = release_data.get('extra', {})
+        raw_request_id = release_data.get('_request_id')
+        request_id: Optional[int] = None
+        if isinstance(raw_request_id, int) and raw_request_id > 0:
+            request_id = raw_request_id
 
         # Get author, year, preview, and content_type from top-level (preferred) or extra (fallback)
         author = release_data.get('author') or extra.get('author')
@@ -225,6 +229,7 @@ def queue_release(
             priority=priority,
             user_id=user_id,
             username=username,
+            request_id=request_id,
         )
 
         if not book_queue.add(task):
@@ -327,6 +332,7 @@ def _task_to_dict(task: DownloadTask) -> Dict[str, Any]:
         'download_path': task.download_path,
         'user_id': task.user_id,
         'username': task.username,
+        'request_id': task.request_id,
     }
 
 

shelfmark/main.py

@@ -46,6 +46,7 @@ from shelfmark.core.request_policy import (
     resolve_policy_mode,
 )
 from shelfmark.core.requests_service import (
+    reopen_failed_request,
     sync_delivery_states_from_queue_status,
 )
 from shelfmark.core.activity_service import ActivityService, build_download_item_key
@@ -1080,9 +1081,6 @@ def _notify_admin_for_terminal_download_status(*, task_id: str, status: QueueSta
 def _record_download_terminal_snapshot(task_id: str, status: QueueStatus, task: Any) -> None:
     _notify_admin_for_terminal_download_status(task_id=task_id, status=status, task=task)
 
-    if activity_service is None:
-        return
-
     final_status = _queue_status_to_final_activity_status(status)
     if final_status is None:
         return
@@ -1129,19 +1127,45 @@ def _record_download_terminal_snapshot(task_id: str, status: QueueStatus, task:
     if linked_request is not None:
         snapshot["request"] = linked_request
 
+    if activity_service is not None:
+        try:
+            activity_service.record_terminal_snapshot(
+                user_id=owner_user_id,
+                item_type="download",
+                item_key=build_download_item_key(task_id),
+                origin=origin,
+                final_status=final_status,
+                snapshot=snapshot,
+                request_id=request_id,
+                source_id=task_id,
+            )
+        except Exception as exc:
+            logger.warning("Failed to record terminal download snapshot for task %s: %s", task_id, exc)
+
+    if user_db is None or linked_request is None or request_id is None or status != QueueStatus.ERROR:
+        return
+
+    raw_error_message = getattr(task, "status_message", None)
+    fallback_reason = (
+        raw_error_message.strip()
+        if isinstance(raw_error_message, str) and raw_error_message.strip()
+        else "Download failed"
+    )
     try:
-        activity_service.record_terminal_snapshot(
-            user_id=owner_user_id,
-            item_type="download",
-            item_key=build_download_item_key(task_id),
-            origin=origin,
-            final_status=final_status,
-            snapshot=snapshot,
+        reopened_request = reopen_failed_request(
+            user_db,
             request_id=request_id,
-            source_id=task_id,
+            failure_reason=fallback_reason,
         )
+        if reopened_request is not None:
+            _emit_request_update_events([reopened_request])
     except Exception as exc:
-        logger.warning("Failed to record terminal download snapshot for task %s: %s", task_id, exc)
+        logger.warning(
+            "Failed to reopen request %s after terminal download error %s: %s",
+            request_id,
+            task_id,
+            exc,
+        )
 
 
 def _task_owned_by_actor(task: Any, *, actor_user_id: int | None, actor_username: str | None) -> bool:

src/frontend/src/App.tsx

@@ -226,6 +226,43 @@ function App() {
     socket,
   });
 
+  const dismissedDownloadTaskIds = useMemo(() => {
+    const result = new Set<string>();
+    for (const key of dismissedActivityKeys) {
+      if (typeof key !== 'string' || !key.startsWith('download:')) {
+        continue;
+      }
+      const taskId = key.substring('download:'.length).trim();
+      if (taskId) {
+        result.add(taskId);
+      }
+    }
+    return result;
+  }, [dismissedActivityKeys]);
+
+  const isDownloadTaskDismissed = useCallback((taskId: string) => {
+    return dismissedDownloadTaskIds.has(taskId);
+  }, [dismissedDownloadTaskIds]);
+
+  const statusForButtonState = useMemo(() => {
+    if (!currentStatus.complete || dismissedDownloadTaskIds.size === 0) {
+      return currentStatus;
+    }
+
+    const filteredComplete = Object.fromEntries(
+      Object.entries(currentStatus.complete).filter(([taskId]) => !dismissedDownloadTaskIds.has(taskId))
+    ) as Record<string, Book>;
+
+    if (Object.keys(filteredComplete).length === Object.keys(currentStatus.complete).length) {
+      return currentStatus;
+    }
+
+    return {
+      ...currentStatus,
+      complete: filteredComplete,
+    };
+  }, [currentStatus, dismissedDownloadTaskIds]);
+
   const showRequestsTab = useMemo(() => {
     if (requestRoleIsAdmin) {
       return true;
@@ -947,6 +984,23 @@ function App() {
     [openRequestConfirmation, refreshRequestPolicy]
   );
 
+  const handleReleaseBookRequest = useCallback(
+    async (book: Book, modalContentType: ContentType): Promise<void> => {
+      void refreshRequestPolicy();
+      const normalizedContentType = toContentType(modalContentType);
+      openRequestConfirmation({
+        book_data: buildMetadataBookRequestData(book, normalizedContentType),
+        release_data: null,
+        context: {
+          source: '*',
+          content_type: normalizedContentType,
+          request_level: 'book',
+        },
+      });
+    },
+    [openRequestConfirmation, refreshRequestPolicy]
+  );
+
   const handleReleaseModalPolicyRefresh = useCallback(() => {
     return refreshRequestPolicy({ force: true });
   }, [refreshRequestPolicy]);
@@ -1044,19 +1098,38 @@ function App() {
   const getDirectActionButtonState = useCallback(
     (bookId: string): ButtonStateInfo => {
       const baseState = getButtonState(bookId);
+      if (baseState.state === 'complete' && isDownloadTaskDismissed(bookId)) {
+        return applyDirectPolicyModeToButtonState(
+          { text: 'Download', state: 'download' },
+          getDirectPolicyMode()
+        );
+      }
       const mode = getDirectPolicyMode();
       return applyDirectPolicyModeToButtonState(baseState, mode);
     },
-    [getButtonState, getDirectPolicyMode]
+    [getButtonState, getDirectPolicyMode, isDownloadTaskDismissed]
   );
 
   const getUniversalActionButtonState = useCallback(
     (bookId: string): ButtonStateInfo => {
       const baseState = getUniversalButtonState(bookId);
+      const trackedReleaseIds = bookToReleaseMap[bookId] || [];
+      const allTrackedReleasesDismissed = trackedReleaseIds.length > 0 &&
+        trackedReleaseIds.every((releaseId) => isDownloadTaskDismissed(releaseId));
+
+      if (
+        baseState.state === 'complete' &&
+        (isDownloadTaskDismissed(bookId) || allTrackedReleasesDismissed)
+      ) {
+        return applyUniversalPolicyModeToButtonState(
+          { text: 'Get', state: 'download' },
+          getUniversalDefaultPolicyMode()
+        );
+      }
       const mode = getUniversalDefaultPolicyMode();
       return applyUniversalPolicyModeToButtonState(baseState, mode);
     },
-    [getUniversalButtonState, getUniversalDefaultPolicyMode]
+    [bookToReleaseMap, getUniversalButtonState, getUniversalDefaultPolicyMode, isDownloadTaskDismissed]
   );
 
   const bookLanguages = config?.book_languages || DEFAULT_LANGUAGES;
@@ -1263,6 +1336,11 @@ function App() {
             onClose={handleReleaseModalClose}
             onDownload={isBrowseFulfilMode ? handleBrowseFulfilDownload : handleReleaseDownload}
             onRequestRelease={isBrowseFulfilMode ? undefined : handleReleaseRequest}
+            onRequestBook={
+              isBrowseFulfilMode || !requestRoleIsAdmin
+                ? undefined
+                : handleReleaseBookRequest
+            }
             getPolicyModeForSource={isBrowseFulfilMode ? () => 'download' : (source, ct) => getSourceMode(source, ct)}
             onPolicyRefresh={handleReleaseModalPolicyRefresh}
             supportedFormats={supportedFormats}
@@ -1270,7 +1348,7 @@ function App() {
             contentType={activeReleaseContentType}
             defaultLanguages={defaultLanguageCodes}
             bookLanguages={bookLanguages}
-            currentStatus={currentStatus}
+            currentStatus={statusForButtonState}
             defaultReleaseSource={config?.default_release_source}
             onSearchSeries={isBrowseFulfilMode ? undefined : handleSearchSeries}
           />

src/frontend/src/components/ReleaseModal.tsx

@@ -194,6 +194,7 @@ interface ReleaseModalProps {
   onClose: () => void;
   onDownload: (book: Book, release: Release, contentType: ContentType) => Promise<void>;
   onRequestRelease?: (book: Book, release: Release, contentType: ContentType) => Promise<void>;
+  onRequestBook?: (book: Book, contentType: ContentType) => Promise<void>;
   getPolicyModeForSource?: (source: string, contentType: ContentType) => RequestPolicyMode;
   onPolicyRefresh?: () => Promise<unknown>;
   supportedFormats: string[];
@@ -622,6 +623,7 @@ export const ReleaseModal = ({
   onClose,
   onDownload,
   onRequestRelease,
+  onRequestBook,
   getPolicyModeForSource,
   onPolicyRefresh,
   supportedFormats,
@@ -638,6 +640,7 @@ export const ReleaseModal = ({
     ? supportedAudiobookFormats
     : supportedFormats;
   const [isClosing, setIsClosing] = useState(false);
+  const [isRequestingBook, setIsRequestingBook] = useState(false);
 
   // Available sources from plugin registry
   const [availableSources, setAvailableSources] = useState<ReleaseSource[]>([]);
@@ -699,6 +702,19 @@ export const ReleaseModal = ({
     }, 150);
   }, [onClose]);
 
+  const handleRequestBook = useCallback(async (): Promise<void> => {
+    if (!book || !onRequestBook || isRequestingBook) {
+      return;
+    }
+    setIsRequestingBook(true);
+    try {
+      await onRequestBook(book, contentType);
+      handleClose();
+    } finally {
+      setIsRequestingBook(false);
+    }
+  }, [book, onRequestBook, isRequestingBook, contentType, handleClose]);
+
   // Handle ESC key
   useEffect(() => {
     const handleEscape = (e: KeyboardEvent) => {
@@ -1511,6 +1527,21 @@ export const ReleaseModal = ({
                       </svg>
                     </a>
                   )}
+                  {onRequestBook && (
+                    <button
+                      type="button"
+                      onClick={() => {
+                        void handleRequestBook();
+                      }}
+                      disabled={isRequestingBook}
+                      className="inline-flex items-center gap-1 px-2 py-1 text-xs font-medium text-emerald-600 dark:text-emerald-400 bg-emerald-50 dark:bg-emerald-900/20 rounded-full hover:bg-emerald-100 dark:hover:bg-emerald-900/40 transition-colors disabled:cursor-not-allowed disabled:opacity-60"
+                    >
+                      <svg className="w-3 h-3" fill="none" stroke="currentColor" viewBox="0 0 24 24" strokeWidth={2}>
+                        <path strokeLinecap="round" strokeLinejoin="round" d="M12 4.5v15m7.5-7.5h-15" />
+                      </svg>
+                      {isRequestingBook ? 'Adding...' : 'Add to requests'}
+                    </button>
+                  )}
                 </div>
               </div>
             </div>

src/frontend/src/components/activity/ActivityCard.tsx

@@ -86,7 +86,7 @@ const actionKey = (action: ActivityCardAction): string => {
 
 const actionUiConfig = (
   action: ActivityCardAction
-): { title: string; className: string; icon: 'cross' | 'check' | 'stop' } => {
+): { title: string; className: string; icon: 'cross' | 'check' | 'stop' | 'retry' } => {
   switch (action.kind) {
     case 'download-remove':
       return {
@@ -139,7 +139,7 @@ const actionUiConfig = (
   }
 };
 
-const ActionIcon = ({ icon }: { icon: 'cross' | 'check' | 'stop' }) => {
+const ActionIcon = ({ icon }: { icon: 'cross' | 'check' | 'stop' | 'retry' }) => {
   if (icon === 'stop') {
     return (
       <svg className="w-4 h-4" viewBox="0 0 24 24" fill="currentColor" aria-hidden="true">
@@ -154,6 +154,13 @@ const ActionIcon = ({ icon }: { icon: 'cross' | 'check' | 'stop' }) => {
       </svg>
     );
   }
+  if (icon === 'retry') {
+    return (
+      <svg className="w-4 h-4" viewBox="0 0 24 24" fill="none" stroke="currentColor" strokeWidth="1.8" aria-hidden="true">
+        <path strokeLinecap="round" strokeLinejoin="round" d="M18.363 5.634A8.997 9.002 29.494 0 0 7.5 4.206 8.997 9.002 29.494 0 0 3.306 14.33 8.997 9.002 29.494 0 0 11.996 21a8.997 9.002 29.494 0 0 8.694-6.673m-2.327-8.693L20.87 8.14m.017-4.994v5.015m0 0h-5.013" />
+      </svg>
+    );
+  }
   return (
     <svg className="w-4 h-4" viewBox="0 0 24 24" fill="none" stroke="currentColor" strokeWidth="2.25" aria-hidden="true">
       <path strokeLinecap="round" strokeLinejoin="round" d="M6 18L18 6M6 6l12 12" />
@@ -317,7 +324,7 @@ export const ActivityCard = ({
     }
 
     return () => observer.disconnect();
-  }, [item.title, item.author]);
+  }, [item.title, item.author, isRequestDetailsOpen, isRequestRejectOpen]);
 
   const reviewRecord = item.requestRecord;
   const reviewApproveHandler = onRequestReviewApprove || onRequestApprove;
@@ -416,10 +423,13 @@ export const ActivityCard = ({
   const requiresBrowseBeforeApprove =
     reviewRecord?.request_level === 'book' || !hasAttachedRelease;
   const showSourceField = reviewRecord?.request_level === 'release';
+  const isRetryAfterFailure = Boolean(toOptionalText(reviewRecord?.last_failure_reason));
 
   const approveLabel =
     requiresBrowseBeforeApprove
-      ? 'Browse Releases To Approve'
+      ? isRetryAfterFailure
+        ? 'Browse Releases To Retry'
+        : 'Browse Releases To Approve'
       : 'Approve Attached File';
 
   const provider = toOptionalText(bookData.provider)?.toLowerCase();
@@ -509,7 +519,7 @@ export const ActivityCard = ({
       {isSelected && (
         <span
           aria-hidden="true"
-          className="absolute left-0 top-2 bottom-2 w-1 bg-sky-500/80"
+          className="absolute left-0 top-2 bottom-2 w-1 bg-gray-400/80 dark:bg-gray-500/80"
         />
       )}
       <div className="flex gap-3 items-start">
@@ -534,6 +544,8 @@ export const ActivityCard = ({
                 content={!isDetailsExpanded && titleOverflow ? titleAuthorLine : undefined}
                 delay={0}
                 position="bottom"
+                triggerClassName="block max-w-full"
+                alwaysWrap
               >
                 <p ref={titleLineRef} className={titleLineClassName}>
                   <span className="font-semibold">{titleNode}</span>
@@ -544,19 +556,27 @@ export const ActivityCard = ({
             <div className="flex-shrink-0 inline-flex items-center gap-1 -my-1">
               {actions.map((action) => {
                 const config = actionUiConfig(action);
+                const icon =
+                  action.kind === 'request-approve' && isRetryAfterFailure
+                    ? 'retry'
+                    : config.icon;
+                const actionTitle =
+                  action.kind === 'request-approve' && isRetryAfterFailure
+                    ? 'Retry'
+                    : config.title;
                 return (
                   <Tooltip
                     key={actionKey(action)}
-                    content={config.title}
+                    content={actionTitle}
                     delay={0}
                     position="bottom"
                   >
                     <IconButton
-                      title={config.title}
+                      title={actionTitle}
                       className={config.className}
                       onClick={() => runAction(action)}
                     >
-                      <ActionIcon icon={config.icon} />
+                      <ActionIcon icon={icon} />
                     </IconButton>
                   </Tooltip>
                 );
@@ -564,7 +584,7 @@ export const ActivityCard = ({
               {showRequestDetailsToggle && onRequestDetailsToggle && (
                 <IconButton
                   title={isDetailsExpanded ? 'Hide details' : 'Show details'}
-                  className="text-gray-500 hover:bg-gray-100 dark:hover:bg-gray-700"
+                  className="text-gray-500 hover-action"
                   onClick={onRequestDetailsToggle}
                 >
                   <svg
@@ -666,8 +686,12 @@ export const ActivityCard = ({
               ) : (
                 <p className="text-xs opacity-70">
                   {reviewRecord?.request_level === 'book'
-                    ? 'This is a book-level request without an attached file. Choose a release before approval.'
-                    : 'No attached release data is available. Choose a release before approval.'}
+                    ? isRetryAfterFailure
+                      ? 'Previous download failed. Choose a release before re-approving.'
+                      : 'This is a book-level request without an attached file. Choose a release before approval.'
+                    : isRetryAfterFailure
+                      ? 'Previous download failed and the attached release was cleared. Choose a release before re-approving.'
+                      : 'No attached release data is available. Choose a release before approval.'}
                 </p>
               )}
 

src/frontend/src/components/activity/ActivitySidebar.tsx

@@ -367,6 +367,23 @@ export const ActivitySidebar = ({
     });
 
     const mergedByDownloadId = new Map<string, ActivityItem>();
+    const reopenedRequestIds = new Set<number>();
+
+    visibleRequestItems.forEach((item) => {
+      if (item.kind !== 'request' || typeof item.requestId !== 'number') {
+        return;
+      }
+      const requestRecord = item.requestRecord;
+      const failureReason = requestRecord?.last_failure_reason;
+      if (
+        requestRecord?.status === 'pending' &&
+        typeof failureReason === 'string' &&
+        failureReason.trim().length > 0
+      ) {
+        reopenedRequestIds.add(item.requestId);
+      }
+    });
+
     const nextRequestItems = visibleRequestItems.map((requestItem) => {
       const linkedDownloadId = getLinkedDownloadIdFromRequestItem(requestItem);
       if (!linkedDownloadId) {
@@ -391,6 +408,15 @@ export const ActivitySidebar = ({
         return downloadItem;
       }
       return mergedByDownloadId.get(downloadId) || downloadItem;
+    }).filter((downloadItem) => {
+      if (
+        typeof downloadItem.requestId === 'number' &&
+        reopenedRequestIds.has(downloadItem.requestId) &&
+        (downloadItem.visualStatus === 'error' || downloadItem.visualStatus === 'cancelled')
+      ) {
+        return false;
+      }
+      return true;
     });
 
     return {

src/frontend/src/components/activity/activityCardModel.ts

@@ -63,16 +63,23 @@ const getRequestBadge = (item: ActivityItem, isAdmin: boolean): ActivityCardBadg
   const requestVisualStatus = item.requestRecord
     ? toRequestVisualStatus(item.requestRecord.status)
     : item.visualStatus;
+  const failureReason = item.requestRecord?.last_failure_reason?.trim() || null;
+  const hasFailureReason = requestVisualStatus === 'pending' && Boolean(failureReason);
   const hasInFlightLinkedDownload = (
     item.kind === 'download' &&
     requestVisualStatus === 'fulfilled' &&
     isActiveDownloadStatus(item.visualStatus)
   );
-  const visualStatus = hasInFlightLinkedDownload ? 'resolving' : requestVisualStatus;
+  let visualStatus: ActivityVisualStatus = hasInFlightLinkedDownload ? 'resolving' : requestVisualStatus;
+  if (hasFailureReason) {
+    visualStatus = 'error';
+  }
 
   let text = item.statusLabel;
   if (hasInFlightLinkedDownload) {
     text = 'Approved';
+  } else if (hasFailureReason) {
+    text = failureReason as string;
   } else if (requestVisualStatus === 'pending') {
     text = getPendingRequestText(item, isAdmin);
   } else if (requestVisualStatus === 'fulfilled') {

src/frontend/src/components/activity/activityMappers.ts

@@ -66,6 +66,13 @@ const getDownloadProgress = (status: ActivityVisualStatus, bookProgress: unknown
 
 export const downloadToActivityItem = (book: Book, statusKey: DownloadStatusKey): ActivityItem => {
   const visualStatus = statusKeyToVisualStatus(statusKey);
+  const requestId = (
+    typeof book.request_id === 'number' &&
+    Number.isFinite(book.request_id) &&
+    book.request_id > 0
+  )
+    ? Math.trunc(book.request_id)
+    : undefined;
   const metaLine = joinMetaParts([
     toOptionalText(book.format)?.toUpperCase(),
     toOptionalText(book.size),
@@ -92,6 +99,7 @@ export const downloadToActivityItem = (book: Book, statusKey: DownloadStatusKey)
     downloadBookId: book.id,
     downloadPath: toOptionalText(book.download_path),
     sizeRaw: toOptionalText(book.size),
+    requestId,
   };
 };
 

src/frontend/src/components/settings/SettingsContent.tsx

@@ -52,6 +52,7 @@ interface SettingsContentProps {
   customFieldContext?: {
     authMode?: string;
     onShowToast?: (message: string, type: 'success' | 'error' | 'info') => void;
+    onRefreshOverrideSummary?: () => void;
   };
 }
 
@@ -405,6 +406,7 @@ export const SettingsContent = ({
               disabledReason: disabledState.reason,
               authMode: customFieldContext?.authMode,
               onShowToast: customFieldContext?.onShowToast,
+              onRefreshOverrideSummary: customFieldContext?.onRefreshOverrideSummary,
             })
           : renderField(
               field,

src/frontend/src/components/settings/SettingsModal.tsx

@@ -44,6 +44,7 @@ export const SettingsModal = ({ isOpen, authMode, onClose, onShowToast, onSettin
 
   // Track previous isOpen state to detect modal open transition
   const prevIsOpenRef = useRef(false);
+  const overrideSummaryRequestIdRef = useRef(0);
 
   // Check for mobile viewport
   useEffect(() => {
@@ -129,32 +130,34 @@ export const SettingsModal = ({ isOpen, authMode, onClose, onShowToast, onSettin
     };
   }, [isOpen, selectedTab]);
 
+  const refreshOverrideSummaryForTab = useCallback(async (tabName: string) => {
+    const requestId = ++overrideSummaryRequestIdRef.current;
+    try {
+      const data = await getAdminSettingsOverridesSummary(tabName);
+      if (overrideSummaryRequestIdRef.current !== requestId) {
+        return;
+      }
+      setTabOverrideSummaries((prev) => ({
+        ...prev,
+        [tabName]: data.keys || {},
+      }));
+    } catch {
+      if (overrideSummaryRequestIdRef.current !== requestId) {
+        return;
+      }
+      setTabOverrideSummaries((prev) => ({
+        ...prev,
+        [tabName]: {},
+      }));
+    }
+  }, []);
+
   useEffect(() => {
     if (!isOpen || !selectedTab) {
       return;
     }
-
-    let cancelled = false;
-    getAdminSettingsOverridesSummary(selectedTab)
-      .then((data) => {
-        if (cancelled) return;
-        setTabOverrideSummaries((prev) => ({
-          ...prev,
-          [selectedTab]: data.keys || {},
-        }));
-      })
-      .catch(() => {
-        if (cancelled) return;
-        setTabOverrideSummaries((prev) => ({
-          ...prev,
-          [selectedTab]: {},
-        }));
-      });
-
-    return () => {
-      cancelled = true;
-    };
-  }, [isOpen, selectedTab]);
+    void refreshOverrideSummaryForTab(selectedTab);
+  }, [isOpen, selectedTab, refreshOverrideSummaryForTab]);
 
   // Reset to first tab when modal transitions from closed to open
   useEffect(() => {
@@ -181,10 +184,18 @@ export const SettingsModal = ({ isOpen, authMode, onClose, onShowToast, onSettin
     setShowMobileDetail(false);
   }, []);
 
+  const handleRefreshCurrentTabOverrideSummary = useCallback(() => {
+    if (!selectedTab) {
+      return;
+    }
+    void refreshOverrideSummaryForTab(selectedTab);
+  }, [selectedTab, refreshOverrideSummaryForTab]);
+
   const handleSave = useCallback(async () => {
     if (!selectedTab) return;
     const result = await saveTab(selectedTab);
     if (result.success) {
+      void refreshOverrideSummaryForTab(selectedTab);
       onShowToast?.(result.message, 'success');
       // Notify parent that settings were saved so it can refresh config
       onSettingsSaved?.();
@@ -197,7 +208,7 @@ export const SettingsModal = ({ isOpen, authMode, onClose, onShowToast, onSettin
     } else {
       onShowToast?.(result.message, 'error');
     }
-  }, [selectedTab, saveTab, onShowToast, onSettingsSaved]);
+  }, [selectedTab, saveTab, onShowToast, onSettingsSaved, refreshOverrideSummaryForTab]);
 
   const handleAction = useCallback(
     async (actionKey: string) => {
@@ -212,9 +223,13 @@ export const SettingsModal = ({ isOpen, authMode, onClose, onShowToast, onSettin
         }
         return { success: true, message: 'Opening Users tab...' };
       }
-      return executeAction(selectedTab, actionKey);
+      const result = await executeAction(selectedTab, actionKey);
+      if (result.success) {
+        void refreshOverrideSummaryForTab(selectedTab);
+      }
+      return result;
     },
-    [selectedTab, executeAction, isMobile, setSelectedTab]
+    [selectedTab, executeAction, isMobile, setSelectedTab, refreshOverrideSummaryForTab]
   );
 
   // Memoize the field change handler to prevent creating new functions on every render
@@ -285,6 +300,7 @@ export const SettingsModal = ({ isOpen, authMode, onClose, onShowToast, onSettin
         customFieldContext={{
           authMode: usersAuthMode,
           onShowToast,
+          onRefreshOverrideSummary: handleRefreshCurrentTabOverrideSummary,
         }}
       />
     ))

src/frontend/src/components/settings/customFields/UsersManagementField.tsx

@@ -20,8 +20,10 @@ export const UsersManagementField = ({
   onUiStateChange,
   authMode,
   onShowToast,
+  onRefreshOverrideSummary,
 }: CustomSettingsFieldRendererProps) => {
   const { route, openCreate, openEdit, openEditOverrides, backToList } = useUsersPanelState();
+  const activeEditRequestIdRef = useRef(0);
 
   const {
     users,
@@ -80,12 +82,30 @@ export const UsersManagementField = ({
     onEditSaveSuccess: clearEditState,
   });
 
+  const invalidateEditContextRequest = useCallback(() => {
+    activeEditRequestIdRef.current += 1;
+  }, []);
+
+  useEffect(() => {
+    return () => {
+      invalidateEditContextRequest();
+    };
+  }, [invalidateEditContextRequest]);
+
   const startEditing = async (user: AdminUser) => {
+    const requestId = activeEditRequestIdRef.current + 1;
+    activeEditRequestIdRef.current = requestId;
     beginEditing(user);
     try {
       const context = await fetchUserEditContext(user.id);
+      if (activeEditRequestIdRef.current !== requestId) {
+        return;
+      }
       applyUserEditContext(context);
     } catch {
+      if (activeEditRequestIdRef.current !== requestId) {
+        return;
+      }
       resetEditContext();
     }
   };
@@ -94,6 +114,7 @@ export const UsersManagementField = ({
 
   const handleBackToList = () => {
     onUiStateChange('routeKind', 'list');
+    invalidateEditContextRequest();
     clearEditState();
     backToList();
   };
@@ -107,6 +128,7 @@ export const UsersManagementField = ({
   const handleCreate = async () => {
     const ok = await createUser();
     if (ok) {
+      onRefreshOverrideSummary?.();
       backToList();
     }
   };
@@ -125,7 +147,10 @@ export const UsersManagementField = ({
   };
 
   const handleSyncCwa = async () => {
-    await syncCwaUsers();
+    const ok = await syncCwaUsers();
+    if (ok) {
+      onRefreshOverrideSummary?.();
+    }
   };
 
   const handleBackToEdit = () => {
@@ -151,9 +176,10 @@ export const UsersManagementField = ({
   const handleSaveUserEdit = useCallback(async () => {
     const ok = await saveEditedUser({ includeSettings: false });
     if (ok) {
+      onRefreshOverrideSummary?.();
       backToList();
     }
-  }, [backToList, saveEditedUser]);
+  }, [backToList, onRefreshOverrideSummary, saveEditedUser]);
 
   const handleSaveUserOverrides = useCallback(async () => {
     const ok = await saveEditedUser({
@@ -162,9 +188,10 @@ export const UsersManagementField = ({
       includeSettings: true,
     });
     if (ok) {
+      onRefreshOverrideSummary?.();
       backToList();
     }
-  }, [backToList, saveEditedUser]);
+  }, [backToList, onRefreshOverrideSummary, saveEditedUser]);
 
   const handleSaveUserOverridesRef = useRef(handleSaveUserOverrides);
   useEffect(() => {
@@ -182,6 +209,14 @@ export const UsersManagementField = ({
     return testAdminUserNotificationPreferences(editingUser.id, routes);
   }, [editingUser]);
 
+  const handleDeleteUser = useCallback(async (userId: number) => {
+    const ok = await deleteUser(userId);
+    if (ok) {
+      onRefreshOverrideSummary?.();
+    }
+    return ok;
+  }, [deleteUser, onRefreshOverrideSummary]);
+
   useEffect(() => {
     if (route.kind !== 'edit-overrides') {
       onUiStateChange('hasChanges', false);
@@ -227,7 +262,7 @@ export const UsersManagementField = ({
       users={users}
       loadingUsers={loading}
       loadError={loadError}
-      onRetryLoadUsers={() => void fetchUsers()}
+      onRetryLoadUsers={() => void fetchUsers({ force: true })}
       onCreate={openCreate}
       showCreateForm={route.kind === 'create'}
       createForm={createForm}
@@ -250,7 +285,7 @@ export const UsersManagementField = ({
       downloadDefaults={downloadDefaults}
       onOpenOverrides={handleOpenOverrides}
       onEdit={handleEdit}
-      onDelete={deleteUser}
+      onDelete={handleDeleteUser}
       deletingUserId={deletingUserId}
       onSyncCwa={handleSyncCwa}
       syncingCwa={syncingCwa}

src/frontend/src/components/settings/customFields/types.ts

@@ -12,6 +12,7 @@ export interface CustomSettingsFieldRendererProps {
   disabledReason?: string;
   authMode?: string;
   onShowToast?: (message: string, type: 'success' | 'error' | 'info') => void;
+  onRefreshOverrideSummary?: () => void;
 }
 
 export interface CustomSettingsFieldLayout {

src/frontend/src/components/settings/users/useUserMutations.ts

@@ -13,7 +13,7 @@ import { buildUserSettingsPayload } from './settingsPayload';
 const MIN_PASSWORD_LENGTH = 4;
 interface UseUserMutationsParams {
   onShowToast?: (message: string, type: 'success' | 'error' | 'info') => void;
-  fetchUsers: () => Promise<AdminUser[]>;
+  fetchUsers: (options?: { force?: boolean }) => Promise<AdminUser[]>;
   users: AdminUser[];
   createForm: CreateUserFormState;
   resetCreateForm: () => void;
@@ -86,7 +86,7 @@ export const useUserMutations = ({
       });
       resetCreateForm();
       onShowToast?.(`Local user ${created.username} created`, 'success');
-      await fetchUsers();
+      await fetchUsers({ force: true });
       return true;
     } catch (err) {
       return fail(err instanceof Error ? err.message : 'Failed to create user');
@@ -144,7 +144,7 @@ export const useUserMutations = ({
         includeSettings && !includeProfile && !includePassword ? 'User preferences updated' : 'User updated',
         'success',
       );
-      const refreshedUsers = await fetchUsers();
+      const refreshedUsers = await fetchUsers({ force: true });
       if (includeProfile && localAdminsBeforeSave > 0 && countLocalPasswordAdmins(refreshedUsers) === 0) {
         onShowToast?.(
           "No local admin accounts remain. Authentication will fall back to 'No Authentication' until a local admin is created.",
@@ -167,7 +167,7 @@ export const useUserMutations = ({
     try {
       await deleteAdminUser(userId);
       onShowToast?.('User deleted', 'success');
-      const refreshedUsers = await fetchUsers();
+      const refreshedUsers = await fetchUsers({ force: true });
       if (deletedUser && deletedUser.auth_source !== 'builtin') {
         onShowToast?.(
           `${authSourceLabel[deletedUser.auth_source]} users may be re-provisioned by your authentication source on a future login or sync.`,
@@ -194,7 +194,7 @@ export const useUserMutations = ({
     try {
       const result = await syncAdminCwaUsers();
       onShowToast?.(result.message || 'Users synced from CWA', 'success');
-      await fetchUsers();
+      await fetchUsers({ force: true });
       return true;
     } catch (err) {
       return fail(err instanceof Error ? err.message : 'Failed to sync users from CWA');

src/frontend/src/components/settings/users/useUsersFetch.ts

@@ -27,8 +27,12 @@ const shouldSuppressAccessToast = (message: string): boolean =>
 const toLoadErrorMessage = (err: unknown): string =>
   err instanceof Error ? err.message : 'Failed to load users';
 
-const loadUsersIntoCache = async (): Promise<AdminUser[]> => {
-  if (cachedUsers !== null) {
+interface LoadUsersOptions {
+  force?: boolean;
+}
+
+const loadUsersIntoCache = async ({ force = false }: LoadUsersOptions = {}): Promise<AdminUser[]> => {
+  if (!force && cachedUsers !== null) {
     return cachedUsers;
   }
   if (usersCacheLoadPromise) {
@@ -98,14 +102,14 @@ export const useUsersFetch = ({ onShowToast }: UseUsersFetchParams) => {
   const [loading, setLoading] = useState<boolean>(() => cachedUsers === null);
   const [loadError, setLoadError] = useState<string | null>(() => cachedLoadError);
 
-  const fetchUsers = useCallback(async (): Promise<AdminUser[]> => {
-    const hasCachedResult = cachedUsers !== null;
+  const fetchUsers = useCallback(async ({ force = false }: LoadUsersOptions = {}): Promise<AdminUser[]> => {
+    const hasCachedResult = !force && cachedUsers !== null;
     try {
       if (!hasCachedResult) {
         setLoading(true);
       }
       setLoadError(null);
-      const data = await loadUsersIntoCache();
+      const data = await loadUsersIntoCache({ force });
       setUsers(data);
       return data;
     } catch (err) {

src/frontend/src/components/shared/Tooltip.tsx

@@ -8,6 +8,8 @@ interface TooltipProps {
   delay?: number;
   className?: string;
   unstyled?: boolean;
+  triggerClassName?: string;
+  alwaysWrap?: boolean;
 }
 
 export function Tooltip({
@@ -17,15 +19,22 @@ export function Tooltip({
   delay = 200,
   className = '',
   unstyled = false,
+  triggerClassName = 'inline-flex max-w-full',
+  alwaysWrap = false,
 }: TooltipProps) {
   const [isVisible, setIsVisible] = useState(false);
   const [coords, setCoords] = useState<{ top: number; left: number } | null>(null);
   const triggerRef = useRef<HTMLDivElement>(null);
+  const tooltipRef = useRef<HTMLDivElement>(null);
   const timeoutRef = useRef<NodeJS.Timeout | null>(null);
+  const hasContent = Boolean(content);
   const isPlainTextContent = typeof content === 'string' || typeof content === 'number';
   const spacing = 6;
 
   const showTooltip = () => {
+    if (!hasContent) {
+      return;
+    }
     if (timeoutRef.current) clearTimeout(timeoutRef.current);
     timeoutRef.current = setTimeout(() => {
       if (triggerRef.current) {
@@ -67,13 +76,64 @@ export function Tooltip({
     setCoords(null);
   };
 
+  useEffect(() => {
+    if (!isVisible || !coords || !tooltipRef.current) {
+      return;
+    }
+
+    const tooltipRect = tooltipRef.current.getBoundingClientRect();
+    const viewportPadding = 6;
+
+    let deltaX = 0;
+    let deltaY = 0;
+
+    if (tooltipRect.width + viewportPadding * 2 > window.innerWidth) {
+      deltaX = viewportPadding - tooltipRect.left;
+    } else {
+      if (tooltipRect.left < viewportPadding) {
+        deltaX = viewportPadding - tooltipRect.left;
+      } else if (tooltipRect.right > window.innerWidth - viewportPadding) {
+        deltaX = (window.innerWidth - viewportPadding) - tooltipRect.right;
+      }
+    }
+
+    if (tooltipRect.height + viewportPadding * 2 > window.innerHeight) {
+      deltaY = viewportPadding - tooltipRect.top;
+    } else {
+      if (tooltipRect.top < viewportPadding) {
+        deltaY = viewportPadding - tooltipRect.top;
+      } else if (tooltipRect.bottom > window.innerHeight - viewportPadding) {
+        deltaY = (window.innerHeight - viewportPadding) - tooltipRect.bottom;
+      }
+    }
+
+    if (deltaX !== 0 || deltaY !== 0) {
+      setCoords((current) => {
+        if (!current) {
+          return current;
+        }
+        return {
+          top: current.top + deltaY,
+          left: current.left + deltaX,
+        };
+      });
+    }
+  }, [coords, isVisible]);
+
+  useEffect(() => {
+    if (!hasContent) {
+      setIsVisible(false);
+      setCoords(null);
+    }
+  }, [hasContent]);
+
   useEffect(() => {
     return () => {
       if (timeoutRef.current) clearTimeout(timeoutRef.current);
     };
   }, []);
 
-  if (!content) {
+  if (!hasContent && !alwaysWrap) {
     return <>{children}</>;
   }
 
@@ -96,12 +156,13 @@ export function Tooltip({
         onMouseLeave={hideTooltip}
         onFocusCapture={showTooltip}
         onBlurCapture={hideTooltip}
-        className="inline-flex max-w-full"
+        className={triggerClassName}
       >
         {children}
       </div>
-      {isVisible && coords && createPortal(
+      {hasContent && isVisible && coords && createPortal(
         <div
+          ref={tooltipRef}
           role="tooltip"
           className={`fixed z-[9999] pointer-events-none ${tooltipSizeClass} ${transformClass} ${className}`}
           style={{

src/frontend/src/types/index.ts

@@ -16,6 +16,7 @@ export interface DisplayField {
 // Book data types
 export interface Book {
   id: string;
+  request_id?: number;
   title: string;
   author: string;
   year?: string;
@@ -199,6 +200,7 @@ export interface RequestRecord {
   status: 'pending' | 'fulfilled' | 'rejected' | 'cancelled';
   delivery_state?: 'none' | 'unknown' | 'queued' | 'resolving' | 'locating' | 'downloading' | 'complete' | 'error' | 'cancelled';
   delivery_updated_at?: string | null;
+  last_failure_reason?: string | null;
   source_hint: string | null;
   content_type: ContentType;
   request_level: 'book' | 'release';

tests/core/test_requests_service.py

@@ -17,6 +17,7 @@ from shelfmark.core.requests_service import (
     normalize_delivery_state,
     normalize_request_level,
     normalize_request_status,
+    reopen_failed_request,
     reject_request,
     sync_delivery_states_from_queue_status,
     validate_request_level_payload,
@@ -389,6 +390,8 @@ def test_fulfil_request_queues_as_requesting_user(user_db):
     assert captured["user_id"] == alice["id"]
     assert captured["username"] == "alice"
     assert isinstance(captured["release_data"], dict)
+    assert captured["release_data"]["_request_id"] == created["id"]
+    assert "_request_id" not in (fulfilled["release_data"] or {})
 
 
 def test_fulfil_request_rejects_when_state_changes_after_queue_dispatch(user_db):
@@ -476,6 +479,93 @@ def test_fulfil_book_level_request_stores_selected_release_data(user_db):
     assert captured["username"] == "alice"
 
 
+def test_reopen_failed_request_reverts_to_pending_from_queued_and_clears_on_refulfil(user_db):
+    alice = user_db.create_user(username="alice")
+    admin = user_db.create_user(username="admin", role="admin")
+    created = create_request(
+        user_db,
+        user_id=alice["id"],
+        source_hint="prowlarr",
+        content_type="ebook",
+        request_level="release",
+        policy_mode="request_release",
+        book_data=_book_data(),
+        release_data=_release_data(),
+    )
+
+    fulfilled = fulfil_request(
+        user_db,
+        request_id=created["id"],
+        admin_user_id=admin["id"],
+        queue_release=lambda *_args, **_kwargs: (True, None),
+    )
+    assert fulfilled["status"] == "fulfilled"
+    assert fulfilled["delivery_state"] == "queued"
+    assert fulfilled["reviewed_by"] == admin["id"]
+
+    reopened = reopen_failed_request(
+        user_db,
+        request_id=created["id"],
+        failure_reason="Download failed: Timeout",
+    )
+    assert reopened is not None
+    assert reopened["status"] == "pending"
+    assert reopened["delivery_state"] == "none"
+    assert reopened["release_data"] is None
+    assert reopened["last_failure_reason"] == "Download failed: Timeout"
+    assert reopened["reviewed_by"] is None
+    assert reopened["reviewed_at"] is None
+
+    replacement_release = _release_data()
+    replacement_release["source_id"] = "release-456"
+    refulfilled = fulfil_request(
+        user_db,
+        request_id=created["id"],
+        admin_user_id=admin["id"],
+        queue_release=lambda *_args, **_kwargs: (True, None),
+        release_data=replacement_release,
+    )
+    assert refulfilled["status"] == "fulfilled"
+    assert refulfilled["release_data"]["source_id"] == "release-456"
+    assert refulfilled["last_failure_reason"] is None
+
+
+def test_reopen_failed_request_does_not_reopen_completed_delivery(user_db):
+    alice = user_db.create_user(username="alice")
+    admin = user_db.create_user(username="admin", role="admin")
+    created = create_request(
+        user_db,
+        user_id=alice["id"],
+        source_hint="prowlarr",
+        content_type="ebook",
+        request_level="release",
+        policy_mode="request_release",
+        book_data=_book_data(),
+        release_data=_release_data(),
+    )
+
+    fulfilled = fulfil_request(
+        user_db,
+        request_id=created["id"],
+        admin_user_id=admin["id"],
+        queue_release=lambda *_args, **_kwargs: (True, None),
+    )
+    assert fulfilled["status"] == "fulfilled"
+
+    user_db.update_request(
+        created["id"],
+        delivery_state="complete",
+        delivery_updated_at="2026-01-01T00:00:00+00:00",
+    )
+
+    reopened = reopen_failed_request(
+        user_db,
+        request_id=created["id"],
+        failure_reason="Download failed: Timeout",
+    )
+    assert reopened is None
+
+
 def test_sync_delivery_states_from_queue_status_updates_matching_fulfilled_requests(user_db):
     alice = user_db.create_user(username="alice")
     bob = user_db.create_user(username="bob")