diff --git a/client/src/components/BackgroundTasks/BackgroundTasksWidget.tsx b/client/src/components/BackgroundTasks/BackgroundTasksWidget.tsx
index 977833e4e..5600fc7e7 100644
--- a/client/src/components/BackgroundTasks/BackgroundTasksWidget.tsx
+++ b/client/src/components/BackgroundTasks/BackgroundTasksWidget.tsx
@@ -1,10 +1,10 @@
 import ReactDOM from 'react-dom'
-import { useEffect, useRef } from 'react'
+import { useEffect, useRef, useState } from 'react'
 import { useNavigate } from 'react-router-dom'
 import { Loader2, CheckCircle2, AlertCircle, X } from 'lucide-react'
 import { useTranslation } from '../../i18n'
 import { addListener, removeListener } from '../../api/websocket'
-import { reservationsApi } from '../../api/client'
+import { reservationsApi, healthApi } from '../../api/client'
 import { useBackgroundTasksStore, type BackgroundImportTask } from '../../store/backgroundTasksStore'
 
 /**
@@ -23,6 +23,25 @@ export default function BackgroundTasksWidget() {
   const setError = useBackgroundTasksStore((s) => s.setError)
   const requestReview = useBackgroundTasksStore((s) => s.requestReview)
   const dismiss = useBackgroundTasksStore((s) => s.dismiss)
+  const addTask = useBackgroundTasksStore((s) => s.addTask)
+
+  const [aiParsing, setAiParsing] = useState(false)
+  useEffect(() => {
+    healthApi.features().then((f) => setAiParsing(!!f.aiParsing)).catch(() => setAiParsing(false))
+  }, [])
+
+  // Re-runs the same files with force-ai: the LLM sees every file, kitinerary is skipped.
+  const retryWithAi = (task: BackgroundImportTask) => {
+    if (!task.sourceFiles || task.sourceFiles.length === 0) return
+    reservationsApi
+      .importBookingAsync(task.tripId, task.sourceFiles, 'force-ai')
+      .then(({ jobId }) => {
+        dismiss(task.id)
+        addTask({ id: jobId, tripId: task.tripId, label: task.label, total: task.sourceFiles!.length, files: task.sourceFiles, mode: 'force-ai' })
+      })
+      // 409 when the addon is enabled but this user has no model configured.
+      .catch((err) => setError(task.id, task.tripId, err?.response?.data?.error ?? t('reservations.import.error')))
+  }
 
   // On (re)load, reconcile tasks restored from localStorage with the server: a parse
   // that was still running when the page reloaded must keep its widget, so re-fetch each
@@ -136,12 +155,23 @@ export default function BackgroundTasksWidget() {
                   {t('common.import')}
                 </button>
               ) : (
-                <div style={{ fontSize: 'calc(11px * var(--fs-scale-caption, 1))', color: 'var(--text-faint)', marginTop: 1 }}>
-                  {t('reservations.import.previewEmpty')}
-                  {(task.warnings?.length ?? 0) > 0 && (
-                    <div style={{ color: '#b45309', marginTop: 3, whiteSpace: 'pre-wrap', wordBreak: 'break-word', maxHeight: 96, overflowY: 'auto' }}>
-                      {task.warnings!.join('\n')}
-                    </div>
+                <div>
+                  <div style={{ fontSize: 'calc(11px * var(--fs-scale-caption, 1))', color: 'var(--text-faint)', marginTop: 1 }}>
+                    {t('reservations.import.previewEmpty')}
+                    {(task.warnings?.length ?? 0) > 0 && (
+                      <div style={{ color: '#b45309', marginTop: 3, whiteSpace: 'pre-wrap', wordBreak: 'break-word', maxHeight: 96, overflowY: 'auto' }}>
+                        {task.warnings!.join('\n')}
+                      </div>
+                    )}
+                  </div>
+                  {aiParsing && task.mode !== 'force-ai' && task.sourceFiles && task.sourceFiles.length > 0 && (
+                    <button
+                      onClick={() => retryWithAi(task)}
+                      className="bg-surface-tertiary text-content"
+                      style={{ marginTop: 4, border: 'none', borderRadius: 8, padding: '4px 12px', fontSize: 'calc(11.5px * var(--fs-scale-caption, 1))', fontWeight: 600, cursor: 'pointer', fontFamily: 'inherit' }}
+                    >
+                      {t('reservations.import.tryAi')}
+                    </button>
                   )}
                 </div>
               )
diff --git a/client/src/components/Planner/BookingImportModal.tsx b/client/src/components/Planner/BookingImportModal.tsx
index 62c7932e2..b3e567b5d 100644
--- a/client/src/components/Planner/BookingImportModal.tsx
+++ b/client/src/components/Planner/BookingImportModal.tsx
@@ -100,7 +100,7 @@ export default function BookingImportModal({ isOpen, onClose, tripId }: BookingI
       // Keep the uploaded files so the review can attach each source document to its booking —
       // in memory for the immediate path, and in IndexedDB so it survives a reload mid-parse.
       await saveImportFiles(jobId, files)
-      addTask({ id: jobId, tripId: String(tripId), label: files.map((f) => f.name).join(', '), total: files.length, files })
+      addTask({ id: jobId, tripId: String(tripId), label: files.map((f) => f.name).join(', '), total: files.length, files, mode })
       handleClose()
     } catch (err: any) {
       setError(err?.response?.data?.error ?? t('reservations.import.error'))
diff --git a/client/src/store/backgroundTasksStore.ts b/client/src/store/backgroundTasksStore.ts
index 8b1289f05..5ffd2901f 100644
--- a/client/src/store/backgroundTasksStore.ts
+++ b/client/src/store/backgroundTasksStore.ts
@@ -1,6 +1,6 @@
 import { create } from 'zustand'
 import { persist } from 'zustand/middleware'
-import type { BookingImportPreviewItem } from '@trek/shared'
+import type { BookingImportPreviewItem, BookingImportMode } from '@trek/shared'
 
 /**
  * Tracks booking-import parses that run in the BACKGROUND (the async endpoint).
@@ -30,11 +30,13 @@ export interface BackgroundImportTask {
   /** The uploaded files this parse ran on — kept in memory so the review can attach the
    *  source document to each created booking. Not persisted (a File can't survive a reload). */
   sourceFiles?: File[]
+  /** Mode this run used — the widget only offers an AI retry if it wasn't already one. Not persisted. */
+  mode?: BookingImportMode
 }
 
 interface BackgroundTasksState {
   tasks: BackgroundImportTask[]
-  addTask: (task: { id: string; tripId: string; label: string; total: number; files?: File[] }) => void
+  addTask: (task: { id: string; tripId: string; label: string; total: number; files?: File[]; mode?: BookingImportMode }) => void
   setProgress: (id: string, tripId: string, done: number, total: number) => void
   setDone: (id: string, tripId: string, items: BookingImportPreviewItem[], warnings: string[]) => void
   setError: (id: string, tripId: string, error: string) => void
@@ -61,7 +63,7 @@ export const useBackgroundTasksStore = create<BackgroundTasksState>()(
 
       return {
         tasks: [],
-        addTask: ({ id, tripId, label, total, files }) => upsert(id, tripId, { label, total, status: 'running', done: 0, sourceFiles: files }),
+        addTask: ({ id, tripId, label, total, files, mode }) => upsert(id, tripId, { label, total, status: 'running', done: 0, sourceFiles: files, mode }),
         setProgress: (id, tripId, done, total) => upsert(id, tripId, { done, total, status: 'running' }),
         setDone: (id, tripId, items, warnings) => upsert(id, tripId, { status: 'done', items, warnings, done: items?.length ?? 0 }),
         setError: (id, tripId, error) => upsert(id, tripId, { status: 'error', error }),