diff --git a/client/src/components/Planner/BookingImportModal.tsx b/client/src/components/Planner/BookingImportModal.tsx
index 84357228..e8b38e02 100644
--- a/client/src/components/Planner/BookingImportModal.tsx
+++ b/client/src/components/Planner/BookingImportModal.tsx
@@ -7,7 +7,6 @@ import { useTranslation } from '../../i18n'
 import { useToast } from '../shared/Toast'
 import { reservationsApi, healthApi } from '../../api/client'
 import { useTripStore } from '../../store/tripStore'
-import { useSettingsStore } from '../../store/settingsStore'
 
 interface BookingImportModalProps {
   isOpen: boolean
@@ -55,7 +54,6 @@ export default function BookingImportModal({ isOpen, onClose, tripId, pushUndo }
   const { t } = useTranslation()
   const toast = useToast()
   const loadTrip = useTripStore((s) => s.loadTrip)
-  const alwaysRetryAi = useSettingsStore((s) => s.settings.llm_always_retry)
   const fileInputRef = useRef<HTMLInputElement>(null)
   const mouseDownTarget = useRef<EventTarget | null>(null)
 
@@ -139,9 +137,9 @@ export default function BookingImportModal({ isOpen, onClose, tripId, pushUndo }
     setLoading(true)
     setError('')
     try {
-      // When the user opted into "always retry with AI", rescue files kitinerary
-      // can't read automatically; otherwise offer a per-file retry in the preview.
-      const mode = aiParsing && alwaysRetryAi ? 'fallback-on-empty' : 'no-ai'
+      // Auto-rescue: whenever AI parsing is available, files kitinerary can't
+      // read fall back to the LLM automatically — no extra confirmation step.
+      const mode = aiParsing ? 'fallback-on-empty' : 'no-ai'
       const result = await reservationsApi.importBookingPreview(tripId, files, mode)
       setPreviewItems(result.items ?? [])
       setWarnings(result.warnings ?? [])
diff --git a/client/src/components/Settings/DisplaySettingsTab.tsx b/client/src/components/Settings/DisplaySettingsTab.tsx
index f3c6f9df..164b8751 100644
--- a/client/src/components/Settings/DisplaySettingsTab.tsx
+++ b/client/src/components/Settings/DisplaySettingsTab.tsx
@@ -360,37 +360,6 @@ export default function DisplaySettingsTab(): React.ReactElement {
         </div>
       </div>
 
-      {/* Always retry booking imports with AI */}
-      <div>
-        <label className="block text-sm font-medium mb-2 text-content-secondary">{t('settings.aiAlwaysRetry')}</label>
-        <div className="flex gap-3">
-          {[
-            { value: true, label: t('settings.on') || 'On' },
-            { value: false, label: t('settings.off') || 'Off' },
-          ].map(opt => (
-            <button
-              key={String(opt.value)}
-              onClick={async () => {
-                try { await updateSetting('llm_always_retry', opt.value) }
-                catch (e: unknown) { toast.error(e instanceof Error ? e.message : t('common.error')) }
-              }}
-              style={{
-                display: 'flex', alignItems: 'center', gap: 8,
-                padding: '10px 20px', borderRadius: 10, cursor: 'pointer',
-                fontFamily: 'inherit', fontSize: 14, fontWeight: 500,
-                border: (!!settings.llm_always_retry) === opt.value ? '2px solid var(--text-primary)' : '2px solid var(--border-primary)',
-                background: (!!settings.llm_always_retry) === opt.value ? 'var(--bg-hover)' : 'var(--bg-card)',
-                color: 'var(--text-primary)',
-                transition: 'all 0.15s',
-              }}
-            >
-              {opt.label}
-            </button>
-          ))}
-        </div>
-        <p className="text-xs mt-1 text-content-faint">{t('settings.aiAlwaysRetryHint')}</p>
-      </div>
-
       {/* Optimize route from accommodation */}
       <div>
         <label className="block text-sm font-medium mb-2 text-content-secondary">{t('settings.optimizeFromAccommodation')}</label>
diff --git a/client/src/types.ts b/client/src/types.ts
index b4ace95e..05cd485e 100644
--- a/client/src/types.ts
+++ b/client/src/types.ts
@@ -130,7 +130,6 @@ export interface Settings {
   dashboard_timezones?: string[]
   // AI booking-import fallback (per-user config; used when the admin has not set
   // instance-wide config on the llm_parsing addon). llm_api_key is masked on read.
-  llm_always_retry?: boolean
   llm_provider?: 'local' | 'openai' | 'anthropic'
   llm_model?: string
   llm_base_url?: string
diff --git a/server/src/services/settingsService.ts b/server/src/services/settingsService.ts
index 691fe7f1..db9a850e 100644
--- a/server/src/services/settingsService.ts
+++ b/server/src/services/settingsService.ts
@@ -31,9 +31,6 @@ export const DEFAULTABLE_USER_SETTING_KEYS = [
   'llm_base_url',
   'llm_multimodal',
   'llm_api_key',
-  // "Always retry with AI" toggle — when on, the preview auto-runs the LLM on
-  // files kitinerary returns nothing for.
-  'llm_always_retry',
 ] as const;
 
 type DefaultableKey = typeof DEFAULTABLE_USER_SETTING_KEYS[number];
@@ -47,7 +44,7 @@ const VALID_VALUES: Partial<Record<DefaultableKey, unknown[]>> = {
   llm_provider: ['local', 'openai', 'anthropic'],
 };
 
-const BOOLEAN_KEYS = new Set<DefaultableKey>(['blur_booking_codes', 'mapbox_3d_enabled', 'mapbox_quality_mode', 'llm_multimodal', 'llm_always_retry']);
+const BOOLEAN_KEYS = new Set<DefaultableKey>(['blur_booking_codes', 'mapbox_3d_enabled', 'mapbox_quality_mode', 'llm_multimodal']);
 
 function parseValue(raw: string): unknown {
   try { return JSON.parse(raw); } catch { return raw; }