src/app/api/ai-jobs/route.ts

@@ -0,0 +1,63 @@
+import { NextRequest, NextResponse } from 'next/server'
+import { requireAdmin } from '@/lib/auth'
+import { getJobQueue, getJobHistory, retryJob, cancelJob, cancelAllQueued, clearJobHistory } from '@/lib/ai-jobs'
+
+export async function GET(request: NextRequest) {
+  const auth = await requireAdmin(request)
+  if (auth instanceof NextResponse) return auth
+
+  const queue = getJobQueue()
+  const history = getJobHistory(50)
+  return NextResponse.json({ queue, history })
+}
+
+export async function POST(request: NextRequest) {
+  const auth = await requireAdmin(request)
+  if (auth instanceof NextResponse) return auth
+
+  let body: { action?: string; jobId?: string }
+  try {
+    body = await request.json()
+  } catch {
+    return NextResponse.json({ error: 'Invalid JSON body' }, { status: 400 })
+  }
+
+  const { action, jobId } = body
+
+  switch (action) {
+    case 'retry': {
+      if (!jobId || typeof jobId !== 'string') {
+        return NextResponse.json({ error: 'jobId is required' }, { status: 400 })
+      }
+      const ok = retryJob(jobId)
+      if (!ok) {
+        return NextResponse.json({ error: 'Job not found or not in failed state' }, { status: 404 })
+      }
+      return NextResponse.json({ ok: true })
+    }
+
+    case 'cancel': {
+      if (!jobId || typeof jobId !== 'string') {
+        return NextResponse.json({ error: 'jobId is required' }, { status: 400 })
+      }
+      const ok = cancelJob(jobId)
+      if (!ok) {
+        return NextResponse.json({ error: 'Job not found or not in queued state' }, { status: 404 })
+      }
+      return NextResponse.json({ ok: true })
+    }
+
+    case 'cancel-all': {
+      const cancelled = cancelAllQueued()
+      return NextResponse.json({ cancelled })
+    }
+
+    case 'clear-history': {
+      const cleared = clearJobHistory()
+      return NextResponse.json({ cleared })
+    }
+
+    default:
+      return NextResponse.json({ error: 'Unknown action' }, { status: 400 })
+  }
+}

src/app/api/ai-settings/route.ts

@@ -1,6 +1,6 @@
 import { NextRequest, NextResponse } from 'next/server'
 import { requireAdmin } from '@/lib/auth'
-import { getAiConfig, updateAiConfig, getPreferredLanguage, setPreferredLanguage } from '@/lib/app-settings'
+import { getAiConfig, updateAiConfig, getPreferredLanguage, setPreferredLanguage, getAiMaxRetries, setAiMaxRetries } from '@/lib/app-settings'
 
 export async function GET(request: NextRequest) {
   const auth = await requireAdmin(request)
@@ -8,7 +8,8 @@ export async function GET(request: NextRequest) {
 
   const config = getAiConfig()
   const preferredLanguage = getPreferredLanguage()
-  return NextResponse.json({ ...config, preferredLanguage })
+  const maxRetries = getAiMaxRetries()
+  return NextResponse.json({ ...config, preferredLanguage, maxRetries })
 }
 
 export async function PUT(request: NextRequest) {
@@ -28,6 +29,7 @@ export async function PUT(request: NextRequest) {
     promptTagger?: string
     promptExtract?: string
     promptTranslate?: string
+    maxRetries?: number
   }
   try {
     body = await request.json()
@@ -39,6 +41,7 @@ export async function PUT(request: NextRequest) {
     endpoint, model, enabled, preferredLanguage,
     modelTagging, modelDescribe, modelExtract, modelTranslate,
     promptDescribe, promptTagger, promptExtract, promptTranslate,
+    maxRetries,
   } = body
 
   if (typeof endpoint !== 'string') {
@@ -69,6 +72,10 @@ export async function PUT(request: NextRequest) {
     setPreferredLanguage(preferredLanguage.trim())
   }
 
-  const config = getAiConfig()
+  if (typeof maxRetries === 'number' && Number.isFinite(maxRetries)) {
-  return NextResponse.json({ ...config, preferredLanguage: getPreferredLanguage() })
+    setAiMaxRetries(maxRetries)
+  }
+
+  const config = getAiConfig()
+  return NextResponse.json({ ...config, preferredLanguage: getPreferredLanguage(), maxRetries: getAiMaxRetries() })
 }

src/app/api/ai-tagging/describe-bulk/route.ts

@@ -1,6 +1,10 @@
 import { NextRequest, NextResponse } from 'next/server'
 import { requireLibraryAccess } from '@/lib/auth'
-import { describeDirectoryItems } from '@/lib/ai-tagger'
+import { enqueueBulkJobs } from '@/lib/ai-jobs'
+
+const IMAGE_EXTENSIONS = new Set(['.jpg', '.jpeg', '.png', '.gif', '.webp', '.bmp', '.tiff', '.tif'])
+const VIDEO_EXTENSIONS = new Set(['.mp4', '.mkv', '.avi', '.mov', '.wmv', '.m4v', '.webm', '.flv', '.ts', '.mpg', '.mpeg'])
+const MEDIA_EXTENSIONS = new Set([...IMAGE_EXTENSIONS, ...VIDEO_EXTENSIONS])
 
 export async function POST(request: NextRequest) {
   let body: { libraryId?: string; path?: string }
@@ -18,21 +22,6 @@ export async function POST(request: NextRequest) {
   const auth = await requireLibraryAccess(request, libraryId)
   if (auth instanceof NextResponse) return auth
 
-  try {
+  const jobIds = enqueueBulkJobs(libraryId, dirPath ?? '', 'describe', 'mixed_file', MEDIA_EXTENSIONS)
-    const processed = await describeDirectoryItems(libraryId, dirPath ?? '')
+  return NextResponse.json({ jobIds, queued: jobIds.length }, { status: 202 })
-    return NextResponse.json({ processed })
-  } catch (err) {
-    const error = err as Error & { code?: string }
-    if (error.code === 'NOT_CONFIGURED') {
-      return NextResponse.json({ error: error.message }, { status: 400 })
-    }
-    if (error.code === 'NOT_FOUND') {
-      return NextResponse.json({ error: error.message }, { status: 404 })
-    }
-    if (error.code === 'INVALID_TYPE') {
-      return NextResponse.json({ error: error.message }, { status: 400 })
-    }
-    console.error('[ai-tagging/describe-bulk] Error:', error)
-    return NextResponse.json({ error: 'Failed to generate descriptions' }, { status: 502 })
-  }
 }

src/app/api/ai-tagging/describe/route.ts

@@ -1,6 +1,6 @@
 import { NextRequest, NextResponse } from 'next/server'
 import { requireLibraryAccess } from '@/lib/auth'
-import { generateItemDescription } from '@/lib/ai-tagger'
+import { enqueueJob } from '@/lib/ai-jobs'
 
 export async function POST(request: NextRequest) {
   let body: { itemKey?: string }
@@ -19,21 +19,6 @@ export async function POST(request: NextRequest) {
   const auth = await requireLibraryAccess(request, libraryId)
   if (auth instanceof NextResponse) return auth
 
-  try {
+  const jobId = enqueueJob(itemKey, 'describe', libraryId)
-    const description = await generateItemDescription(itemKey)
+  return NextResponse.json({ jobId }, { status: 202 })
-    return NextResponse.json({ description })
-  } catch (err) {
-    const error = err as Error & { code?: string }
-    if (error.code === 'NOT_CONFIGURED') {
-      return NextResponse.json({ error: error.message }, { status: 400 })
-    }
-    if (error.code === 'NOT_FOUND') {
-      return NextResponse.json({ error: error.message }, { status: 404 })
-    }
-    if (error.code === 'NO_IMAGE') {
-      return NextResponse.json({ error: error.message }, { status: 404 })
-    }
-    console.error('[ai-tagging/describe] Error:', error)
-    return NextResponse.json({ error: 'Failed to generate description' }, { status: 502 })
-  }
 }

src/app/api/ai-tagging/extract-text-bulk/route.ts

@@ -1,6 +1,8 @@
 import { NextRequest, NextResponse } from 'next/server'
 import { requireLibraryAccess } from '@/lib/auth'
-import { extractDirectoryText } from '@/lib/ai-tagger'
+import { enqueueBulkJobs } from '@/lib/ai-jobs'
+
+const IMAGE_EXTENSIONS = new Set(['.jpg', '.jpeg', '.png', '.gif', '.webp', '.bmp', '.tiff', '.tif'])
 
 export async function POST(request: NextRequest) {
   let body: { libraryId?: string; path?: string }
@@ -18,21 +20,6 @@ export async function POST(request: NextRequest) {
   const auth = await requireLibraryAccess(request, libraryId)
   if (auth instanceof NextResponse) return auth
 
-  try {
+  const jobIds = enqueueBulkJobs(libraryId, dirPath ?? '', 'extract', 'mixed_file', IMAGE_EXTENSIONS)
-    const processed = await extractDirectoryText(libraryId, dirPath ?? '')
+  return NextResponse.json({ jobIds, queued: jobIds.length }, { status: 202 })
-    return NextResponse.json({ processed })
-  } catch (err) {
-    const error = err as Error & { code?: string }
-    if (error.code === 'NOT_CONFIGURED') {
-      return NextResponse.json({ error: error.message }, { status: 400 })
-    }
-    if (error.code === 'NOT_FOUND') {
-      return NextResponse.json({ error: error.message }, { status: 404 })
-    }
-    if (error.code === 'INVALID_TYPE') {
-      return NextResponse.json({ error: error.message }, { status: 400 })
-    }
-    console.error('[ai-tagging/extract-text-bulk] Error:', error)
-    return NextResponse.json({ error: 'Failed to extract text' }, { status: 502 })
-  }
 }

src/app/api/ai-tagging/extract-text/route.ts

@@ -1,6 +1,6 @@
 import { NextRequest, NextResponse } from 'next/server'
 import { requireLibraryAccess } from '@/lib/auth'
-import { extractItemText } from '@/lib/ai-tagger'
+import { enqueueJob } from '@/lib/ai-jobs'
 
 export async function POST(request: NextRequest) {
   let body: { itemKey?: string }
@@ -19,21 +19,6 @@ export async function POST(request: NextRequest) {
   const auth = await requireLibraryAccess(request, libraryId)
   if (auth instanceof NextResponse) return auth
 
-  try {
+  const jobId = enqueueJob(itemKey, 'extract', libraryId)
-    const result = await extractItemText(itemKey)
+  return NextResponse.json({ jobId }, { status: 202 })
-    return NextResponse.json(result)
-  } catch (err) {
-    const error = err as Error & { code?: string }
-    if (error.code === 'NOT_CONFIGURED') {
-      return NextResponse.json({ error: error.message }, { status: 400 })
-    }
-    if (error.code === 'NOT_FOUND') {
-      return NextResponse.json({ error: error.message }, { status: 404 })
-    }
-    if (error.code === 'NO_IMAGE' || error.code === 'INVALID_TYPE') {
-      return NextResponse.json({ error: error.message }, { status: 400 })
-    }
-    console.error('[ai-tagging/extract-text] Error:', error)
-    return NextResponse.json({ error: 'Failed to extract text' }, { status: 502 })
-  }
 }

src/app/api/ai-tagging/route.ts

@@ -1,6 +1,6 @@
 import { NextRequest, NextResponse } from 'next/server'
 import { requireLibraryAccess } from '@/lib/auth'
-import { tagSingleItem } from '@/lib/ai-tagger'
+import { enqueueJob } from '@/lib/ai-jobs'
 
 export async function POST(request: NextRequest) {
   let body: { itemKey?: string }
@@ -19,21 +19,6 @@ export async function POST(request: NextRequest) {
   const auth = await requireLibraryAccess(request, libraryId)
   if (auth instanceof NextResponse) return auth
 
-  try {
+  const jobId = enqueueJob(itemKey, 'tag', libraryId)
-    const tagIds = await tagSingleItem(itemKey)
+  return NextResponse.json({ jobId }, { status: 202 })
-    return NextResponse.json({ tagIds })
-  } catch (err) {
-    const error = err as Error & { code?: string }
-    if (error.code === 'NOT_CONFIGURED') {
-      return NextResponse.json({ error: error.message }, { status: 400 })
-    }
-    if (error.code === 'NOT_FOUND') {
-      return NextResponse.json({ error: error.message }, { status: 404 })
-    }
-    if (error.code === 'NO_IMAGE') {
-      return NextResponse.json({ error: error.message }, { status: 404 })
-    }
-    console.error('[ai-tagging] Error tagging item:', error)
-    return NextResponse.json({ error: 'AI tagging failed' }, { status: 502 })
-  }
 }

src/app/api/ai-tagging/translate/route.ts

@@ -1,6 +1,6 @@
 import { NextRequest, NextResponse } from 'next/server'
 import { requireLibraryAccess } from '@/lib/auth'
-import { translateItemText } from '@/lib/ai-tagger'
+import { enqueueJob } from '@/lib/ai-jobs'
 
 export async function POST(request: NextRequest) {
   let body: { itemKey?: string; sourceLanguage?: string }
@@ -19,18 +19,6 @@ export async function POST(request: NextRequest) {
   const auth = await requireLibraryAccess(request, libraryId)
   if (auth instanceof NextResponse) return auth
 
-  try {
+  const jobId = enqueueJob(itemKey, 'translate', libraryId, sourceLanguage || undefined)
-    const translatedText = await translateItemText(itemKey, sourceLanguage || undefined)
+  return NextResponse.json({ jobId }, { status: 202 })
-    return NextResponse.json({ translatedText })
-  } catch (err) {
-    const error = err as Error & { code?: string }
-    if (error.code === 'NOT_CONFIGURED') {
-      return NextResponse.json({ error: error.message }, { status: 400 })
-    }
-    if (error.code === 'NOT_FOUND') {
-      return NextResponse.json({ error: error.message }, { status: 404 })
-    }
-    console.error('[ai-tagging/translate] Error:', error)
-    return NextResponse.json({ error: 'Failed to translate text' }, { status: 502 })
-  }
 }

src/app/manage/ai-tagging/page.tsx

@@ -1,6 +1,6 @@
 'use client'
 
-import { useEffect, useState, useCallback } from 'react'
+import { useEffect, useState, useCallback, useRef } from 'react'
 
 interface AiSettings {
   endpoint: string
@@ -15,6 +15,22 @@ interface AiSettings {
   promptTagger: string
   promptExtract: string
   promptTranslate: string
+  maxRetries: number
+}
+
+interface AiJob {
+  id: string
+  itemKey: string
+  libraryId: string
+  jobType: string
+  status: string
+  error: string | null
+  attempt: number
+  maxRetries: number
+  createdAt: number
+  startedAt: number | null
+  completedAt: number | null
+  itemTitle: string | null
 }
 
 interface Library {
@@ -33,11 +49,24 @@ interface LibraryOverride {
   promptTranslate: string
 }
 
+function formatElapsed(startedAt: number): string {
+  const seconds = Math.floor((Date.now() - startedAt) / 1000)
+  if (seconds < 60) return `${seconds}s`
+  const m = Math.floor(seconds / 60)
+  const s = seconds % 60
+  return `${m}m ${s}s`
+}
+
+function formatDate(ts: number): string {
+  return new Date(ts).toLocaleTimeString([], { hour: '2-digit', minute: '2-digit' })
+}
+
 export default function AiTaggingPage() {
   const [settings, setSettings] = useState<AiSettings>({
     endpoint: '', model: '', modelTagging: '', modelDescribe: '', modelExtract: '', modelTranslate: '',
     enabled: false, preferredLanguage: 'English',
     promptDescribe: '', promptTagger: '', promptExtract: '', promptTranslate: '',
+    maxRetries: 3,
   })
   const [loading, setLoading] = useState(true)
   const [saving, setSaving] = useState(false)
@@ -54,6 +83,11 @@ export default function AiTaggingPage() {
   const [librarySaving, setLibrarySaving] = useState<Record<string, boolean>>({})
   const [librarySaveResult, setLibrarySaveResult] = useState<Record<string, { ok: boolean; message: string }>>({})
 
+  // Job queue state
+  const [jobQueue, setJobQueue] = useState<AiJob[]>([])
+  const [jobHistory, setJobHistory] = useState<AiJob[]>([])
+  const [historyExpanded, setHistoryExpanded] = useState(false)
+  const jobPollRef = useRef<ReturnType<typeof setInterval> | null>(null)
   const fetchSettings = useCallback(async () => {
     try {
       const [settingsRes, librariesRes] = await Promise.all([
@@ -79,6 +113,77 @@ export default function AiTaggingPage() {
     fetchSettings()
   }, [fetchSettings])
 
+  // ─── Job queue polling ───────────────────────────────────────────────────────
+
+  const fetchJobs = useCallback(async () => {
+    try {
+      const res = await fetch('/api/ai-jobs')
+      if (res.ok) {
+        const data: { queue: AiJob[]; history: AiJob[] } = await res.json()
+        setJobQueue(data.queue)
+        setJobHistory(data.history)
+      }
+    } catch {
+      // ignore
+    }
+  }, [])
+
+  useEffect(() => {
+    fetchJobs()
+  }, [fetchJobs])
+
+  // Poll every 2s while there are active jobs
+  useEffect(() => {
+    const hasActive = jobQueue.length > 0
+    if (hasActive) {
+      jobPollRef.current = setInterval(fetchJobs, 2000)
+    } else {
+      if (jobPollRef.current) {
+        clearInterval(jobPollRef.current)
+        jobPollRef.current = null
+      }
+    }
+    return () => {
+      if (jobPollRef.current) clearInterval(jobPollRef.current)
+    }
+  }, [jobQueue.length, fetchJobs])
+
+  const handleRetryJob = async (jobId: string) => {
+    await fetch('/api/ai-jobs', {
+      method: 'POST',
+      headers: { 'Content-Type': 'application/json' },
+      body: JSON.stringify({ action: 'retry', jobId }),
+    })
+    fetchJobs()
+  }
+
+  const handleCancelJob = async (jobId: string) => {
+    await fetch('/api/ai-jobs', {
+      method: 'POST',
+      headers: { 'Content-Type': 'application/json' },
+      body: JSON.stringify({ action: 'cancel', jobId }),
+    })
+    fetchJobs()
+  }
+
+  const handleCancelAll = async () => {
+    await fetch('/api/ai-jobs', {
+      method: 'POST',
+      headers: { 'Content-Type': 'application/json' },
+      body: JSON.stringify({ action: 'cancel-all' }),
+    })
+    fetchJobs()
+  }
+
+  const handleClearHistory = async () => {
+    await fetch('/api/ai-jobs', {
+      method: 'POST',
+      headers: { 'Content-Type': 'application/json' },
+      body: JSON.stringify({ action: 'clear-history' }),
+    })
+    fetchJobs()
+  }
+
   const fetchLibraryOverrides = useCallback(async (libraryId: string) => {
     try {
       const res = await fetch(`/api/ai-settings/library/${libraryId}`)
@@ -201,12 +306,182 @@ export default function AiTaggingPage() {
   return (
     <div className="max-w-2xl">
       <h1 className="text-2xl font-semibold mb-1" style={{ color: 'var(--text-primary)' }}>
-        AI Tagging
+        AI Integrations
       </h1>
       <p className="text-sm mb-8" style={{ color: 'var(--text-secondary)' }}>
-        Automatically tag media using a vision-capable LLM on your network.
+        Manage AI-powered tagging, descriptions, and text extraction.
       </p>
 
+      {/* ─── Job Queue ─────────────────────────────────────────────────────── */}
+      <Section title="Job Queue">
+        {(() => {
+          const running = jobQueue.filter((j) => j.status === 'running')
+          const queued = jobQueue.filter((j) => j.status === 'queued')
+          if (running.length === 0 && queued.length === 0) {
+            return (
+              <p className="text-sm" style={{ color: 'var(--text-secondary)' }}>
+                No active jobs.
+              </p>
+            )
+          }
+          return (
+            <div className="flex flex-col gap-3">
+              <div className="flex items-center justify-between">
+                <p className="text-xs" style={{ color: 'var(--text-secondary)' }}>
+                  {running.length > 0 && <span>{running.length} running</span>}
+                  {running.length > 0 && queued.length > 0 && ', '}
+                  {queued.length > 0 && <span>{queued.length} queued</span>}
+                </p>
+                {queued.length > 0 && (
+                  <button
+                    type="button"
+                    onClick={handleCancelAll}
+                    className="text-xs px-2 py-1 rounded transition-colors"
+                    style={{ color: '#fca5a5', backgroundColor: '#7f1d1d33' }}
+                  >
+                    Cancel All
+                  </button>
+                )}
+              </div>
+              <div className="flex flex-col divide-y" style={{ borderColor: 'var(--border)' }}>
+                {running.map((job) => (
+                  <div key={job.id} className="flex items-center gap-3 py-2">
+                    <span
+                      className="text-xs px-2 py-0.5 rounded-full animate-pulse"
+                      style={{ backgroundColor: '#16a34a33', color: '#4ade80' }}
+                    >
+                      Running
+                    </span>
+                    <span className="text-sm flex-1 truncate" style={{ color: 'var(--text-primary)' }}>
+                      {job.itemTitle || job.itemKey}
+                    </span>
+                    <span className="text-xs" style={{ color: 'var(--text-secondary)' }}>
+                      {job.jobType}
+                    </span>
+                    {job.startedAt && (
+                      <span className="text-xs tabular-nums" style={{ color: 'var(--text-secondary)' }}>
+                        {formatElapsed(job.startedAt)}
+                      </span>
+                    )}
+                  </div>
+                ))}
+                {queued.map((job) => (
+                  <div key={job.id} className="flex items-center gap-3 py-2">
+                    <span
+                      className="text-xs px-2 py-0.5 rounded-full"
+                      style={{ backgroundColor: 'var(--border)', color: 'var(--text-secondary)' }}
+                    >
+                      Queued
+                    </span>
+                    <span className="text-sm flex-1 truncate" style={{ color: 'var(--text-primary)' }}>
+                      {job.itemTitle || job.itemKey}
+                    </span>
+                    <span className="text-xs" style={{ color: 'var(--text-secondary)' }}>
+                      {job.jobType}
+                    </span>
+                    <button
+                      type="button"
+                      onClick={() => handleCancelJob(job.id)}
+                      className="text-xs px-2 py-0.5 rounded transition-colors"
+                      style={{ color: 'var(--text-secondary)' }}
+                    >
+                      ✕
+                    </button>
+                  </div>
+                ))}
+              </div>
+            </div>
+          )
+        })()}
+      </Section>
+
+      {/* ─── Job History ───────────────────────────────────────────────────── */}
+      <Section title="Job History">
+        {jobHistory.length === 0 ? (
+          <p className="text-sm" style={{ color: 'var(--text-secondary)' }}>
+            No recent jobs.
+          </p>
+        ) : (
+          <div className="flex flex-col gap-3">
+            <button
+              type="button"
+              onClick={() => setHistoryExpanded((v) => !v)}
+              className="flex items-center gap-2 text-left"
+              style={{ color: 'var(--text-secondary)' }}
+            >
+              <span
+                className="text-xs transition-transform inline-block"
+                style={{ transform: historyExpanded ? 'rotate(180deg)' : 'rotate(0deg)' }}
+              >
+                ▾
+              </span>
+              <span className="text-xs">
+                {jobHistory.length} recent job{jobHistory.length !== 1 ? 's' : ''}
+              </span>
+            </button>
+            {historyExpanded && (
+              <>
+                <div className="flex flex-col divide-y" style={{ borderColor: 'var(--border)' }}>
+                  {jobHistory.map((job) => (
+                    <div key={job.id} className="flex items-center gap-3 py-2">
+                      <span
+                        className="text-xs px-2 py-0.5 rounded-full whitespace-nowrap"
+                        style={{
+                          backgroundColor: job.status === 'completed' ? '#14532d33' : '#7f1d1d33',
+                          color: job.status === 'completed' ? '#4ade80' : '#fca5a5',
+                        }}
+                      >
+                        {job.status === 'completed' ? 'Done' : 'Failed'}
+                      </span>
+                      <div className="flex-1 min-w-0">
+                        <span className="text-sm truncate block" style={{ color: 'var(--text-primary)' }}>
+                          {job.itemTitle || job.itemKey}
+                        </span>
+                        {job.status === 'failed' && job.error && (
+                          <span className="text-xs truncate block" style={{ color: '#fca5a5' }}>
+                            {job.error}
+                          </span>
+                        )}
+                      </div>
+                      <span className="text-xs whitespace-nowrap" style={{ color: 'var(--text-secondary)' }}>
+                        {job.jobType}
+                      </span>
+                      <span className="text-xs whitespace-nowrap" style={{ color: 'var(--text-secondary)' }}>
+                        {job.completedAt ? formatDate(job.completedAt) : ''}
+                      </span>
+                      {job.status === 'failed' && (
+                        <button
+                          type="button"
+                          onClick={() => handleRetryJob(job.id)}
+                          className="text-xs px-2 py-0.5 rounded transition-colors whitespace-nowrap"
+                          style={{ color: 'var(--accent)' }}
+                        >
+                          Retry
+                        </button>
+                      )}
+                    </div>
+                  ))}
+                </div>
+                <div>
+                  <button
+                    type="button"
+                    onClick={handleClearHistory}
+                    className="text-xs px-3 py-1.5 rounded-lg transition-colors"
+                    style={{
+                      backgroundColor: 'var(--surface)',
+                      color: 'var(--text-secondary)',
+                      border: '1px solid var(--border)',
+                    }}
+                  >
+                    Clear History
+                  </button>
+                </div>
+              </>
+            )}
+          </div>
+        )}
+      </Section>
+
       <Section title="Connection">
         {loading ? (
           <LoadingRows />
@@ -365,6 +640,29 @@ export default function AiTaggingPage() {
               </p>
             </Field>
 
+            <Field label="Max Retries">
+              <input
+                type="number"
+                min={0}
+                max={10}
+                value={settings.maxRetries}
+                onChange={(e) =>
+                  setSettings((s) => ({ ...s, maxRetries: Math.max(0, Math.min(10, parseInt(e.target.value) || 0)) }))
+                }
+                className="w-24 rounded-lg px-3 py-2 text-sm outline-none focus:ring-2"
+                style={{
+                  backgroundColor: 'var(--background)',
+                  border: '1px solid var(--border)',
+                  color: 'var(--text-primary)',
+                }}
+                onFocus={(e) => ((e.currentTarget as HTMLElement).style.borderColor = 'var(--accent)')}
+                onBlur={(e) => ((e.currentTarget as HTMLElement).style.borderColor = 'var(--border)')}
+              />
+              <p className="mt-1 text-xs" style={{ color: 'var(--text-secondary)' }}>
+                Number of times to automatically retry a failed AI job before marking it as failed (0–10).
+              </p>
+            </Field>
+
             {saveError && (
               <p
                 className="text-sm rounded-lg px-3 py-2"

src/components/DoomScrollView.tsx

@@ -196,6 +196,11 @@ export default function DoomScrollView({ items, videoContext = 'mixed', onClose,
         const data = await res.json().catch(() => ({}))
         throw new Error((data as { error?: string }).error ?? 'Extraction failed')
       }
+      if (res.status === 202) {
+        setExtractError('Queued — check AI Integrations for progress')
+        setTimeout(() => setExtractError(null), 4000)
+        return
+      }
       const result = await res.json()
       setExtractedText(result.extractedText || null)
       setTranslatedText(result.translatedText || null)

src/components/ManageSubNav.tsx

@@ -8,7 +8,7 @@ const TABS = [
   { href: '/manage/tags', label: 'Tags' },
   { href: '/manage/users', label: 'Users' },
   { href: '/manage/scanning', label: 'Scanning' },
-  { href: '/manage/ai-tagging', label: 'AI Tagging' },
+  { href: '/manage/ai-tagging', label: 'AI Integrations' },
 ]
 
 export default function ManageSubNav() {

src/components/mixed/ImageLightbox.tsx

@@ -269,6 +269,11 @@ export default function ImageLightbox({ url, name, onClose, onPrev, onNext, item
                         const data = await res.json().catch(() => ({}))
                         throw new Error((data as { error?: string }).error ?? 'Failed to extract text')
                       }
+                      if (res.status === 202) {
+                        setExtractError('Queued — check AI Integrations for progress')
+                        setTimeout(() => setExtractError(null), 4000)
+                        return
+                      }
                       const result = await res.json()
                       setExtractedText(result.extractedText || null)
                       setEditedExtractedText(result.extractedText || '')
@@ -385,8 +390,10 @@ export default function ImageLightbox({ url, name, onClose, onPrev, onNext, item
                               const data = await res.json().catch(() => ({}))
                               throw new Error((data as { error?: string }).error ?? 'Failed to translate')
                             }
+                            if (res.status !== 202) {
                               const result = await res.json()
                               setTranslatedText(result.translatedText || null)
+                            }
                           } catch {
                             // ignore
                           } finally {

src/components/tags/TagSelector.tsx

@@ -192,6 +192,11 @@ export default function TagSelector({ itemKey, onTagsChanged, refreshKey }: Prop
         const data = await res.json().catch(() => ({}))
         throw new Error((data as { error?: string }).error ?? 'Failed to generate description')
       }
+      if (res.status === 202) {
+        setDescError('Queued — check AI Integrations for progress')
+        setTimeout(() => setDescError(null), 4000)
+        return
+      }
       const { description } = await res.json()
       setAiDescription(description)
     } catch (err) {

src/instrumentation.ts

@@ -5,5 +5,8 @@ export async function register() {
 
     const { startScheduler } = await import('./lib/scheduler')
     startScheduler()
+
+    const { initJobProcessor } = await import('./lib/ai-jobs')
+    initJobProcessor()
   }
 }

src/lib/ai-jobs.ts

@@ -0,0 +1,351 @@
+import crypto from 'crypto'
+import { getDb } from './db'
+import { getAiMaxRetries } from './app-settings'
+import { tagSingleItem, generateItemDescription, extractItemText, translateItemText } from './ai-tagger'
+
+export type AiJobType = 'tag' | 'describe' | 'extract' | 'translate'
+export type AiJobStatus = 'queued' | 'running' | 'completed' | 'failed'
+
+export interface AiJob {
+  id: string
+  itemKey: string
+  libraryId: string
+  jobType: AiJobType
+  status: AiJobStatus
+  error: string | null
+  attempt: number
+  maxRetries: number
+  createdAt: number
+  startedAt: number | null
+  completedAt: number | null
+  itemTitle: string | null
+}
+
+interface AiJobRow {
+  id: string
+  item_key: string
+  library_id: string
+  job_type: string
+  status: string
+  error: string | null
+  attempt: number
+  max_retries: number
+  created_at: number
+  started_at: number | null
+  completed_at: number | null
+  item_title: string | null
+}
+
+function rowToJob(row: AiJobRow): AiJob {
+  return {
+    id: row.id,
+    itemKey: row.item_key,
+    libraryId: row.library_id,
+    jobType: row.job_type as AiJobType,
+    status: row.status as AiJobStatus,
+    error: row.error,
+    attempt: row.attempt,
+    maxRetries: row.max_retries,
+    createdAt: row.created_at,
+    startedAt: row.started_at,
+    completedAt: row.completed_at,
+    itemTitle: row.item_title,
+  }
+}
+
+/**
+ * Look up the title of a media item for display purposes.
+ */
+function resolveItemTitle(itemKey: string): string | null {
+  const db = getDb()
+  const row = db
+    .prepare('SELECT title FROM media_items WHERE item_key = ?')
+    .get(itemKey) as { title: string | null } | undefined
+  return row?.title ?? null
+}
+
+// ─── Enqueue ─────────────────────────────────────────────────────────────────
+
+/**
+ * Enqueue an AI job. Deduplicates: if a queued/running job with the same
+ * item_key + job_type already exists, returns its ID instead.
+ */
+export function enqueueJob(
+  itemKey: string,
+  jobType: AiJobType,
+  libraryId: string,
+  sourceLanguage?: string,
+): string {
+  const db = getDb()
+
+  // Deduplication: check for existing queued/running job
+  const existing = db
+    .prepare(
+      `SELECT id FROM ai_jobs
+       WHERE item_key = ? AND job_type = ? AND status IN ('queued', 'running')`
+    )
+    .get(itemKey, jobType) as { id: string } | undefined
+  if (existing) return existing.id
+
+  const id = crypto.randomUUID()
+  const maxRetries = getAiMaxRetries()
+  const title = resolveItemTitle(itemKey)
+
+  // Store sourceLanguage in the error field temporarily for translate jobs
+  // (it's null at creation, so we repurpose it briefly — cleared when the job runs)
+  const metadata = jobType === 'translate' && sourceLanguage ? sourceLanguage : null
+
+  db.prepare(
+    `INSERT INTO ai_jobs (id, item_key, library_id, job_type, status, error, attempt, max_retries, created_at, item_title)
+     VALUES (?, ?, ?, ?, 'queued', ?, 0, ?, ?, ?)`
+  ).run(id, itemKey, libraryId, jobType, metadata, maxRetries, Date.now(), title)
+
+  // Wake the processor
+  wakeProcessor()
+
+  return id
+}
+
+/**
+ * Enqueue jobs for all media items in a directory (for bulk operations).
+ * Returns the list of job IDs created.
+ */
+export function enqueueBulkJobs(
+  libraryId: string,
+  dirPath: string,
+  jobType: AiJobType,
+  itemTypeFilter?: string,
+  extFilter?: Set<string>,
+): string[] {
+  const db = getDb()
+  const prefix = dirPath
+    ? `${libraryId}:mixed_file:${encodeURIComponent(dirPath + '/')}`
+    : `${libraryId}:mixed_file:`
+
+  const items = db
+    .prepare('SELECT item_key, item_type, file_path FROM media_items WHERE item_key LIKE ? AND item_type = ?')
+    .all(`${prefix}%`, itemTypeFilter ?? 'mixed_file') as Array<{ item_key: string; item_type: string; file_path: string | null }>
+
+  const path = require('path')
+  const jobIds: string[] = []
+
+  for (const item of items) {
+    if (!item.file_path) continue
+    if (extFilter) {
+      const ext = path.extname(item.file_path).toLowerCase()
+      if (!extFilter.has(ext)) continue
+    }
+    const jobId = enqueueJob(item.item_key, jobType, libraryId)
+    jobIds.push(jobId)
+  }
+
+  return jobIds
+}
+
+// ─── Query ───────────────────────────────────────────────────────────────────
+
+export function getJobQueue(): AiJob[] {
+  const db = getDb()
+  const rows = db
+    .prepare(
+      `SELECT * FROM ai_jobs
+       WHERE status IN ('running', 'queued')
+       ORDER BY
+         CASE status WHEN 'running' THEN 0 ELSE 1 END,
+         created_at ASC`
+    )
+    .all() as AiJobRow[]
+  return rows.map(rowToJob)
+}
+
+export function getJobHistory(limit = 50): AiJob[] {
+  const db = getDb()
+  const rows = db
+    .prepare(
+      `SELECT * FROM ai_jobs
+       WHERE status IN ('completed', 'failed')
+       ORDER BY completed_at DESC
+       LIMIT ?`
+    )
+    .all(limit) as AiJobRow[]
+  return rows.map(rowToJob)
+}
+
+export function getJob(jobId: string): AiJob | null {
+  const db = getDb()
+  const row = db
+    .prepare('SELECT * FROM ai_jobs WHERE id = ?')
+    .get(jobId) as AiJobRow | undefined
+  return row ? rowToJob(row) : null
+}
+
+// ─── Actions ─────────────────────────────────────────────────────────────────
+
+export function retryJob(jobId: string): boolean {
+  const db = getDb()
+  const result = db
+    .prepare(
+      `UPDATE ai_jobs SET status = 'queued', error = NULL, attempt = 0, started_at = NULL, completed_at = NULL
+       WHERE id = ? AND status = 'failed'`
+    )
+    .run(jobId)
+  if (result.changes > 0) {
+    wakeProcessor()
+    return true
+  }
+  return false
+}
+
+export function cancelJob(jobId: string): boolean {
+  const db = getDb()
+  const result = db
+    .prepare("DELETE FROM ai_jobs WHERE id = ? AND status = 'queued'")
+    .run(jobId)
+  return result.changes > 0
+}
+
+export function cancelAllQueued(): number {
+  const db = getDb()
+  const result = db
+    .prepare("DELETE FROM ai_jobs WHERE status = 'queued'")
+    .run()
+  return result.changes
+}
+
+export function clearJobHistory(): number {
+  const db = getDb()
+  const result = db
+    .prepare("DELETE FROM ai_jobs WHERE status IN ('completed', 'failed')")
+    .run()
+  return result.changes
+}
+
+// ─── Processor ───────────────────────────────────────────────────────────────
+
+let processorRunning = false
+let processorWake: (() => void) | null = null
+
+function wakeProcessor(): void {
+  if (processorWake) {
+    processorWake()
+  } else if (!processorRunning) {
+    runProcessor()
+  }
+}
+
+async function processNextJob(): Promise<boolean> {
+  const db = getDb()
+
+  const row = db
+    .prepare(
+      `SELECT * FROM ai_jobs
+       WHERE status = 'queued'
+       ORDER BY created_at ASC
+       LIMIT 1`
+    )
+    .get() as AiJobRow | undefined
+
+  if (!row) return false
+
+  const now = Date.now()
+
+  // Extract sourceLanguage for translate jobs (stored in error field at enqueue)
+  const sourceLanguage = row.job_type === 'translate' ? row.error : null
+
+  db.prepare(
+    "UPDATE ai_jobs SET status = 'running', started_at = ?, error = NULL WHERE id = ?"
+  ).run(now, row.id)
+
+  try {
+    switch (row.job_type) {
+      case 'tag':
+        await tagSingleItem(row.item_key)
+        break
+      case 'describe':
+        await generateItemDescription(row.item_key)
+        break
+      case 'extract':
+        await extractItemText(row.item_key)
+        break
+      case 'translate':
+        await translateItemText(row.item_key, sourceLanguage || undefined)
+        break
+    }
+
+    db.prepare(
+      "UPDATE ai_jobs SET status = 'completed', completed_at = ? WHERE id = ?"
+    ).run(Date.now(), row.id)
+  } catch (err) {
+    const errorMessage = err instanceof Error ? err.message : String(err)
+    const attempt = row.attempt + 1
+
+    if (attempt < row.max_retries) {
+      // Re-queue for retry
+      db.prepare(
+        "UPDATE ai_jobs SET status = 'queued', attempt = ?, error = ?, started_at = NULL WHERE id = ?"
+      ).run(attempt, errorMessage, row.id)
+    } else {
+      // Final failure
+      db.prepare(
+        "UPDATE ai_jobs SET status = 'failed', attempt = ?, error = ?, completed_at = ? WHERE id = ?"
+      ).run(attempt, errorMessage, Date.now(), row.id)
+    }
+
+    console.warn(
+      `[ai-jobs] Job ${row.id} (${row.job_type} for "${row.item_key}") failed (attempt ${attempt}/${row.max_retries}):`,
+      errorMessage
+    )
+  }
+
+  return true
+}
+
+async function runProcessor(): Promise<void> {
+  if (processorRunning) return
+  processorRunning = true
+  console.log('[ai-jobs] Processor started')
+
+  try {
+    while (true) {
+      const hadWork = await processNextJob()
+      if (!hadWork) {
+        // Wait for a wake signal or timeout after 60s (then check again for safety)
+        await new Promise<void>((resolve) => {
+          processorWake = resolve
+          setTimeout(() => {
+            processorWake = null
+            resolve()
+          }, 60_000)
+        })
+        processorWake = null
+      }
+    }
+  } catch (err) {
+    console.error('[ai-jobs] Processor crashed:', err)
+  } finally {
+    processorRunning = false
+    console.log('[ai-jobs] Processor stopped')
+  }
+}
+
+/**
+ * Initialize the job processor. Called on server startup.
+ * Resets any jobs stuck in 'running' state (from a previous crash) back to 'queued'.
+ */
+export function initJobProcessor(): void {
+  const db = getDb()
+  const result = db
+    .prepare("UPDATE ai_jobs SET status = 'queued', started_at = NULL WHERE status = 'running'")
+    .run()
+  if (result.changes > 0) {
+    console.log(`[ai-jobs] Reset ${result.changes} stuck running job(s) to queued`)
+  }
+
+  // Check if there are any queued jobs and start the processor
+  const pending = db
+    .prepare("SELECT COUNT(*) as count FROM ai_jobs WHERE status = 'queued'")
+    .get() as { count: number }
+  if (pending.count > 0) {
+    runProcessor()
+  }
+}

src/lib/ai-tagger.ts

@@ -225,7 +225,7 @@ async function callVisionApi(
 
 /**
  * Run AI tagging for a single library. Called after the scanner finishes.
- * Processes up to BATCH_LIMIT untagged items per invocation.
+ * Enqueues up to BATCH_LIMIT untagged items as jobs for the processor.
  */
 export async function runAiTagging(library: Library, libraryRoot: string): Promise<void> {
   const config = getEffectiveAiConfig(library.id)
@@ -234,14 +234,10 @@ export async function runAiTagging(library: Library, libraryRoot: string): Promi
 
   const activeCategoryIds = new Set(getActiveCategoryIdsForLibrary(library.id))
   const allTags = getTags()
-  const allCategories = getCategories()
 
   const tags = allTags.filter((t) => activeCategoryIds.has(t.categoryId))
-  const categories = allCategories.filter((c) => activeCategoryIds.has(c.id))
   if (tags.length === 0) return
 
-  const validTagIds = new Set(tags.map((t) => t.id))
-
   const db = getDb()
   const untaggedItems = db
     .prepare(
@@ -254,18 +250,13 @@ export async function runAiTagging(library: Library, libraryRoot: string): Promi
 
   if (untaggedItems.length === 0) return
 
-  console.log(`[ai-tagger] Processing ${untaggedItems.length} items in library "${library.name}"`)
+  // Import enqueueJob lazily to avoid circular dependency
+  const { enqueueJob } = await import('./ai-jobs')
 
-  let tagged = 0
+  let enqueued = 0
-  let consecutiveFailures = 0
   const markTagged = db.prepare('UPDATE media_items SET ai_tagged_at = ? WHERE item_key = ?')
 
   for (const item of untaggedItems) {
-    if (consecutiveFailures >= MAX_CONSECUTIVE_FAILURES) {
-      console.warn(`[ai-tagger] Aborting after ${MAX_CONSECUTIVE_FAILURES} consecutive failures`)
-      break
-    }
-
     const resolvedMedia = resolveItemImage(libraryRoot, item)
     if (!resolvedMedia) {
       // No image or video available — mark as tagged so we don't retry every scan
@@ -273,48 +264,14 @@ export async function runAiTagging(library: Library, libraryRoot: string): Promi
       continue
     }
 
-    try {
+    enqueueJob(item.item_key, 'tag', library.id)
-      let base64Images: string[]
+    // Mark as tagged immediately so subsequent scans don't re-enqueue
-      if (resolvedMedia.mediaType === 'video') {
-        const framePaths = await getVideoFramePaths(resolvedMedia.path, library.id, VIDEO_FRAME_PERCENTAGES)
-        base64Images = framePaths.map((p) => fs.readFileSync(p, 'base64'))
-      } else {
-        const thumbnailPath = await getAiImagePath(resolvedMedia.path, library.id)
-        base64Images = [fs.readFileSync(thumbnailPath, 'base64')]
-      }
-
-      const { tags: currentItemTags } = getResolvedTagsForItem(item.item_key)
-      const aiFields = getAiFields(item.item_key)
-      const systemPrompt = buildTagPrompt(tags, categories, {
-        currentTags: currentItemTags,
-        mediaContext: resolvedMedia.mediaType,
-        aiDescription: aiFields.aiDescription,
-        extractedText: aiFields.extractedTextTranslated ?? aiFields.extractedText,
-        customInstruction: config.promptTagger || undefined,
-      })
-
-      const suggestedIds = await callVisionApi(config.endpoint, taggingModel, base64Images, systemPrompt)
-
-      // Filter to valid tags only
-      const validIds = suggestedIds.filter((id) => validTagIds.has(id))
-      for (const tagId of validIds) {
-        addTagToItem(item.item_key, tagId)
-      }
-
     markTagged.run(Date.now(), item.item_key)
-      tagged++
+    enqueued++
-      consecutiveFailures = 0
-    } catch (err) {
-      consecutiveFailures++
-      console.warn(
-        `[ai-tagger] Failed to tag "${item.item_key}":`,
-        err instanceof Error ? err.message : err
-      )
-    }
   }
 
-  if (tagged > 0) {
+  if (enqueued > 0) {
-    console.log(`[ai-tagger] Tagged ${tagged}/${untaggedItems.length} items in library "${library.name}"`)
+    console.log(`[ai-tagger] Enqueued ${enqueued} tagging jobs for library "${library.name}"`)
   }
 }
 

src/lib/app-settings.ts

@@ -202,3 +202,15 @@ export function getEffectiveAiConfig(libraryId: string): AiConfig {
     promptTranslate: overrides.promptTranslate || global.promptTranslate,
   }
 }
+
+// ─── AI Max Retries ──────────────────────────────────────────────────────────
+
+export function getAiMaxRetries(): number {
+  const raw = getSetting('ai_max_retries')
+  const parsed = parseInt(raw ?? '3', 10)
+  return Number.isFinite(parsed) && parsed >= 0 ? parsed : 3
+}
+
+export function setAiMaxRetries(n: number): void {
+  setSetting('ai_max_retries', String(Math.max(0, Math.floor(n))))
+}

src/lib/db.ts

@@ -105,6 +105,7 @@ function initDb(db: Database.Database): void {
   migrateMediaItemsAiTagged(db)
   migrateMediaItemsAiFields(db)
   migrateLibraryAiSettings(db)
+  migrateAiJobs(db)
   seedAppSettings(db)
 }
 
@@ -117,6 +118,7 @@ function seedAppSettings(db: Database.Database): void {
     ai_endpoint: '',
     ai_model: '',
     preferred_language: 'English',
+    ai_max_retries: '3',
   }
   const insert = db.prepare(
     'INSERT OR IGNORE INTO app_settings (key, value) VALUES (?, ?)'
@@ -298,3 +300,25 @@ function migrateLibrariesType(db: Database.Database): void {
     `)
   }
 }
+
+function migrateAiJobs(db: Database.Database): void {
+  db.exec(`
+    CREATE TABLE IF NOT EXISTS ai_jobs (
+      id           TEXT PRIMARY KEY,
+      item_key     TEXT NOT NULL,
+      library_id   TEXT NOT NULL,
+      job_type     TEXT NOT NULL CHECK(job_type IN ('tag','describe','extract','translate')),
+      status       TEXT NOT NULL DEFAULT 'queued' CHECK(status IN ('queued','running','completed','failed')),
+      error        TEXT,
+      attempt      INTEGER NOT NULL DEFAULT 0,
+      max_retries  INTEGER NOT NULL DEFAULT 3,
+      created_at   INTEGER NOT NULL,
+      started_at   INTEGER,
+      completed_at INTEGER,
+      item_title   TEXT
+    );
+
+    CREATE INDEX IF NOT EXISTS ai_jobs_status ON ai_jobs(status);
+    CREATE INDEX IF NOT EXISTS ai_jobs_created_at ON ai_jobs(created_at);
+  `)
+}