diff --git a/src/main/db/interruptedIndexing.ts b/src/main/db/interruptedIndexing.ts
new file mode 100644
index 0000000..9297992
--- /dev/null
+++ b/src/main/db/interruptedIndexing.ts
@@ -0,0 +1,23 @@
+export const INTERRUPTED_INDEXING_ERROR =
+  'Indexing was interrupted because KnowNote exited. Retry indexing to continue.'
+
+interface RecoveryDatabase {
+  prepare(sql: string): {
+    run(error: string, updatedAt: number): { changes: number | bigint }
+  }
+}
+
+/** Run only at desktop startup, before any ingestion jobs or folder watchers start. */
+export function markInterruptedIndexingFailed(
+  database: RecoveryDatabase,
+  now = new Date()
+): number {
+  const result = database
+    .prepare(
+      `UPDATE documents
+       SET status = 'failed', error_message = ?, updated_at = ?
+       WHERE status IN ('pending', 'processing')`
+    )
+    .run(INTERRUPTED_INDEXING_ERROR, Math.floor(now.getTime() / 1000))
+  return Number(result.changes)
+}
diff --git a/src/main/index.ts b/src/main/index.ts
index c3b1497..cb352ba 100644
--- a/src/main/index.ts
+++ b/src/main/index.ts
@@ -6,8 +6,10 @@ import {
   runMigrations,
   initVectorStore,
   closeDatabase,
-  executeCheckpoint
+  executeCheckpoint,
+  getSqlite
 } from './db'
+import { markInterruptedIndexingFailed } from './db/interruptedIndexing'
 import { ConnectionManager } from './models/ConnectionManager'
 import { EmbeddingService } from './services/EmbeddingService'
 import { SessionAutoSwitchService } from './services/SessionAutoSwitchService'
@@ -93,6 +95,14 @@ app.whenReady().then(async () => {
   Logger.info('Main', 'Initializing database...')
   initDatabase()
   runMigrations()
+  // The ingestion queue is in memory. Leftover live statuses belong to the previous
+  // process; make them retryable before folder reconciliation can enqueue new jobs.
+  const sqlite = getSqlite()
+  if (!sqlite) throw new Error('Database unavailable during indexing recovery')
+  const interrupted = markInterruptedIndexingFailed(sqlite)
+  if (interrupted > 0) {
+    Logger.info('Main', `Marked ${interrupted} interrupted indexing task(s) as failed`)
+  }
   initVectorStore()
   // The resolver is lazy on purpose: `knowledgeService` is constructed further down, and
   // the protocol only ever answers requests from a renderer that loads after startup.
diff --git a/src/renderer/src/components/notebook/anki/AnkiConfigDialog.tsx b/src/renderer/src/components/notebook/anki/AnkiConfigDialog.tsx
index 94be51e..e86b481 100644
--- a/src/renderer/src/components/notebook/anki/AnkiConfigDialog.tsx
+++ b/src/renderer/src/components/notebook/anki/AnkiConfigDialog.tsx
@@ -136,7 +136,7 @@ export default function AnkiConfigDialog({
         </div>
 
         <DialogFooter>
-          <Button variant="outline" onClick={() => onOpenChange(false)}>
+          <Button variant="outline" onClick={() => handleOpenChange(false)}>
             {t('cancel')}
           </Button>
           <Button onClick={handleGenerate}>{t('startGenerate')}</Button>
diff --git a/src/renderer/src/components/notebook/quiz/QuizStartDialog.tsx b/src/renderer/src/components/notebook/quiz/QuizStartDialog.tsx
index fd41f02..867c5a3 100644
--- a/src/renderer/src/components/notebook/quiz/QuizStartDialog.tsx
+++ b/src/renderer/src/components/notebook/quiz/QuizStartDialog.tsx
@@ -131,7 +131,7 @@ export default function QuizStartDialog({
         </div>
 
         <DialogFooter>
-          <Button variant="outline" onClick={onClose}>
+          <Button variant="outline" onClick={() => handleOpenChange(false)}>
             {t('cancel')}
           </Button>
           <Button onClick={handleStart} disabled={!canStart}>
diff --git a/test/interruptedIndexing.test.ts b/test/interruptedIndexing.test.ts
new file mode 100644
index 0000000..64388f7
--- /dev/null
+++ b/test/interruptedIndexing.test.ts
@@ -0,0 +1,65 @@
+import { test } from 'node:test'
+import assert from 'node:assert/strict'
+import { DatabaseSync } from 'node:sqlite'
+import { readFileSync } from 'node:fs'
+import {
+  INTERRUPTED_INDEXING_ERROR,
+  markInterruptedIndexingFailed
+} from '../src/main/db/interruptedIndexing.ts'
+
+test('startup recovery makes interrupted indexing retryable without touching finished sources', () => {
+  const db = new DatabaseSync(':memory:')
+  try {
+    db.exec(`CREATE TABLE documents (
+      id TEXT PRIMARY KEY, status TEXT, error_message TEXT, updated_at INTEGER,
+      content TEXT, local_file_path TEXT, chunk_count INTEGER
+    )`)
+    const insert = db.prepare('INSERT INTO documents VALUES (?, ?, ?, ?, ?, ?, ?)')
+    for (const status of ['pending', 'processing', 'indexed', 'failed']) {
+      insert.run(
+        status,
+        status,
+        status === 'failed' ? 'Original failure' : null,
+        100,
+        'Saved content',
+        '/saved/source.pdf',
+        3
+      )
+    }
+    const now = new Date('2026-01-01T00:00:00Z')
+    assert.equal(markInterruptedIndexingFailed(db, now), 2)
+    const rows = db.prepare('SELECT * FROM documents ORDER BY id').all()
+    for (const row of rows) {
+      assert.equal(row.content, 'Saved content')
+      assert.equal(row.local_file_path, '/saved/source.pdf')
+      assert.equal(row.chunk_count, 3)
+      if (row.id === 'pending' || row.id === 'processing') {
+        assert.equal(row.status, 'failed')
+        assert.equal(row.error_message, INTERRUPTED_INDEXING_ERROR)
+        assert.equal(row.updated_at, now.getTime() / 1000)
+      } else {
+        assert.equal(row.status, row.id)
+        assert.equal(row.updated_at, 100)
+        assert.equal(row.error_message, row.id === 'failed' ? 'Original failure' : null)
+      }
+    }
+    assert.equal(markInterruptedIndexingFailed(db, new Date()), 0)
+  } finally {
+    db.close()
+  }
+})
+
+test('recovery runs after migrations and before new ingestion can start', () => {
+  const source = readFileSync('src/main/index.ts', 'utf8')
+  const recovery = source.indexOf('markInterruptedIndexingFailed(sqlite)')
+  assert.ok(recovery > source.indexOf('  runMigrations()'))
+  assert.ok(recovery < source.indexOf('new KnowledgeService('))
+  assert.ok(recovery < source.indexOf('await knowledgeService.reconcileWatchedFolders()'))
+})
+
+test('Quiz and Anki Cancel buttons use the same reset path as dismissing the dialog', () => {
+  for (const path of ['quiz/QuizStartDialog', 'anki/AnkiConfigDialog']) {
+    const source = readFileSync(`src/renderer/src/components/notebook/${path}.tsx`, 'utf8')
+    assert.match(source, /variant="outline" onClick=\{\(\) => handleOpenChange\(false\)\}/)
+  }
+})