diff --git a/src/resources/extensions/gsd/gsd-db.ts b/src/resources/extensions/gsd/gsd-db.ts
index 1559b8616..617eab0fb 100644
--- a/src/resources/extensions/gsd/gsd-db.ts
+++ b/src/resources/extensions/gsd/gsd-db.ts
@@ -778,8 +778,21 @@ export function openDatabase(path: string): boolean {
   try {
     initSchema(adapter, fileBacked);
   } catch (err) {
-    try { adapter.close(); } catch { /* swallow */ }
-    throw err;
+    // Corrupt freelist: DDL fails with "malformed" but VACUUM can rebuild.
+    // Attempt VACUUM recovery before giving up (see #2519).
+    if (fileBacked && err instanceof Error && err.message?.includes("malformed")) {
+      try {
+        adapter.exec("VACUUM");
+        initSchema(adapter, fileBacked);
+        process.stderr.write("gsd-db: recovered corrupt database via VACUUM\n");
+      } catch (retryErr) {
+        try { adapter.close(); } catch { /* swallow */ }
+        throw retryErr;
+      }
+    } else {
+      try { adapter.close(); } catch { /* swallow */ }
+      throw err;
+    }
   }
 
   currentDb = adapter;
diff --git a/src/resources/extensions/gsd/tests/vacuum-recovery.test.ts b/src/resources/extensions/gsd/tests/vacuum-recovery.test.ts
new file mode 100644
index 000000000..5cd0bb230
--- /dev/null
+++ b/src/resources/extensions/gsd/tests/vacuum-recovery.test.ts
@@ -0,0 +1,154 @@
+import { describe, test } from 'node:test';
+import assert from 'node:assert/strict';
+import * as fs from 'node:fs';
+import * as path from 'node:path';
+import * as os from 'node:os';
+import { createRequire } from 'node:module';
+import {
+  openDatabase,
+  closeDatabase,
+  isDbAvailable,
+  _getAdapter,
+} from '../gsd-db.ts';
+
+const _require = createRequire(import.meta.url);
+
+// ═══════════════════════════════════════════════════════════════════════════
+// Helpers
+// ═══════════════════════════════════════════════════════════════════════════
+
+function tempDbPath(): string {
+  const dir = fs.mkdtempSync(path.join(os.tmpdir(), 'gsd-vacuum-test-'));
+  return path.join(dir, 'test.db');
+}
+
+function cleanup(dbPath: string): void {
+  closeDatabase();
+  try {
+    const dir = path.dirname(dbPath);
+    for (const f of fs.readdirSync(dir)) {
+      fs.unlinkSync(path.join(dir, f));
+    }
+    fs.rmdirSync(dir);
+  } catch { /* best effort */ }
+}
+
+/**
+ * Create a SQLite DB with a corrupt freelist that causes DDL to fail
+ * with "database disk image is malformed" but is recoverable via VACUUM.
+ *
+ * Strategy:
+ * 1. Create a DB with schema_version at v0 (so initSchema needs to run DDL)
+ * 2. Add padding rows to create many pages, then delete + drop to free them
+ * 3. Corrupt the freelist trunk pointer to point at a B-tree page
+ *
+ * This simulates the real-world scenario described in #2519: an interrupted
+ * WAL checkpoint leaves the freelist in an inconsistent state.
+ */
+function createCorruptFreelistDb(dbPath: string): void {
+  // Use node:sqlite directly to build the minimal corrupt DB
+  const sqlite = _require('node:sqlite');
+  const db = new sqlite.DatabaseSync(dbPath);
+  db.exec('PRAGMA journal_mode=WAL');
+  db.exec('CREATE TABLE schema_version (version INTEGER NOT NULL, applied_at TEXT NOT NULL)');
+  db.exec("INSERT INTO schema_version VALUES (0, '2024-01-01')");
+  // Pad with data to create many pages, then free them
+  db.exec('CREATE TABLE _padding (id INTEGER PRIMARY KEY, data TEXT)');
+  for (let i = 0; i < 30; i++) {
+    db.exec(`INSERT INTO _padding (data) VALUES ('${'x'.repeat(4000)}')`);
+  }
+  db.exec('DELETE FROM _padding');
+  db.exec('DROP TABLE _padding');
+  db.exec('PRAGMA wal_checkpoint(TRUNCATE)');
+  db.close();
+
+  // Remove WAL/SHM files to ensure clean file-only state
+  try { fs.unlinkSync(dbPath + '-wal'); } catch { /* may not exist */ }
+  try { fs.unlinkSync(dbPath + '-shm'); } catch { /* may not exist */ }
+
+  // Corrupt: point freelist trunk (offset 32-35) to page 2 (a B-tree page),
+  // and claim 10 free pages (offset 36-39)
+  const fd = fs.openSync(dbPath, 'r+');
+  try {
+    const buf = Buffer.alloc(8);
+    buf.writeUInt32BE(2, 0);   // trunk page = page 2 (actually a B-tree page)
+    buf.writeUInt32BE(10, 4);  // freelist count = 10
+    fs.writeSync(fd, buf, 0, 8, 32);
+  } finally {
+    fs.closeSync(fd);
+  }
+}
+
+// ═══════════════════════════════════════════════════════════════════════════
+// Tests
+// ═══════════════════════════════════════════════════════════════════════════
+
+describe('openDatabase VACUUM recovery on corrupt freelist', () => {
+
+  test('recovers a file-backed DB with corrupt freelist via VACUUM', () => {
+    const dbPath = tempDbPath();
+
+    // Create a DB with corrupt freelist (schema at v0 so initSchema runs DDL)
+    createCorruptFreelistDb(dbPath);
+
+    // Without the fix, this throws "database disk image is malformed".
+    // With the fix, openDatabase detects "malformed", runs VACUUM, retries.
+    const ok = openDatabase(dbPath);
+    assert.ok(ok, 'openDatabase should succeed after VACUUM recovery');
+    assert.ok(isDbAvailable(), 'DB should be available after recovery');
+
+    // Verify full schema was applied
+    const adapter = _getAdapter()!;
+    const row = adapter.prepare(
+      'SELECT MAX(version) as version FROM schema_version',
+    ).get();
+    assert.ok(
+      typeof row?.['version'] === 'number' && (row['version'] as number) > 0,
+      'schema_version should have a positive version after recovery',
+    );
+
+    cleanup(dbPath);
+  });
+
+  test('does not attempt VACUUM for non-malformed errors', () => {
+    // openDatabase with :memory: never hits the fileBacked VACUUM path,
+    // so non-malformed errors propagate directly. We verify by checking
+    // that a non-file error from an in-memory DB propagates unchanged.
+    // (In-memory DBs always succeed for initSchema, so this is a design
+    // check — the VACUUM path is only for fileBacked = true.)
+    const ok = openDatabase(':memory:');
+    assert.ok(ok, 'in-memory DB should open fine');
+    closeDatabase();
+  });
+
+  test('throws if VACUUM itself fails on unrecoverable corruption', () => {
+    const dbPath = tempDbPath();
+
+    // Create a file with valid SQLite header but thoroughly corrupt content
+    const page = Buffer.alloc(4096);
+    // SQLite magic: "SQLite format 3\0"
+    page.write('SQLite format 3\0', 0, 'utf8');
+    // Page size: 4096 (big-endian at offset 16)
+    page.writeUInt16BE(4096, 16);
+    page[18] = 1;  // write version
+    page[19] = 1;  // read version
+    page[20] = 0;  // reserved space
+    page[21] = 64; // max embedded payload fraction
+    page[22] = 32; // min embedded payload fraction
+    page[23] = 32; // leaf payload fraction
+    page.writeUInt32BE(1, 28);   // page_count = 1
+    page.writeUInt32BE(999, 32); // corrupt freelist trunk
+    page.writeUInt32BE(5, 36);   // freelist count = 5
+
+    fs.writeFileSync(dbPath, page);
+
+    // Should throw — VACUUM cannot save a thoroughly corrupt file
+    assert.throws(
+      () => openDatabase(dbPath),
+      /./,
+      'should throw for unrecoverable corruption',
+    );
+
+    cleanup(dbPath);
+  });
+});