diff --git a/lib/app/app_controller_desktop_runtime_helpers.dart b/lib/app/app_controller_desktop_runtime_helpers.dart
index 9e101e6b..f7ce4baa 100644
--- a/lib/app/app_controller_desktop_runtime_helpers.dart
+++ b/lib/app/app_controller_desktop_runtime_helpers.dart
@@ -792,7 +792,17 @@ extension AppControllerDesktopRuntimeHelpers on AppController {
       }
       final bytes = bytesResult.bytes;
       if (bytes == null) {
-        skippedArtifact = true;
+        final existingArtifactPaths =
+            await _existingWorkspaceArtifactPathsInternal(root, relativePath);
+        if (existingArtifactPaths.isEmpty) {
+          skippedArtifact = true;
+          continue;
+        }
+        wroteArtifact = true;
+        _appendArtifactRelativePathsInternal(
+          currentTaskArtifactRelativePaths,
+          existingArtifactPaths,
+        );
         continue;
       }
       final target = await _nextArtifactTargetFileInternal(root, relativePath);
@@ -813,7 +823,10 @@ extension AppControllerDesktopRuntimeHelpers on AppController {
             target.path,
           );
       if (writtenRelativePath != null && writtenRelativePath.isNotEmpty) {
-        currentTaskArtifactRelativePaths.add(writtenRelativePath);
+        _appendArtifactRelativePathsInternal(
+          currentTaskArtifactRelativePaths,
+          <String>[writtenRelativePath],
+        );
       }
     }
 
@@ -1145,6 +1158,57 @@ extension AppControllerDesktopRuntimeHelpers on AppController {
   ) => kGatewayRemoteProfileIndex;
 }
 
+void _appendArtifactRelativePathsInternal(
+  List<String> target,
+  List<String> paths,
+) {
+  for (final path in paths) {
+    if (!target.contains(path)) {
+      target.add(path);
+    }
+  }
+}
+
+Future<List<String>> _existingWorkspaceArtifactPathsInternal(
+  Directory root,
+  String relativePath,
+) async {
+  final targetPath = DesktopThreadArtifactService.resolveAbsolutePathInternal(
+    root.path,
+    relativePath,
+  );
+  final targetType = await FileSystemEntity.type(
+    targetPath,
+    followLinks: false,
+  );
+  if (targetType == FileSystemEntityType.file) {
+    final resolvedRelativePath =
+        DesktopThreadArtifactService.relativePathInternal(
+          root.path,
+          targetPath,
+        );
+    return resolvedRelativePath == null || resolvedRelativePath.isEmpty
+        ? const <String>[]
+        : <String>[resolvedRelativePath];
+  }
+  if (targetType != FileSystemEntityType.directory) {
+    return const <String>[];
+  }
+  final files = await DesktopThreadArtifactService().collectFilesInternal(
+    Directory(targetPath),
+  );
+  final paths = <String>[];
+  for (final file in files) {
+    final resolvedRelativePath =
+        DesktopThreadArtifactService.relativePathInternal(root.path, file.path);
+    if (resolvedRelativePath != null && resolvedRelativePath.isNotEmpty) {
+      paths.add(resolvedRelativePath);
+    }
+  }
+  paths.sort();
+  return paths;
+}
+
 String _normalizeAuthorizationHeaderInternal(String raw) {
   final trimmed = raw.trim();
   if (trimmed.isEmpty) {
diff --git a/test/runtime/app_controller_thread_workspace_binding_test.dart b/test/runtime/app_controller_thread_workspace_binding_test.dart
index 3025ceea..63a67609 100644
--- a/test/runtime/app_controller_thread_workspace_binding_test.dart
+++ b/test/runtime/app_controller_thread_workspace_binding_test.dart
@@ -589,6 +589,88 @@ void main() {
     },
   );
 
+  test('syncs existing workspace directory artifacts recursively', () async {
+    final controller = AppController(
+      environmentOverride: const <String, String>{},
+    );
+    addTearDown(controller.dispose);
+
+    final localWorkspace = await Directory.systemTemp.createTemp(
+      'xworkmate-recursive-artifact-workspace-',
+    );
+    addTearDown(() async {
+      if (await localWorkspace.exists()) {
+        await localWorkspace.delete(recursive: true);
+      }
+    });
+    await Directory(
+      '${localWorkspace.path}/assets/images/chapters',
+    ).create(recursive: true);
+    await File(
+      '${localWorkspace.path}/assets/images/cover.png',
+    ).writeAsBytes(<int>[1, 2, 3]);
+    await File(
+      '${localWorkspace.path}/assets/images/chapters/chapter-1.png',
+    ).writeAsBytes(<int>[4, 5, 6]);
+    await File(
+      '${localWorkspace.path}/chapters/codex-chapter-breakdown.md',
+    ).create(recursive: true);
+
+    controller.upsertTaskThreadInternal(
+      'unit-fixture-task-a',
+      workspaceBinding: WorkspaceBinding(
+        workspaceId: 'unit-fixture-task-a',
+        workspaceKind: WorkspaceKind.localFs,
+        workspacePath: localWorkspace.path,
+        displayPath: localWorkspace.path,
+        writable: true,
+      ),
+    );
+
+    final result = GoTaskServiceResult(
+      success: true,
+      message: 'generated files',
+      turnId: 'turn-recursive',
+      raw: <String, dynamic>{
+        'artifacts': <Map<String, dynamic>>[
+          <String, dynamic>{'relativePath': 'assets/images/'},
+          <String, dynamic>{
+            'relativePath': 'chapters/codex-chapter-breakdown.md',
+          },
+        ],
+      },
+      errorMessage: '',
+      resolvedModel: '',
+      route: GoTaskServiceRoute.externalAcpSingle,
+    );
+
+    await controller.persistGoTaskArtifactsForSessionInternal(
+      'unit-fixture-task-a',
+      result,
+    );
+
+    final thread = controller.requireTaskThreadForSessionInternal(
+      'unit-fixture-task-a',
+    );
+    expect(thread.lastArtifactSyncStatus, 'synced');
+    expect(thread.lastTaskArtifactRelativePaths, <String>[
+      'assets/images/chapters/chapter-1.png',
+      'assets/images/cover.png',
+      'chapters/codex-chapter-breakdown.md',
+    ]);
+    final snapshot = await controller.loadAssistantArtifactSnapshot(
+      sessionKey: 'unit-fixture-task-a',
+    );
+    expect(
+      snapshot.resultEntries.map((entry) => entry.relativePath),
+      containsAll(<String>[
+        'assets/images/chapters/chapter-1.png',
+        'assets/images/cover.png',
+        'chapters/codex-chapter-breakdown.md',
+      ]),
+    );
+  });
+
   test(
     'downloads bridge URL artifacts into the local thread workspace',
     () async {