diff --git a/lib/app/app_controller_desktop_thread_actions.dart b/lib/app/app_controller_desktop_thread_actions.dart
index a89048c7..aa5b610c 100644
--- a/lib/app/app_controller_desktop_thread_actions.dart
+++ b/lib/app/app_controller_desktop_thread_actions.dart
@@ -461,9 +461,13 @@ extension AppControllerDesktopThreadActions on AppController {
       localAttachments,
     );
     final taskLoadClass = classifyGatewayTaskLoadInternal(message);
+    final expectedArtifactExtensions =
+        expectedGatewayArtifactExtensionsInternal(message);
     final taskMetadata = Map<String, dynamic>.unmodifiable(<String, dynamic>{
       ...dispatch.metadata,
       'taskLoadClass': taskLoadClass,
+      if (expectedArtifactExtensions.isNotEmpty)
+        'expectedArtifactExtensions': expectedArtifactExtensions,
     });
     final executionWorkingDirectory = gatewayExecutionWorkingDirectoryInternal(
       target: currentTarget,
@@ -764,6 +768,42 @@ extension AppControllerDesktopThreadActions on AppController {
     return 'short_task';
   }
 
+  List<String> expectedGatewayArtifactExtensionsInternal(String requestText) {
+    final normalized = requestText.trim().toLowerCase();
+    final result = <String>[];
+
+    void add(String value) {
+      final normalizedValue = value.trim().toLowerCase().replaceFirst(
+        RegExp(r'^\.'),
+        '',
+      );
+      if (normalizedValue.isEmpty || result.contains(normalizedValue)) {
+        return;
+      }
+      result.add(normalizedValue);
+    }
+
+    for (final match in RegExp(
+      r'\.([a-z0-9]{2,5})\b',
+      caseSensitive: false,
+    ).allMatches(normalized)) {
+      add(match.group(1) ?? '');
+    }
+    for (final match in RegExp(
+      r'\b([a-z0-9]{2,5})\s*(?:格式|文件|产物|artifact|file|output)',
+      caseSensitive: false,
+    ).allMatches(normalized)) {
+      add(match.group(1) ?? '');
+    }
+    for (final match in RegExp(
+      r'(?:输出|导出|生成|制作)\s*([a-z0-9]{2,5})',
+      caseSensitive: false,
+    ).allMatches(normalized)) {
+      add(match.group(1) ?? '');
+    }
+    return List<String>.unmodifiable(result);
+  }
+
   bool usesOpenClawGatewayQueueInternal(
     AssistantExecutionTarget target,
     SingleAgentProvider provider,
diff --git a/pubspec.yaml b/pubspec.yaml
index 134073bb..440a1cb7 100644
--- a/pubspec.yaml
+++ b/pubspec.yaml
@@ -2,9 +2,9 @@ name: xworkmate
 description: "XWorkmate desktop-first AI workspace shell."
 publish_to: 'none'
 
-version: 1.1.3+1
-build-date: 2026-05-28
-build-id: 82d46f5
+version: 1.1.4
+build-date: 2026-05-30
+build-id: 94405c9
 
 environment:
   sdk: ^3.11.0
diff --git a/test/runtime/assistant_execution_target_test.dart b/test/runtime/assistant_execution_target_test.dart
index 452cd17a..6668fc6d 100644
--- a/test/runtime/assistant_execution_target_test.dart
+++ b/test/runtime/assistant_execution_target_test.dart
@@ -1186,6 +1186,31 @@ void main() {
       },
     );
 
+    test(
+      'sendChatMessage declares expected artifacts for complex PDF chains',
+      () async {
+        final fakeGoTaskService = _RecordingGoTaskServiceClient();
+        final controller = _connectedGatewayController(fakeGoTaskService);
+        addTearDown(controller.dispose);
+
+        await controller.ensureActiveAssistantThreadInternal();
+        await controller.setAssistantExecutionTarget(
+          AssistantExecutionTarget.gateway,
+        );
+        await controller.sendChatMessage(
+          '围绕\n\n'
+          '从单机权限 → 网络边界 → Web安全 → 云身份 → Zero Trust → AI Agent 身份 → AI模型与知识保护 演进 800-1500字\n'
+          '拆章节 -> 每章调用 Codex -> 每章 GPT images2 生成图 -> 汇总排版 ->\n\n'
+          '最后 输出 PDF文件',
+        );
+
+        expect(fakeGoTaskService.requests, hasLength(1));
+        final request = fakeGoTaskService.requests.single;
+        expect(request.metadata['taskLoadClass'], 'complex_long_chain_task');
+        expect(request.metadata['expectedArtifactExtensions'], <String>['pdf']);
+      },
+    );
+
     test(
       'sendChatMessage classifies simple Gateway prompts as short tasks',
       () async {