diff --git a/nanoclaude/services/worker.py b/nanoclaude/services/worker.py
index 1f1fcb0..8c02416 100644
--- a/nanoclaude/services/worker.py
+++ b/nanoclaude/services/worker.py
@@ -368,7 +368,7 @@ async def run(job: Job) -> None:
                     notice = "서고를 확인하는 중입니다..."
                     await send_to_synology(notice, raw=True)
 
-                # 일반 도구 실행 (document.ask는 긴 timeout)
+                # 일반 도구 실행 (document.ask는 긴 timeout + 중간 안내)
                 timeout = DOCUMENT_ASK_TIMEOUT if (tool_name == "document" and operation == "ask") else TOOL_TIMEOUT
                 doc_start = time()
                 if tool_name == "document":
@@ -377,10 +377,28 @@ async def run(job: Job) -> None:
                                 any(k in job.message.lower() for k in ["산업안전", "위험성평가", "asme", "법령"]),
                                 any(s in job.message.lower() for s in ["목록", "리스트", "제목만"]),
                                 params.get("query", "")[:50])
-                try:
-                    result = await asyncio.wait_for(execute_tool(tool_name, operation, params), timeout=timeout)
-                except asyncio.TimeoutError:
-                    result = {"ok": False, "tool": tool_name, "operation": operation, "data": [], "summary": "", "error": "⚠️ 서비스 응답 시간이 초과되었습니다."}
+
+                # document.ask는 Gemma 분석으로 오래 걸림 → 10초 후 중간 안내
+                if tool_name == "document" and operation == "ask" and job.callback == "synology":
+                    tool_task = asyncio.create_task(
+                        asyncio.wait_for(execute_tool(tool_name, operation, params), timeout=timeout)
+                    )
+                    analyze_notice_sent = False
+                    while not tool_task.done():
+                        await asyncio.sleep(2)
+                        if not tool_task.done() and not analyze_notice_sent and (time() - doc_start) >= 10:
+                            await send_to_synology("자료를 분석하고 있습니다...", raw=True)
+                            analyze_notice_sent = True
+                    try:
+                        result = tool_task.result()
+                    except asyncio.TimeoutError:
+                        result = {"ok": False, "tool": tool_name, "operation": operation, "data": [], "summary": "", "error": "⚠️ 서비스 응답 시간이 초과되었습니다."}
+                else:
+                    try:
+                        result = await asyncio.wait_for(execute_tool(tool_name, operation, params), timeout=timeout)
+                    except asyncio.TimeoutError:
+                        result = {"ok": False, "tool": tool_name, "operation": operation, "data": [], "summary": "", "error": "⚠️ 서비스 응답 시간이 초과되었습니다."}
+
                 if tool_name == "document":
                     logger.info("Job %s document.%s ok=%s elapsed=%.1fs", job.id, operation, result.get("ok"), time() - doc_start)