diff --git a/agent/deep_assistant.py b/agent/deep_assistant.py
index ad1533d..45276f4 100644
--- a/agent/deep_assistant.py
+++ b/agent/deep_assistant.py
@@ -23,6 +23,7 @@ from .guideline_middleware import GuidelineMiddleware
 from .tool_output_length_middleware import ToolOutputLengthMiddleware
 from .tool_use_cleanup_middleware import ToolUseCleanupMiddleware
 from .tool_metrics_middleware import ToolMetricsMiddleware
+from .tool_error_recovery_middleware import ToolErrorRecoveryMiddleware
 from .filepath_fix_middleware import FilePathFixMiddleware
 from .mcp_trace_meta import patch_mcp_client_session_trace_meta
 from utils.settings import (
@@ -567,6 +568,7 @@ def create_custom_cli_agent(
         interrupt_on = _add_interrupt_on()
 
     deepagent_middleware = [
+        ToolErrorRecoveryMiddleware(),  # Outermost: turn any tool exception into a ToolMessage so the agent can recover
         TodoListMiddleware(),
         FilePathFixMiddleware(),  # Fix extra spaces in CJK file names within tool call arguments
         CustomFilesystemMiddleware(backend=composite_backend),  # Use the custom FilesystemMiddleware with full SKILL.md reading support
diff --git a/agent/tool_error_recovery_middleware.py b/agent/tool_error_recovery_middleware.py
new file mode 100644
index 0000000..f00be37
--- /dev/null
+++ b/agent/tool_error_recovery_middleware.py
@@ -0,0 +1,98 @@
+"""Outermost middleware that converts tool exceptions into ToolMessage(status="error").
+
+When a tool call raises (most commonly an MCP `ToolException` from
+`langchain_mcp_adapters`), LangGraph's default handler re-raises and breaks the
+agent stream, which in turn breaks the SSE response to the client. This
+middleware sits as the outermost wrapper around every tool call and converts any
+caught exception into a ToolMessage so the agent can keep looping and reply to
+the user in natural language about what went wrong.
+
+`asyncio.CancelledError` is intentionally not caught — task cancellation must
+propagate. Metric emission (`ToolMetricsMiddleware`) still observes the inner
+`raise` because it sits *inside* this middleware in the chain.
+"""
+
+import asyncio
+import logging
+import re
+from typing import Any, Callable
+
+from langchain.agents.middleware import AgentMiddleware
+from langchain.tools.tool_node import ToolCallRequest
+from langchain_core.messages import ToolMessage
+
+logger = logging.getLogger("app")
+
+# Matches `text="..."` (or `text='...'`) inside MCP TextContent repr. Non-greedy
+# so each TextContent in a list is captured separately.
+_TEXT_CONTENT_PATTERN = re.compile(
+    r"""TextContent\([^)]*?text=(?P<quote>['"])(?P<text>.*?)(?<!\\)(?P=quote)""",
+    re.DOTALL,
+)
+
+
+class ToolErrorRecoveryMiddleware(AgentMiddleware):
+    """Catch tool-call exceptions and return them as error ToolMessages."""
+
+    def _extract_error_text(self, error: Exception) -> str:
+        """Pull human-readable text out of an exception.
+
+        MCP `ToolException` typically wraps a list of `TextContent` objects, so
+        their string repr looks like `[TextContent(type='text', text="...", ...)]`.
+        Strip the wrapper and keep just the inner `text` fields when present;
+        otherwise fall back to `str(error)`.
+        """
+        raw = str(error)
+        matches = _TEXT_CONTENT_PATTERN.findall(raw)
+        if matches:
+            # findall returns list of tuples because of named groups; pick group 'text' (index 1).
+            return "\n".join(text for _quote, text in matches if text)
+        return raw
+
+    def _build_error_message(
+        self,
+        request: ToolCallRequest,
+        error: Exception,
+    ) -> ToolMessage:
+        tool_call = request.tool_call or {}
+        tool_name = tool_call.get("name") or "unknown_tool"
+        tool_call_id = tool_call.get("id") or ""
+
+        error_text = self._extract_error_text(error)
+        content = f"Tool '{tool_name}' failed: {error_text}"
+
+        logger.warning(
+            "Tool error recovered as ToolMessage: tool_name=%s error_type=%s",
+            tool_name,
+            type(error).__name__,
+        )
+
+        return ToolMessage(
+            content=content,
+            tool_call_id=tool_call_id,
+            name=tool_name,
+            status="error",
+        )
+
+    def wrap_tool_call(
+        self,
+        request: ToolCallRequest,
+        handler: Callable[[ToolCallRequest], Any],
+    ) -> Any:
+        try:
+            return handler(request)
+        except Exception as exc:  # noqa: BLE001 — outermost recovery
+            return self._build_error_message(request, exc)
+
+    async def awrap_tool_call(
+        self,
+        request: ToolCallRequest,
+        handler: Callable[[ToolCallRequest], Any],
+    ) -> Any:
+        try:
+            return await handler(request)
+        except asyncio.CancelledError:
+            # Cancellation must propagate so the agent task can shut down cleanly.
+            raise
+        except Exception as exc:  # noqa: BLE001 — outermost recovery
+            return self._build_error_message(request, exc)