diff --git a/workspace/a2a_mcp_server.py b/workspace/a2a_mcp_server.py
index 0bf2d095..f15a2777 100644
--- a/workspace/a2a_mcp_server.py
+++ b/workspace/a2a_mcp_server.py
@@ -16,6 +16,7 @@ import asyncio
 import json
 import logging
 import os
+import stat
 import sys
 from typing import Callable
 
@@ -444,6 +445,52 @@ def _build_channel_notification(msg: dict) -> dict:
 
 # --- MCP Server (JSON-RPC over stdio) ---
 
+
+def _assert_stdio_is_pipe_compatible(
+    stdin_fd: int = 0, stdout_fd: int = 1
+) -> None:
+    """Fail fast with a friendly message when stdio isn't pipe-compatible.
+
+    asyncio.connect_read_pipe / connect_write_pipe accept only pipes,
+    sockets, and character devices. When molecule-mcp is launched with
+    stdout redirected to a regular file (CI smoke tests, ad-hoc local
+    debugging that captures output), the asyncio call later raises
+    ``ValueError: Pipe transport is only for pipes, sockets and character
+    devices`` from inside the event loop — surfaced to the operator as a
+    confusing traceback. Detect early and exit cleanly with guidance
+    instead. See molecule-ai-workspace-runtime#61.
+    """
+    for name, fd in (("stdin", stdin_fd), ("stdout", stdout_fd)):
+        try:
+            mode = os.fstat(fd).st_mode
+        except OSError as exc:
+            print(
+                f"molecule-mcp: cannot stat {name} (fd={fd}): {exc}.\n"
+                f"  This MCP server expects bidirectional pipe stdio. Launch it from\n"
+                f"  an MCP-aware client (Claude Code, Cursor, etc.) — not detached\n"
+                f"  from a terminal or with stdio closed.",
+                file=sys.stderr,
+            )
+            sys.exit(2)
+        if not (
+            stat.S_ISFIFO(mode) or stat.S_ISSOCK(mode) or stat.S_ISCHR(mode)
+        ):
+            print(
+                f"molecule-mcp: {name} (fd={fd}) is a regular file, not a pipe,\n"
+                f"  socket, or character device — asyncio's stdio transport rejects\n"
+                f"  it with `ValueError: Pipe transport is only for pipes, sockets\n"
+                f"  and character devices`. Common causes:\n"
+                f"      molecule-mcp > out.txt           # stdout → regular file (fails)\n"
+                f"      molecule-mcp < input.json        # stdin  → regular file (fails)\n"
+                f"  Launch molecule-mcp from an MCP-aware client (Claude Code, Cursor,\n"
+                f"  hermes, OpenCode, etc.) so stdio is wired to a pipe pair, or use\n"
+                f"  `tee`/process substitution if you need to capture output:\n"
+                f"      molecule-mcp 2>&1 | tee out.txt  # stdout stays a pipe",
+                file=sys.stderr,
+            )
+            sys.exit(2)
+
+
 async def main():  # pragma: no cover
     """Run MCP server on stdio — reads JSON-RPC requests, writes responses."""
     reader = asyncio.StreamReader()
@@ -547,6 +594,7 @@ def cli_main() -> None:  # pragma: no cover
     break every external-runtime operator's MCP install — the 0.1.16
     ``main_sync`` rename incident is the cautionary precedent.
     """
+    _assert_stdio_is_pipe_compatible()
     asyncio.run(main())
 
 
diff --git a/workspace/tests/test_a2a_mcp_server.py b/workspace/tests/test_a2a_mcp_server.py
index 85b14dd1..6d3799fc 100644
--- a/workspace/tests/test_a2a_mcp_server.py
+++ b/workspace/tests/test_a2a_mcp_server.py
@@ -2,6 +2,7 @@
 
 import asyncio
 import json
+import os
 
 from unittest.mock import AsyncMock, MagicMock, patch
 
@@ -1071,6 +1072,104 @@ def test_inbox_bridge_swallows_closed_loop_runtime_error():
     })
 
 
+class TestStdioPipeAssertion:
+    """Pin _assert_stdio_is_pipe_compatible — the friendly fail-fast guard
+    that turns asyncio's `ValueError: Pipe transport is only for pipes,
+    sockets and character devices` into a clear operator message + exit 2.
+    See molecule-ai-workspace-runtime#61.
+    """
+
+    def test_pipe_pair_passes_silently(self):
+        """Happy path — both fds are pipes (the production launch shape
+        from any MCP client). Should return None without printing or
+        exiting."""
+        from a2a_mcp_server import _assert_stdio_is_pipe_compatible
+
+        r, w = os.pipe()
+        try:
+            # No exit, no stderr noise. We don't capture stderr here
+            # because pipe path should produce zero output.
+            _assert_stdio_is_pipe_compatible(stdin_fd=r, stdout_fd=w)
+        finally:
+            os.close(r)
+            os.close(w)
+
+    def test_regular_file_stdout_exits_with_friendly_message(
+        self, tmp_path, capsys
+    ):
+        """Reproducer for runtime#61: stdout redirected to a regular file.
+        Pre-fix this would surface upstream as
+        `ValueError: Pipe transport is only for pipes...`. Post-fix we
+        exit with code 2 and a stderr message that names the symptom +
+        fix."""
+        from a2a_mcp_server import _assert_stdio_is_pipe_compatible
+
+        # stdin = pipe (so we isolate the stdout failure path);
+        # stdout = regular file (the bug condition).
+        r, _w = os.pipe()
+        regular = tmp_path / "captured.log"
+        f = open(regular, "wb")
+        try:
+            with pytest.raises(SystemExit) as excinfo:
+                _assert_stdio_is_pipe_compatible(
+                    stdin_fd=r, stdout_fd=f.fileno()
+                )
+            assert excinfo.value.code == 2
+            err = capsys.readouterr().err
+            # Names the failing stream + the asyncio constraint that
+            # would otherwise crash. Don't pin the exact wording — the
+            # asserts pin the operator-recoverable signal only.
+            assert "stdout" in err
+            assert "regular file" in err
+            assert "pipe" in err
+        finally:
+            f.close()
+            os.close(r)
+
+    def test_regular_file_stdin_exits_with_friendly_message(
+        self, tmp_path, capsys
+    ):
+        """Symmetric case — stdin redirected from a regular file. Same
+        asyncio constraint applies via connect_read_pipe."""
+        from a2a_mcp_server import _assert_stdio_is_pipe_compatible
+
+        regular = tmp_path / "input.json"
+        regular.write_bytes(b'{"jsonrpc":"2.0","id":1,"method":"initialize"}\n')
+        f = open(regular, "rb")
+        _r, w = os.pipe()
+        try:
+            with pytest.raises(SystemExit) as excinfo:
+                _assert_stdio_is_pipe_compatible(
+                    stdin_fd=f.fileno(), stdout_fd=w
+                )
+            assert excinfo.value.code == 2
+            err = capsys.readouterr().err
+            assert "stdin" in err
+            assert "regular file" in err
+        finally:
+            f.close()
+            os.close(w)
+
+    def test_closed_fd_exits_with_stat_error(self, capsys):
+        """If stdio is closed (rare but seen in detached daemonized
+        contexts), os.fstat raises OSError. We catch it and exit 2 with
+        a guidance message instead of letting the traceback escape."""
+        from a2a_mcp_server import _assert_stdio_is_pipe_compatible
+
+        r, w = os.pipe()
+        os.close(w)  # Now `w` is a stale fd — fstat will fail.
+        try:
+            with pytest.raises(SystemExit) as excinfo:
+                _assert_stdio_is_pipe_compatible(
+                    stdin_fd=r, stdout_fd=w
+                )
+            assert excinfo.value.code == 2
+            err = capsys.readouterr().err
+            assert "cannot stat stdout" in err
+        finally:
+            os.close(r)
+
+
 def _readable(fd: int) -> bool:
     """True iff ``fd`` has bytes available without blocking. Lets
     us poll the pipe in a loop without the test hanging when the