diff --git a/hermes_cli/middleware.py b/hermes_cli/middleware.py
index 277368dffb3..8795952a2b7 100644
--- a/hermes_cli/middleware.py
+++ b/hermes_cli/middleware.py
@@ -55,6 +55,25 @@ def middleware_payload(**kwargs: Any) -> Dict[str, Any]:
     return kwargs
 
 
+def _safe_copy(payload: Any) -> Any:
+    """Deep-copy a request payload, tolerating non-deepcopyable members.
+
+    Request payloads are normally plain JSON-shaped dicts, but an LLM request
+    can occasionally carry non-deepcopyable objects (clients, callbacks, file
+    handles). A hard ``deepcopy`` failure there would otherwise abort the whole
+    request-middleware pass. Fall back to a shallow ``dict`` copy so middleware
+    still runs and the original nested objects are shared by reference rather
+    than corrupting the live payload.
+    """
+    try:
+        return deepcopy(payload)
+    except Exception as exc:  # pragma: no cover - exercised via fallback test
+        logger.debug("deepcopy failed for request payload (%s); using shallow copy", exc)
+        if isinstance(payload, dict):
+            return dict(payload)
+        return payload
+
+
 def apply_llm_request_middleware(
     request: Dict[str, Any],
     **context: Any,
@@ -72,8 +91,8 @@ def apply_llm_request_middleware(
             trace=[],
         )
 
-    original_request = deepcopy(request)
-    current_request = deepcopy(original_request)
+    original_request = _safe_copy(request)
+    current_request = _safe_copy(original_request)
     trace: List[Dict[str, Any]] = []
 
     for result in _invoke_middleware(
@@ -87,7 +106,7 @@ def apply_llm_request_middleware(
         next_request = result.get("request")
         if not isinstance(next_request, dict):
             continue
-        current_request = deepcopy(next_request)
+        current_request = _safe_copy(next_request)
         trace.append(_trace_entry(result))
 
     return RequestMiddlewareResult(
@@ -116,8 +135,8 @@ def apply_tool_request_middleware(
             trace=[],
         )
 
-    original_args = deepcopy(args)
-    current_args = deepcopy(original_args)
+    original_args = _safe_copy(args)
+    current_args = _safe_copy(original_args)
     trace: List[Dict[str, Any]] = []
 
     for result in _invoke_middleware(
@@ -132,7 +151,7 @@ def apply_tool_request_middleware(
         next_args = result.get("args")
         if not isinstance(next_args, dict):
             continue
-        current_args = deepcopy(next_args)
+        current_args = _safe_copy(next_args)
         trace.append(_trace_entry(result))
 
     return RequestMiddlewareResult(
@@ -242,6 +261,16 @@ def _run_execution_chain(
 
         def next_call(next_payload: Any = None) -> Any:
             nonlocal next_called, next_succeeded, next_result
+            # ``next_call`` is single-use per middleware frame. Calling it more
+            # than once would re-run the downstream provider/tool, so a second
+            # invocation is a contract violation rather than a retry. Surface it
+            # instead of silently executing the terminal call twice.
+            if next_called:
+                raise RuntimeError(
+                    f"Middleware '{kind}' callback "
+                    f"{getattr(callback, '__name__', repr(callback))} called "
+                    "next_call() more than once; downstream execution is single-use"
+                )
             next_called = True
             try:
                 next_result = call_at(index + 1, payload if next_payload is None else next_payload)
diff --git a/tests/hermes_cli/test_plugins.py b/tests/hermes_cli/test_plugins.py
index ddd1dab56e4..bb889450d00 100644
--- a/tests/hermes_cli/test_plugins.py
+++ b/tests/hermes_cli/test_plugins.py
@@ -272,6 +272,54 @@ class TestPluginDiscovery:
 
         assert calls == [{"command": "interrupt"}]
 
+    def test_execution_middleware_double_next_call_does_not_run_terminal_twice(self, monkeypatch):
+        calls = []
+
+        def middleware(**kwargs):
+            first = kwargs["next_call"](kwargs["args"])
+            # Deliberate misuse: a second next_call() must not re-run the
+            # downstream tool. The chain surfaces it as an error and preserves
+            # the first (successful) downstream result.
+            kwargs["next_call"](kwargs["args"])
+            return first
+
+        manager = types.SimpleNamespace(_middleware={"tool_execution": [middleware]})
+        monkeypatch.setattr("hermes_cli.plugins.get_plugin_manager", lambda: manager)
+
+        def terminal(args):
+            calls.append(args)
+            return "terminal-result"
+
+        result = run_tool_execution_middleware("terminal", {"command": "printf ok"}, terminal)
+
+        assert result == "terminal-result"
+        assert calls == [{"command": "printf ok"}]
+
+    def test_request_middleware_tolerates_non_deepcopyable_payload(self, monkeypatch):
+        import threading
+
+        recorded = {}
+
+        def middleware(**kwargs):
+            recorded["args"] = kwargs["args"]
+            return None
+
+        manager = types.SimpleNamespace(
+            _middleware={"tool_request": [middleware]},
+            invoke_middleware=lambda kind, **kwargs: [middleware(**kwargs)],
+        )
+        monkeypatch.setattr("hermes_cli.plugins.get_plugin_manager", lambda: manager)
+
+        # threading.Lock is not deepcopyable; a hard deepcopy would raise.
+        args = {"command": "noop", "lock": threading.Lock()}
+        result = apply_tool_request_middleware("terminal", args)
+
+        # Middleware ran (payload was copied via the shallow fallback) and the
+        # non-deepcopyable member is shared by reference rather than aborting.
+        assert recorded["args"]["command"] == "noop"
+        assert result.payload["command"] == "noop"
+        assert result.payload["lock"] is args["lock"]
+
     def test_discover_project_plugins(self, tmp_path, monkeypatch):
         """Plugins in ./.hermes/plugins/ are discovered."""
         project_dir = tmp_path / "project"