diff --git a/src/acp/connection.py b/src/acp/connection.py
index 84d009cf..013fd538 100644
--- a/src/acp/connection.py
+++ b/src/acp/connection.py
@@ -283,6 +283,16 @@ async def _execute_request(self, message: dict[str, Any]) -> dict[str, Any]:
                 except Exception:
                     data = {"details": str(exc)}
                 payload["error"] = RequestError.internal_error(data).to_error_obj()
+            # One gate for every payload shape. The response is already attributed to a
+            # request id, and ``json.dumps`` is what each transport calls, so anything it
+            # refuses here would otherwise strand the peer inside ``transport.send``, where
+            # the failure escapes the response task with no handler left to answer.
+            try:
+                json.dumps(payload)
+            except Exception as exc:
+                logging.exception("Response for method=%s could not be encoded", method, exc_info=exc)
+                payload.pop("result", None)
+                payload["error"] = RequestError.internal_error({"details": str(exc)}).to_error_obj()
         return payload
 
     async def _run_notification(self, message: dict[str, Any]) -> None:
diff --git a/tests/test_rpc.py b/tests/test_rpc.py
index 43c37fd1..0a8a843a 100644
--- a/tests/test_rpc.py
+++ b/tests/test_rpc.py
@@ -975,3 +975,74 @@ async def test_connection_init_under_eager_task_factory(server):
     await asyncio.sleep(0)
     assert conn._disconnected is False
     await conn.close()
+
+
+@pytest.mark.asyncio
+async def test_unserialisable_raw_result_answers_the_peer(server):
+    # Regression: a handler returning a raw (non-BaseModel) value that json.dumps cannot
+    # encode used to build a payload that died in the transport, so no response line was
+    # ever written and the peer waited on the request id forever.
+    async def handler(method: str, params: Any, is_notification: bool) -> Any:
+        return {"x": {1, 2}}
+
+    conn = Connection(handler, server.client_writer, server.client_reader)
+
+    req = {"jsonrpc": "2.0", "id": 1, "method": "custom/thing", "params": {}}
+    server.server_writer.write((json.dumps(req) + "\n").encode())
+    await server.server_writer.drain()
+
+    line = await asyncio.wait_for(server.server_reader.readline(), timeout=1)
+    resp = json.loads(line)
+    assert resp["id"] == 1
+    assert resp["error"]["code"] == -32603
+    details = resp["error"]["data"]["details"]
+    assert "set" in details and "JSON serializable" in details
+
+    await conn.close()
+
+
+@pytest.mark.asyncio
+async def test_base_model_result_with_a_set_is_coerced_and_still_answers(server):
+    # Pins why the BaseModel branch above needs no representability check:
+    # model_dump(mode="json") already coerces an Any-typed set into a list. If that ever
+    # stops being true, this test says so instead of the check silently becoming too narrow.
+    async def handler(method: str, params: Any, is_notification: bool) -> Any:
+        return AuthenticateResponse(field_meta={"tags": {1, 2}})
+
+    conn = Connection(handler, server.client_writer, server.client_reader)
+
+    req = {"jsonrpc": "2.0", "id": 2, "method": "authenticate", "params": {}}
+    server.server_writer.write((json.dumps(req) + "\n").encode())
+    await server.server_writer.drain()
+
+    line = await asyncio.wait_for(server.server_reader.readline(), timeout=1)
+    resp = json.loads(line)
+    assert resp["id"] == 2
+    assert "error" not in resp
+    assert sorted(resp["result"]["_meta"]["tags"]) == [1, 2]
+
+    await conn.close()
+
+
+@pytest.mark.asyncio
+async def test_unserialisable_request_error_data_answers_the_peer(server):
+    # Regression: ``RequestError.data`` is typed ``Any``, so a handler raising a structured
+    # protocol error whose data json.dumps cannot encode used to build a payload that died in
+    # the transport, leaving no response line and the peer waiting on the request id forever.
+    async def handler(method: str, params: Any, is_notification: bool) -> Any:
+        raise RequestError(-32000, "boom", data={"x": {1, 2}})
+
+    conn = Connection(handler, server.client_writer, server.client_reader)
+
+    req = {"jsonrpc": "2.0", "id": 3, "method": "custom/thing", "params": {}}
+    server.server_writer.write((json.dumps(req) + "\n").encode())
+    await server.server_writer.drain()
+
+    line = await asyncio.wait_for(server.server_reader.readline(), timeout=1)
+    resp = json.loads(line)
+    assert resp["id"] == 3
+    assert resp["error"]["code"] == -32603
+    details = resp["error"]["data"]["details"]
+    assert "set" in details and "JSON serializable" in details
+
+    await conn.close()