deer-flow/backend/tests/test_clarification_middleware.py

"""Tests for ClarificationMiddleware, focusing on options type coercion."""

import json
from types import SimpleNamespace

import pytest
from langgraph.graph.message import add_messages

from deerflow.agents.middlewares.clarification_middleware import ClarificationMiddleware


@pytest.fixture
def middleware():
    return ClarificationMiddleware()


class TestFormatClarificationMessage:
    """Tests for _format_clarification_message options handling."""

    def test_options_as_native_list(self, middleware):
        """Normal case: options is already a list."""
        args = {
            "question": "Which env?",
            "clarification_type": "approach_choice",
            "options": ["dev", "staging", "prod"],
        }
        result = middleware._format_clarification_message(args)
        assert "1. dev" in result
        assert "2. staging" in result
        assert "3. prod" in result

    def test_options_as_json_string(self, middleware):
        """Bug case (#1995): model serializes options as a JSON string."""
        args = {
            "question": "Which env?",
            "clarification_type": "approach_choice",
            "options": json.dumps(["dev", "staging", "prod"]),
        }
        result = middleware._format_clarification_message(args)
        assert "1. dev" in result
        assert "2. staging" in result
        assert "3. prod" in result
        # Must NOT contain per-character output
        assert "1. [" not in result
        assert '2. "' not in result

    def test_options_as_json_string_scalar(self, middleware):
        """JSON string decoding to a non-list scalar is treated as one option."""
        args = {
            "question": "Which env?",
            "clarification_type": "approach_choice",
            "options": json.dumps("development"),
        }
        result = middleware._format_clarification_message(args)
        assert "1. development" in result
        # Must be a single option, not per-character iteration.
        assert "2." not in result

    def test_options_as_plain_string(self, middleware):
        """Edge case: options is a non-JSON string, treated as single option."""
        args = {
            "question": "Which env?",
            "clarification_type": "approach_choice",
            "options": "just one option",
        }
        result = middleware._format_clarification_message(args)
        assert "1. just one option" in result

    def test_options_none(self, middleware):
        """Options is None — no options section rendered."""
        args = {
            "question": "Tell me more",
            "clarification_type": "missing_info",
            "options": None,
        }
        result = middleware._format_clarification_message(args)
        assert "1." not in result

    def test_options_empty_list(self, middleware):
        """Options is an empty list — no options section rendered."""
        args = {
            "question": "Tell me more",
            "clarification_type": "missing_info",
            "options": [],
        }
        result = middleware._format_clarification_message(args)
        assert "1." not in result

    def test_options_missing(self, middleware):
        """Options key is absent — defaults to empty list."""
        args = {
            "question": "Tell me more",
            "clarification_type": "missing_info",
        }
        result = middleware._format_clarification_message(args)
        assert "1." not in result

    def test_context_included(self, middleware):
        """Context is rendered before the question."""
        args = {
            "question": "Which env?",
            "clarification_type": "approach_choice",
            "context": "Need target env for config",
            "options": ["dev", "prod"],
        }
        result = middleware._format_clarification_message(args)
        assert "Need target env for config" in result
        assert "Which env?" in result
        assert "1. dev" in result

    def test_json_string_with_mixed_types(self, middleware):
        """JSON string containing non-string elements still works."""
        args = {
            "question": "Pick one",
            "clarification_type": "approach_choice",
            "options": json.dumps(["Option A", 2, True, None]),
        }
        result = middleware._format_clarification_message(args)
        assert "1. Option A" in result
        assert "2. 2" in result
        assert "3. True" in result
        assert "4. None" in result


class TestHumanInputPayload:
    """Tests for structured human input request payloads."""

    def test_payload_with_native_options(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Which environment should I deploy to?",
                "clarification_type": "approach_choice",
                "context": "Need the target environment for config.",
                "options": ["development", "staging", "production"],
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload == {
            "version": 1,
            "kind": "human_input_request",
            "source": "ask_clarification",
            "request_id": "clarification:call-abc",
            "tool_call_id": "call-abc",
            "clarification_type": "approach_choice",
            "question": "Which environment should I deploy to?",
            "context": "Need the target environment for config.",
            "input_mode": "choice_with_other",
            "options": [
                {"id": "option-1", "label": "development", "value": "development"},
                {"id": "option-2", "label": "staging", "value": "staging"},
                {"id": "option-3", "label": "production", "value": "production"},
            ],
        }

    def test_payload_with_json_string_options(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Pick one",
                "clarification_type": "approach_choice",
                "options": json.dumps(["Option A", 2, True, None]),
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["input_mode"] == "choice_with_other"
        assert payload["options"] == [
            {"id": "option-1", "label": "Option A", "value": "Option A"},
            {"id": "option-2", "label": "2", "value": "2"},
            {"id": "option-3", "label": "True", "value": "True"},
            {"id": "option-4", "label": "None", "value": "None"},
        ]

    def test_payload_with_plain_string_option(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Pick one",
                "clarification_type": "approach_choice",
                "options": "just one option",
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["input_mode"] == "choice_with_other"
        assert payload["options"] == [{"id": "option-1", "label": "just one option", "value": "just one option"}]

    def test_payload_without_options_is_free_text(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Tell me more",
                "clarification_type": "missing_info",
                "options": None,
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["input_mode"] == "free_text"
        assert "options" not in payload

    def test_payload_missing_options_is_free_text(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Tell me more",
                "clarification_type": "missing_info",
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["input_mode"] == "free_text"
        assert "options" not in payload


class TestFormPayload:
    """v2 protocol: fields render a structured form card."""

    def _fields(self):
        return [
            {"name": "amount", "label": "Amount", "type": "number", "required": True},
            {"name": "category", "label": "Category", "type": "select", "options": ["travel", "meals"], "required": True},
            {"name": "receipts", "label": "Receipts", "type": "multi_select", "options": ["A-1", "A-2"]},
            {"name": "note", "type": "textarea"},
        ]

    def test_form_payload_with_native_fields(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Please provide the expense details.",
                "clarification_type": "missing_info",
                "fields": self._fields(),
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["version"] == 2
        assert payload["input_mode"] == "form"
        assert payload["fields"] == [
            {"name": "amount", "label": "Amount", "type": "number", "required": True},
            {
                "name": "category",
                "label": "Category",
                "type": "select",
                "required": True,
                "options": [
                    {"id": "category-option-1", "label": "travel", "value": "travel"},
                    {"id": "category-option-2", "label": "meals", "value": "meals"},
                ],
            },
            {
                "name": "receipts",
                "label": "Receipts",
                "type": "multi_select",
                "required": False,
                "options": [
                    {"id": "receipts-option-1", "label": "A-1", "value": "A-1"},
                    {"id": "receipts-option-2", "label": "A-2", "value": "A-2"},
                ],
            },
            {"name": "note", "label": "note", "type": "textarea", "required": False},
        ]

    def test_form_payload_with_json_string_fields(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Details please",
                "clarification_type": "missing_info",
                "fields": json.dumps([{"name": "amount", "type": "number"}]),
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["input_mode"] == "form"
        assert payload["fields"] == [{"name": "amount", "label": "amount", "type": "number", "required": False}]

    def test_form_takes_precedence_over_options(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Details please",
                "clarification_type": "missing_info",
                "fields": [{"name": "amount"}],
                "options": ["dev", "prod"],
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["input_mode"] == "form"
        assert "options" not in payload

    def test_unknown_field_type_degrades_to_text(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Details please",
                "clarification_type": "missing_info",
                "fields": [{"name": "amount", "type": "slider"}],
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["fields"][0]["type"] == "text"

    def test_select_without_options_degrades_to_text(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Details please",
                "clarification_type": "missing_info",
                "fields": [{"name": "category", "type": "select"}],
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["fields"][0]["type"] == "text"
        assert "options" not in payload["fields"][0]

    def test_any_invalid_field_entry_degrades_whole_form(self, middleware):
        """Atomic validation: a structurally broken entry must not silently
        vanish from an otherwise-rendered form — the whole form degrades."""
        for bad_entry in ["not-a-dict", {"label": "no name"}, {"name": "   "}]:
            payload = middleware._build_human_input_payload(
                {
                    "question": "Details please",
                    "clarification_type": "missing_info",
                    "fields": [bad_entry, {"name": "amount", "type": "number"}],
                    "options": ["dev", "prod"],
                },
                tool_call_id="call-abc",
                request_id="clarification:call-abc",
            )

            assert payload["version"] == 1
            assert payload["input_mode"] == "choice_with_other"
            assert "fields" not in payload

    def test_duplicate_field_names_degrade_whole_form(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Details please",
                "clarification_type": "missing_info",
                "fields": [
                    {"name": "amount", "type": "number"},
                    {"name": "amount", "type": "text"},
                ],
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["version"] == 1
        assert payload["input_mode"] == "free_text"
        assert "fields" not in payload

    def test_reserved_prototype_field_names_degrade_whole_form(self, middleware):
        """`__proto__`/`constructor`/... collide with JS Object.prototype in the
        frontend form-value store and must be rejected server-side."""
        for reserved in ["__proto__", "constructor", "toString", "hasOwnProperty"]:
            payload = middleware._build_human_input_payload(
                {
                    "question": "Details please",
                    "clarification_type": "missing_info",
                    "fields": [{"name": reserved, "type": "text"}],
                },
                tool_call_id="call-abc",
                request_id="clarification:call-abc",
            )

            assert payload["input_mode"] == "free_text", reserved
            assert "fields" not in payload

    def test_field_options_are_trimmed_deduped_and_blank_dropped(self, middleware):
        """Backend must never emit blank option labels — the frontend parser
        rejects the whole payload on them."""
        payload = middleware._build_human_input_payload(
            {
                "question": "Details please",
                "clarification_type": "missing_info",
                "fields": [{"name": "category", "type": "select", "options": [" travel ", "", "  ", "travel", "meals"]}],
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert [option["label"] for option in payload["fields"][0]["options"]] == ["travel", "meals"]

    def test_field_count_over_cap_degrades_whole_form(self, middleware):
        fields = [{"name": f"field_{i}", "type": "text"} for i in range(17)]
        payload = middleware._build_human_input_payload(
            {"question": "Details please", "clarification_type": "missing_info", "fields": fields},
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["input_mode"] == "free_text"
        assert "fields" not in payload

    def test_option_count_over_cap_degrades_whole_form(self, middleware):
        options = [f"option-{i}" for i in range(25)]
        payload = middleware._build_human_input_payload(
            {
                "question": "Details please",
                "clarification_type": "missing_info",
                "fields": [{"name": "category", "type": "select", "options": options}],
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["input_mode"] == "free_text"
        assert "fields" not in payload

    def test_overlong_field_text_degrades_whole_form(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Details please",
                "clarification_type": "missing_info",
                "fields": [{"name": "amount", "label": "x" * 201, "type": "number"}],
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["input_mode"] == "free_text"
        assert "fields" not in payload

    def test_top_level_options_are_trimmed_and_blank_dropped(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Which env?",
                "clarification_type": "approach_choice",
                "options": [" dev ", "", "prod", "dev"],
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["options"] == [
            {"id": "option-1", "label": "dev", "value": "dev"},
            {"id": "option-2", "label": "prod", "value": "prod"},
        ]

    def test_unhashable_field_type_degrades_to_text_not_crash(self, middleware):
        """`type: []` / `type: {}` are legal JSON from a model; an unhashable
        membership check would raise TypeError and (with return_direct=True)
        end the turn with an error instead of any card or fallback."""
        for bad_type in [[], {}, ["select"], {"t": "select"}]:
            payload = middleware._build_human_input_payload(
                {
                    "question": "Details please",
                    "clarification_type": "missing_info",
                    "fields": [{"name": "amount", "type": bad_type}],
                },
                tool_call_id="call-abc",
                request_id="clarification:call-abc",
            )

            assert payload["fields"][0]["type"] == "text"

    def test_unhashable_clarification_type_does_not_crash(self, middleware):
        """Same crash class as unhashable field types: `clarification_type: []`
        must not raise in the icon lookup or payload builder."""
        from langgraph.types import Command

        request = SimpleNamespace(
            tool_call={
                "name": "ask_clarification",
                "id": "call-clarify-1",
                "args": {"question": "q?", "clarification_type": [], "fields": [{"name": "amount", "type": []}]},
            },
            runtime=None,
        )

        result = middleware.wrap_tool_call(request, lambda _req: pytest.fail("handler should not be called"))

        assert isinstance(result, Command)
        message = result.update["messages"][0]
        assert message.artifact["human_input"]["input_mode"] == "form"

    def test_serialized_fields_over_byte_budget_degrade_whole_form(self, middleware):
        """Per-item caps alone allow a form whose IM text fallback exceeds
        channel limits (Slack 40k chars, Feishu ~30KB card); a total serialized
        byte budget must bound the whole definition."""
        fields = [
            {
                "name": f"field_{i}",
                "label": "标" * 190,
                "type": "select",
                "options": ["选" * 190 + str(j) for j in range(20)],
            }
            for i in range(16)
        ]
        payload = middleware._build_human_input_payload(
            {"question": "Details please", "clarification_type": "missing_info", "fields": fields},
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["input_mode"] == "free_text"
        assert "fields" not in payload

    def test_accepted_forms_keep_text_fallback_under_channel_limits(self, middleware):
        """Boundary: any form the byte budget accepts must produce an IM text
        fallback deliverable to the strictest supported channel (~30KB)."""
        # Grow a form until the budget rejects it; the largest accepted form's
        # fallback must stay under the channel bound.
        largest_accepted_fallback = None
        for count in range(1, 17):
            fields = [
                {
                    "name": f"field_{i}",
                    "label": "标" * 150,
                    "type": "select",
                    "options": ["选" * 100 + str(j) for j in range(10)],
                }
                for i in range(count)
            ]
            args = {"question": "Q", "clarification_type": "missing_info", "fields": fields}
            payload = middleware._build_human_input_payload(args, tool_call_id="c", request_id="clarification:c")
            if payload["input_mode"] != "form":
                break
            largest_accepted_fallback = middleware._format_clarification_message(args)

        assert largest_accepted_fallback is not None
        assert len(largest_accepted_fallback.encode("utf-8")) < 30_000

    def test_required_accepts_integer_serialization(self, middleware):
        """Some providers emit 1/0 for booleans; `required: 1` must not
        silently flip a model-intended required field to optional."""
        payload = middleware._build_human_input_payload(
            {
                "question": "Details please",
                "clarification_type": "missing_info",
                "fields": [
                    {"name": "amount", "type": "number", "required": 1},
                    {"name": "note", "type": "text", "required": 0},
                ],
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["fields"][0]["required"] is True
        assert payload["fields"][1]["required"] is False

    def test_field_placeholder_is_preserved(self, middleware):
        payload = middleware._build_human_input_payload(
            {
                "question": "Details please",
                "clarification_type": "missing_info",
                "fields": [{"name": "note", "placeholder": "Optional remarks"}],
            },
            tool_call_id="call-abc",
            request_id="clarification:call-abc",
        )

        assert payload["fields"][0]["placeholder"] == "Optional remarks"

    def test_form_fallback_text_lists_fields(self, middleware):
        result = middleware._format_clarification_message(
            {
                "question": "Please provide the expense details.",
                "clarification_type": "missing_info",
                "fields": self._fields(),
            }
        )

        assert "1. Amount (required)" in result
        assert "2. Category (required) — options: travel / meals" in result
        assert "3. Receipts — options: A-1 / A-2 (multiple allowed)" in result
        assert "4. note" in result
        assert "Please reply with a value for each field." in result


class TestClarificationToolSchema:
    """The tool schema must expose the v2 form parameter (request-side only)."""

    def test_tool_exposes_fields_argument(self):
        from deerflow.tools.builtins.clarification_tool import ask_clarification_tool

        schema = ask_clarification_tool.args
        assert "fields" in schema
        # The reply protocol stays v1 (text/option): no top-level multi_select
        # mode — a standalone multi-select question is a one-field form.
        assert "multi_select" not in schema

    def test_fields_item_schema_is_typed(self):
        """The provider-facing schema must expose the field item shape (typed
        via ClarificationFormField), not an opaque object relying on the
        docstring alone."""
        from langchain_core.utils.function_calling import convert_to_openai_tool

        from deerflow.tools.builtins.clarification_tool import ask_clarification_tool

        parameters = convert_to_openai_tool(ask_clarification_tool)["function"]["parameters"]
        items = parameters["properties"]["fields"]["anyOf"][0]["items"]

        assert items["required"] == ["name"]
        assert sorted(items["properties"].keys()) == ["label", "name", "options", "placeholder", "required", "type"]
        assert items["properties"]["type"]["enum"] == ["text", "textarea", "number", "select", "multi_select", "checkbox", "date"]


class TestClarificationCommandIdempotency:
    """Clarification tool-call retries should not duplicate messages in state."""

    def test_repeated_tool_call_uses_stable_message_id(self, middleware):
        request = SimpleNamespace(
            tool_call={
                "name": "ask_clarification",
                "id": "call-clarify-1",
                "args": {
                    "question": "Which environment should I use?",
                    "clarification_type": "approach_choice",
                    "options": ["dev", "prod"],
                },
            }
        )

        first = middleware.wrap_tool_call(request, lambda _req: pytest.fail("handler should not be called"))
        second = middleware.wrap_tool_call(request, lambda _req: pytest.fail("handler should not be called"))

        first_message = first.update["messages"][0]
        second_message = second.update["messages"][0]

        assert first_message.id == "clarification:call-clarify-1"
        assert second_message.id == first_message.id
        assert second_message.tool_call_id == first_message.tool_call_id
        assert first_message.artifact["human_input"]["request_id"] == "clarification:call-clarify-1"
        assert first_message.artifact["human_input"]["tool_call_id"] == "call-clarify-1"
        assert first_message.artifact["human_input"]["clarification_type"] == "approach_choice"
        assert first_message.artifact["human_input"]["input_mode"] == "choice_with_other"

        merged = add_messages(add_messages([], [first_message]), [second_message])

        assert len(merged) == 1
        assert merged[0].id == "clarification:call-clarify-1"
        assert merged[0].content == first_message.content
        assert merged[0].artifact == first_message.artifact

    def test_tool_message_model_dump_preserves_human_input_artifact(self, middleware):
        request = SimpleNamespace(
            tool_call={
                "name": "ask_clarification",
                "id": "call-clarify-1",
                "args": {
                    "question": "Which environment should I use?",
                    "clarification_type": "approach_choice",
                    "options": ["dev", "prod"],
                },
            }
        )

        result = middleware.wrap_tool_call(request, lambda _req: pytest.fail("handler should not be called"))
        message = result.update["messages"][0]
        dumped = message.model_dump()

        assert dumped["artifact"]["human_input"]["request_id"] == "clarification:call-clarify-1"
        assert dumped["artifact"]["human_input"]["options"] == [
            {"id": "option-1", "label": "dev", "value": "dev"},
            {"id": "option-2", "label": "prod", "value": "prod"},
        ]
        assert "Which environment should I use?" in dumped["content"]


class TestClarificationDisabled:
    """When ``disable_clarification`` is set in runtime context, a clarification
    must NOT interrupt the run — it returns a ToolMessage nudging the agent to
    proceed, so non-interactive channels (GitHub) don't dead-end."""

    def _request(self, *, runtime_context):
        return SimpleNamespace(
            tool_call={
                "name": "ask_clarification",
                "id": "call-clarify-1",
                "args": {"question": "Should I create the issue?", "clarification_type": "suggestion"},
            },
            runtime=SimpleNamespace(context=runtime_context),
        )

    def test_disabled_returns_toolmessage_not_command(self, middleware):
        request = self._request(runtime_context={"disable_clarification": True})
        result = middleware.wrap_tool_call(request, lambda _req: pytest.fail("handler should not be called"))
        # Not a Command(goto=END) — a plain ToolMessage so the loop continues.
        from langchain_core.messages import ToolMessage

        assert isinstance(result, ToolMessage)
        assert result.tool_call_id == "call-clarify-1"
        assert result.artifact is None

    def test_disabled_message_tells_agent_to_proceed(self, middleware):
        request = self._request(runtime_context={"disable_clarification": True})
        result = middleware.wrap_tool_call(request, lambda _req: pytest.fail("handler should not be called"))
        assert "disabled" in result.content.lower()
        assert "proceed" in result.content.lower()

    def test_disabled_async_path(self, middleware):
        request = self._request(runtime_context={"disable_clarification": True})

        async def handler(_req):
            return pytest.fail("handler should not be called")

        import asyncio

        result = asyncio.run(middleware.awrap_tool_call(request, handler))
        from langchain_core.messages import ToolMessage

        assert isinstance(result, ToolMessage)

    def test_not_disabled_still_interrupts(self, middleware):
        """Without the flag, the original goto=END behavior is preserved."""
        from langgraph.types import Command

        request = self._request(runtime_context={})  # no disable_clarification
        result = middleware.wrap_tool_call(request, lambda _req: pytest.fail("handler should not be called"))
        assert isinstance(result, Command)
        assert result.goto == "__end__"

    def test_no_runtime_context_still_interrupts(self, middleware):
        """Defensive: missing runtime/context falls back to interrupting."""
        from langgraph.types import Command

        request = SimpleNamespace(
            tool_call={
                "name": "ask_clarification",
                "id": "c1",
                "args": {"question": "q?", "clarification_type": "missing_info"},
            },
            runtime=None,
        )
        result = middleware.wrap_tool_call(request, lambda _req: pytest.fail("handler should not be called"))
        assert isinstance(result, Command)

    def test_non_clarification_tool_call_unaffected_by_flag(self, middleware):
        """The flag only affects ask_clarification; other tools run normally."""
        other = SimpleNamespace(
            tool_call={"name": "bash", "id": "b1", "args": {"command": "echo hi"}},
            runtime=SimpleNamespace(context={"disable_clarification": True}),
        )
        sentinel = "ran"
        result = middleware.wrap_tool_call(other, lambda _req: sentinel)
        assert result == sentinel

    def test_missing_tool_call_id_still_gets_stable_message_id(self, middleware):
        request = SimpleNamespace(
            tool_call={
                "name": "ask_clarification",
                "args": {
                    "question": "Which environment should I use?",
                    "clarification_type": "missing_info",
                },
            }
        )

        first = middleware.wrap_tool_call(request, lambda _req: pytest.fail("handler should not be called"))
        second = middleware.wrap_tool_call(request, lambda _req: pytest.fail("handler should not be called"))

        first_message = first.update["messages"][0]
        second_message = second.update["messages"][0]

        assert first_message.id.startswith("clarification:")
        assert second_message.id == first_message.id

        merged = add_messages(add_messages([], [first_message]), [second_message])

        assert len(merged) == 1