agent-framework/python/packages/azure-ai/tests/test_azure_ai_client.py

# Copyright (c) Microsoft. All rights reserved.

import json
import os
import sys
import warnings
from collections.abc import AsyncGenerator, AsyncIterator
from contextlib import asynccontextmanager
from typing import Annotated, Any
from unittest.mock import AsyncMock, MagicMock, patch
from uuid import uuid4

import pytest
from agent_framework import (
    Annotation,
    ChatOptions,
    ChatResponse,
    ChatResponseUpdate,
    Content,
    Message,
    ResponseStream,
    SupportsChatGetResponse,
    tool,
)
from agent_framework._settings import load_settings
from agent_framework_openai._chat_client import RawOpenAIChatClient
from azure.ai.projects.aio import AIProjectClient
from azure.ai.projects.models import (
    ApproximateLocation,
    AutoCodeInterpreterToolParam,
    CodeInterpreterTool,
    FileSearchTool,
    ImageGenTool,
    MCPTool,
    TextResponseFormatJsonSchema,
    WebSearchPreviewTool,
)
from azure.core.exceptions import ResourceNotFoundError
from azure.identity.aio import AzureCliCredential
from openai.types.responses.parsed_response import ParsedResponse
from openai.types.responses.response import Response as OpenAIResponse
from pydantic import BaseModel, ConfigDict, Field
from pytest import fixture

from agent_framework_azure_ai import AzureAIClient, AzureAISettings  # noqa: E402
from agent_framework_azure_ai._shared import from_azure_ai_tools  # noqa: E402

warnings.filterwarnings(
    "ignore",
    message=r"RawAzureAIClient is deprecated\..*",
    category=DeprecationWarning,
)
warnings.filterwarnings(
    "ignore",
    message=r"AzureAIClient is deprecated\..*",
    category=DeprecationWarning,
)

pytestmark = pytest.mark.filterwarnings("ignore:AzureAIClient is deprecated\\..*:DeprecationWarning")


@pytest.fixture
def mock_project_client() -> MagicMock:
    """Fixture that provides a mock AIProjectClient."""
    mock_client = MagicMock()

    # Mock agents property
    mock_client.agents = MagicMock()
    mock_client.agents.create_version = AsyncMock()

    # Mock conversations property
    mock_client.conversations = MagicMock()
    mock_client.conversations.create = AsyncMock()

    # Mock telemetry property
    mock_client.telemetry = MagicMock()
    mock_client.telemetry.get_application_insights_connection_string = AsyncMock()

    # Mock get_openai_client method
    mock_client.get_openai_client = AsyncMock()

    # Mock close method
    mock_client.close = AsyncMock()

    return mock_client


@asynccontextmanager
async def temporary_chat_client(agent_name: str) -> AsyncIterator[AzureAIClient]:
    """Async context manager that creates an Azure AI agent and yields an `AzureAIClient`.

    The underlying agent version is cleaned up automatically after use.
    Tests can construct their own `Agent` instances from the yielded client.
    """
    endpoint = os.environ["AZURE_AI_PROJECT_ENDPOINT"]
    async with (
        AzureCliCredential() as credential,
        AIProjectClient(endpoint=endpoint, credential=credential) as project_client,
    ):
        client = AzureAIClient(
            project_client=project_client,
            agent_name=agent_name,
        )
        try:
            yield client
        finally:
            await project_client.agents.delete(agent_name=agent_name)


def create_test_azure_ai_client(
    mock_project_client: MagicMock,
    agent_name: str | None = None,
    agent_version: str | None = None,
    conversation_id: str | None = None,
    azure_ai_settings: AzureAISettings | None = None,
    should_close_client: bool = False,
    use_latest_version: bool | None = None,
) -> AzureAIClient:
    """Helper function to create AzureAIClient instances for testing, bypassing normal validation."""
    if azure_ai_settings is None:
        azure_ai_settings = load_settings(AzureAISettings, env_prefix="AZURE_AI_")

    # Create client instance directly
    client = object.__new__(AzureAIClient)

    # Set attributes directly
    client.project_client = mock_project_client
    client.credential = None
    client.agent_name = agent_name
    client.agent_version = agent_version
    client.agent_description = None
    client.use_latest_version = use_latest_version
    client.model_id = azure_ai_settings.get("model_deployment_name")
    client.conversation_id = conversation_id
    client._is_application_endpoint = False  # type: ignore
    client._should_close_client = should_close_client  # type: ignore
    client.warn_runtime_tools_and_structure_changed = False  # type: ignore
    client._created_agent_tool_names = set()  # type: ignore
    client._created_agent_structured_output_signature = None  # type: ignore
    client.additional_properties = {}
    client.chat_middleware = []

    # Mock the OpenAI client attribute
    mock_openai_client = MagicMock()
    mock_openai_client.conversations = MagicMock()
    mock_openai_client.conversations.create = AsyncMock()
    client.client = mock_openai_client

    return client


def test_azure_ai_settings_init(azure_ai_unit_test_env: dict[str, str]) -> None:
    """Test AzureAISettings initialization."""
    settings = load_settings(AzureAISettings, env_prefix="AZURE_AI_")

    assert settings["project_endpoint"] == azure_ai_unit_test_env["AZURE_AI_PROJECT_ENDPOINT"]
    assert settings["model_deployment_name"] == azure_ai_unit_test_env["AZURE_AI_MODEL_DEPLOYMENT_NAME"]


def test_azure_ai_settings_init_with_explicit_values() -> None:
    """Test AzureAISettings initialization with explicit values."""
    settings = load_settings(
        AzureAISettings,
        env_prefix="AZURE_AI_",
        project_endpoint="https://custom-endpoint.com/",
        model_deployment_name="custom-model",
    )

    assert settings["project_endpoint"] == "https://custom-endpoint.com/"
    assert settings["model_deployment_name"] == "custom-model"


def test_init_with_project_client(mock_project_client: MagicMock) -> None:
    """Test AzureAIClient initialization with existing project_client."""
    with patch("agent_framework_azure_ai._client.load_settings") as mock_load_settings:
        mock_load_settings.return_value = {"project_endpoint": None, "model_deployment_name": "test-model"}

        client = AzureAIClient(
            project_client=mock_project_client,
            agent_name="test-agent",
            agent_version="1.0",
        )

        assert client.project_client is mock_project_client
        assert client.agent_name == "test-agent"
        assert client.agent_version == "1.0"
        assert not client._should_close_client  # type: ignore
        assert isinstance(client, SupportsChatGetResponse)


def test_init_auto_create_client(
    azure_ai_unit_test_env: dict[str, str],
    mock_azure_credential: MagicMock,
) -> None:
    """Test AzureAIClient initialization with auto-created project_client."""
    with patch("agent_framework_azure_ai._client.AIProjectClient") as mock_ai_project_client:
        mock_project_client = MagicMock()
        mock_ai_project_client.return_value = mock_project_client

        client = AzureAIClient(
            project_endpoint=azure_ai_unit_test_env["AZURE_AI_PROJECT_ENDPOINT"],
            model_deployment_name=azure_ai_unit_test_env["AZURE_AI_MODEL_DEPLOYMENT_NAME"],
            credential=mock_azure_credential,
            agent_name="test-agent",
        )

        assert client.project_client is mock_project_client
        assert client.agent_name == "test-agent"
        assert client._should_close_client  # type: ignore

        # Verify AIProjectClient was called with correct parameters
        mock_ai_project_client.assert_called_once()


def test_init_missing_project_endpoint() -> None:
    """Test AzureAIClient initialization when project_endpoint is missing and no project_client provided."""
    with patch("agent_framework_azure_ai._client.load_settings") as mock_load_settings:
        mock_load_settings.return_value = {"project_endpoint": None, "model_deployment_name": "test-model"}

        with pytest.raises(ValueError, match="Azure AI project endpoint is required"):
            AzureAIClient(credential=MagicMock())


def test_init_missing_credential(azure_ai_unit_test_env: dict[str, str]) -> None:
    """Test AzureAIClient.__init__ when credential is missing and no project_client provided."""
    with pytest.raises(ValueError, match="Azure credential is required when project_client is not provided"):
        AzureAIClient(
            project_endpoint=azure_ai_unit_test_env["AZURE_AI_PROJECT_ENDPOINT"],
            model_deployment_name=azure_ai_unit_test_env["AZURE_AI_MODEL_DEPLOYMENT_NAME"],
        )


async def test_get_agent_reference_or_create_existing_version(
    mock_project_client: MagicMock,
) -> None:
    """Test _get_agent_reference_or_create when agent_version is already provided."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="existing-agent", agent_version="1.0")

    agent_ref = await client._get_agent_reference_or_create({}, None)  # type: ignore

    assert agent_ref == {"name": "existing-agent", "version": "1.0", "type": "agent_reference"}


async def test_get_agent_reference_or_create_missing_agent_name(
    mock_project_client: MagicMock,
) -> None:
    """Test _get_agent_reference_or_create raises when agent_name is missing."""
    client = create_test_azure_ai_client(mock_project_client, agent_name=None)

    with pytest.raises(ValueError, match="Agent name is required"):
        await client._get_agent_reference_or_create({}, None)  # type: ignore


async def test_get_agent_reference_or_create_new_agent(
    mock_project_client: MagicMock,
    azure_ai_unit_test_env: dict[str, str],
) -> None:
    """Test _get_agent_reference_or_create when creating a new agent."""
    azure_ai_settings = load_settings(
        AzureAISettings,
        env_prefix="AZURE_AI_",
        model_deployment_name=azure_ai_unit_test_env["AZURE_AI_MODEL_DEPLOYMENT_NAME"],
    )
    client = create_test_azure_ai_client(
        mock_project_client, agent_name="new-agent", azure_ai_settings=azure_ai_settings
    )

    # Mock agent creation response
    mock_agent = MagicMock()
    mock_agent.name = "new-agent"
    mock_agent.version = "1.0"
    mock_project_client.agents.create_version = AsyncMock(return_value=mock_agent)

    run_options = {"model": azure_ai_settings.get("model_deployment_name")}
    agent_ref = await client._get_agent_reference_or_create(run_options, None)  # type: ignore

    assert agent_ref == {"name": "new-agent", "version": "1.0", "type": "agent_reference"}
    assert client.agent_name == "new-agent"
    assert client.agent_version == "1.0"


async def test_get_agent_reference_missing_model(
    mock_project_client: MagicMock,
) -> None:
    """Test _get_agent_reference_or_create when model is missing for agent creation."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent")

    with pytest.raises(ValueError, match="Model deployment name is required for agent creation"):
        await client._get_agent_reference_or_create({}, None)  # type: ignore


async def test_prepare_messages_for_azure_ai_with_system_messages(
    mock_project_client: MagicMock,
) -> None:
    """Test _prepare_messages_for_azure_ai converts system/developer messages to instructions."""
    client = create_test_azure_ai_client(mock_project_client)

    messages = [
        Message(role="system", contents=[Content.from_text(text="You are a helpful assistant.")]),
        Message(role="user", contents=[Content.from_text(text="Hello")]),
        Message(role="assistant", contents=[Content.from_text(text="System response")]),
    ]

    result_messages, instructions = client._prepare_messages_for_azure_ai(messages)  # type: ignore

    assert len(result_messages) == 2
    assert result_messages[0].role == "user"
    assert result_messages[1].role == "assistant"
    assert instructions == "You are a helpful assistant."


async def test_prepare_messages_for_azure_ai_no_system_messages(
    mock_project_client: MagicMock,
) -> None:
    """Test _prepare_messages_for_azure_ai with no system/developer messages."""
    client = create_test_azure_ai_client(mock_project_client)

    messages = [
        Message(role="user", contents=[Content.from_text(text="Hello")]),
        Message(role="assistant", contents=[Content.from_text(text="Hi there!")]),
    ]

    result_messages, instructions = client._prepare_messages_for_azure_ai(messages)  # type: ignore

    assert len(result_messages) == 2
    assert instructions is None


def test_transform_input_for_azure_ai(mock_project_client: MagicMock) -> None:
    """Test _transform_input_for_azure_ai adds required fields for Azure AI schema.

    WORKAROUND TEST: Azure AI Projects API requires 'type' at item level and
    'annotations' in output_text content items, which OpenAI's Responses API does not require.
    See: https://github.com/Azure/azure-sdk-for-python/issues/44493
    See: https://github.com/microsoft/agent-framework/issues/2926
    """
    client = create_test_azure_ai_client(mock_project_client)

    # Input in OpenAI Responses API format (what agent-framework generates)
    openai_format_input = [
        {
            "role": "user",
            "content": [
                {"type": "input_text", "text": "Hello"},
            ],
        },
        {
            "role": "assistant",
            "content": [
                {"type": "output_text", "text": "Hi there!"},
            ],
        },
    ]

    result = client._transform_input_for_azure_ai(openai_format_input)  # type: ignore

    # Verify 'type': 'message' added at item level
    assert result[0]["type"] == "message"
    assert result[1]["type"] == "message"

    # Verify 'annotations' added ONLY to output_text (assistant) content, NOT input_text (user)
    assert result[0]["content"][0]["type"] == "input_text"  # user content type preserved
    assert "annotations" not in result[0]["content"][0]  # user message - no annotations
    assert result[1]["content"][0]["type"] == "output_text"  # assistant content type preserved
    assert result[1]["content"][0]["annotations"] == []  # assistant message - has annotations

    # Verify original fields preserved
    assert result[0]["role"] == "user"
    assert result[0]["content"][0]["text"] == "Hello"
    assert result[1]["role"] == "assistant"
    assert result[1]["content"][0]["text"] == "Hi there!"


def test_transform_input_preserves_existing_fields(mock_project_client: MagicMock) -> None:
    """Test _transform_input_for_azure_ai preserves existing type and annotations."""
    client = create_test_azure_ai_client(mock_project_client)

    # Input that already has the fields (shouldn't duplicate)
    input_with_fields = [
        {
            "type": "message",
            "role": "assistant",
            "content": [
                {"type": "output_text", "text": "Hello", "annotations": [{"some": "annotation"}]},
            ],
        },
    ]

    result = client._transform_input_for_azure_ai(input_with_fields)  # type: ignore

    # Should preserve existing values, not overwrite
    assert result[0]["type"] == "message"
    assert result[0]["content"][0]["annotations"] == [{"some": "annotation"}]


def test_transform_input_handles_non_dict_content(mock_project_client: MagicMock) -> None:
    """Test _transform_input_for_azure_ai handles non-dict content items."""
    client = create_test_azure_ai_client(mock_project_client)

    # Input with string content (edge case)
    input_with_string_content = [
        {
            "role": "user",
            "content": ["plain string content"],
        },
    ]

    result = client._transform_input_for_azure_ai(input_with_string_content)  # type: ignore

    # Should add 'type': 'message' at item level even with non-dict content
    assert result[0]["type"] == "message"
    # Non-dict content items should be preserved without modification
    assert result[0]["content"] == ["plain string content"]


async def test_prepare_options_basic(mock_project_client: MagicMock) -> None:
    """Test prepare_options basic functionality."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent", agent_version="1.0")

    messages = [Message(role="user", contents=[Content.from_text(text="Hello")])]

    with (
        patch(
            "agent_framework_openai._chat_client.RawOpenAIChatClient._prepare_options",
            return_value={"model": "test-model"},
        ),
        patch.object(
            client,
            "_get_agent_reference_or_create",
            return_value={"name": "test-agent", "version": "1.0", "type": "agent_reference"},
        ),
    ):
        run_options = await client._prepare_options(messages, {})

        assert "extra_body" in run_options
        assert run_options["extra_body"]["agent_reference"]["name"] == "test-agent"


@pytest.mark.parametrize(
    "endpoint,expects_agent",
    [
        ("https://example.com/api/projects/my-project/applications/my-application/protocols", False),
        ("https://example.com/api/projects/my-project", True),
    ],
)
async def test_prepare_options_with_application_endpoint(
    mock_azure_credential: MagicMock, endpoint: str, expects_agent: bool
) -> None:
    client = AzureAIClient(
        project_endpoint=endpoint,
        model_deployment_name="test-model",
        credential=mock_azure_credential,
        agent_name="test-agent",
        agent_version="1",
    )

    messages = [Message(role="user", contents=[Content.from_text(text="Hello")])]

    with (
        patch(
            "agent_framework_openai._chat_client.RawOpenAIChatClient._prepare_options",
            return_value={"model": "test-model"},
        ),
        patch.object(
            client,
            "_get_agent_reference_or_create",
            return_value={"name": "test-agent", "version": "1", "type": "agent_reference"},
        ),
    ):
        run_options = await client._prepare_options(messages, {})

    if expects_agent:
        assert "extra_body" in run_options
        assert run_options["extra_body"]["agent_reference"]["name"] == "test-agent"
    else:
        assert "extra_body" not in run_options


@pytest.mark.parametrize(
    "endpoint,expects_agent",
    [
        ("https://example.com/api/projects/my-project/applications/my-application/protocols", False),
        ("https://example.com/api/projects/my-project", True),
    ],
)
async def test_prepare_options_with_application_project_client(
    mock_project_client: MagicMock, endpoint: str, expects_agent: bool
) -> None:
    mock_project_client._config = MagicMock()
    mock_project_client._config.endpoint = endpoint

    client = AzureAIClient(
        project_client=mock_project_client,
        model_deployment_name="test-model",
        agent_name="test-agent",
        agent_version="1",
    )

    messages = [Message(role="user", contents=[Content.from_text(text="Hello")])]

    with (
        patch(
            "agent_framework_openai._chat_client.RawOpenAIChatClient._prepare_options",
            return_value={"model": "test-model"},
        ),
        patch.object(
            client,
            "_get_agent_reference_or_create",
            return_value={"name": "test-agent", "version": "1", "type": "agent_reference"},
        ),
    ):
        run_options = await client._prepare_options(messages, {})

    if expects_agent:
        assert "extra_body" in run_options
        assert run_options["extra_body"]["agent_reference"]["name"] == "test-agent"
    else:
        assert "extra_body" not in run_options


def test_update_agent_name_and_description(mock_project_client: MagicMock) -> None:
    """Test _update_agent_name_and_description method."""
    client = create_test_azure_ai_client(mock_project_client)

    # Test updating agent name when current is None
    with patch.object(client, "_update_agent_name_and_description") as mock_update:
        mock_update.return_value = None
        client._update_agent_name_and_description("new-agent")  # type: ignore
        mock_update.assert_called_once_with("new-agent")

    # Test behavior when agent name is updated
    assert client.agent_name is None  # Should remain None since we didn't actually update
    client.agent_name = "test-agent"  # Manually set for the test

    # Test with None input
    with patch.object(client, "_update_agent_name_and_description") as mock_update:
        mock_update.return_value = None
        client._update_agent_name_and_description(None)  # type: ignore
        mock_update.assert_called_once_with(None)


def test_as_agent_uses_client_agent_name_as_default(mock_project_client: MagicMock) -> None:
    """Test that as_agent() defaults Agent.name to client.agent_name when name is not provided."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="my_agent")
    client.agent_description = "my description"

    agent = client.as_agent(instructions="You are helpful.")

    assert agent.name == "my_agent"
    assert agent.description == "my description"


def test_as_agent_explicit_name_overrides_client_agent_name(mock_project_client: MagicMock) -> None:
    """Test that an explicit name passed to as_agent() takes precedence over client.agent_name."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="client_name")
    client.agent_description = "client description"

    agent = client.as_agent(name="explicit_name", description="explicit description", instructions="You are helpful.")

    assert agent.name == "explicit_name"
    assert agent.description == "explicit description"


def test_as_agent_no_name_anywhere(mock_project_client: MagicMock) -> None:
    """Test that Agent.name is None when neither as_agent name nor client.agent_name is provided."""
    client = create_test_azure_ai_client(mock_project_client)

    agent = client.as_agent(instructions="You are helpful.")

    assert agent.name is None


def test_as_agent_empty_string_preserves_explicit_value(mock_project_client: MagicMock) -> None:
    """Test that empty-string name/description are preserved and do not fall back to client defaults."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="client_name")
    client.agent_description = "client description"

    agent = client.as_agent(name="", description="", instructions="You are helpful.")

    assert agent.name == ""
    assert agent.description == ""


async def test_async_context_manager(mock_project_client: MagicMock) -> None:
    """Test async context manager functionality."""
    client = create_test_azure_ai_client(mock_project_client, should_close_client=True)

    mock_project_client.close = AsyncMock()

    async with client as ctx_client:
        assert ctx_client is client

    # Should call close after exiting context
    mock_project_client.close.assert_called_once()


async def test_close_method(mock_project_client: MagicMock) -> None:
    """Test close method."""
    client = create_test_azure_ai_client(mock_project_client, should_close_client=True)

    mock_project_client.close = AsyncMock()

    await client.close()

    mock_project_client.close.assert_called_once()


async def test_close_client_when_should_close_false(mock_project_client: MagicMock) -> None:
    """Test _close_client_if_needed when should_close_client is False."""
    client = create_test_azure_ai_client(mock_project_client, should_close_client=False)

    mock_project_client.close = AsyncMock()

    await client._close_client_if_needed()  # type: ignore

    # Should not call close when should_close_client is False
    mock_project_client.close.assert_not_called()


async def test_configure_azure_monitor_success(mock_project_client: MagicMock) -> None:
    """Test configure_azure_monitor successfully configures Azure Monitor."""
    client = create_test_azure_ai_client(mock_project_client)

    # Mock the telemetry connection string retrieval
    mock_project_client.telemetry.get_application_insights_connection_string = AsyncMock(
        return_value="InstrumentationKey=test-key;IngestionEndpoint=https://test.endpoint"
    )

    mock_configure = MagicMock()
    mock_views = MagicMock(return_value=[])
    mock_resource = MagicMock()
    mock_enable = MagicMock()

    with (
        patch.dict(
            "sys.modules",
            {"azure.monitor.opentelemetry": MagicMock(configure_azure_monitor=mock_configure)},
        ),
        patch("agent_framework.observability.create_metric_views", mock_views),
        patch("agent_framework.observability.create_resource", return_value=mock_resource),
        patch("agent_framework.observability.enable_instrumentation", mock_enable),
    ):
        await client.configure_azure_monitor(enable_sensitive_data=True)

        # Verify connection string was retrieved
        mock_project_client.telemetry.get_application_insights_connection_string.assert_called_once()

        # Verify Azure Monitor was configured
        mock_configure.assert_called_once()
        call_kwargs = mock_configure.call_args[1]
        assert call_kwargs["connection_string"] == "InstrumentationKey=test-key;IngestionEndpoint=https://test.endpoint"

        # Verify instrumentation was enabled with sensitive data flag
        mock_enable.assert_called_once_with(enable_sensitive_data=True)


async def test_configure_azure_monitor_resource_not_found(mock_project_client: MagicMock) -> None:
    """Test configure_azure_monitor handles ResourceNotFoundError gracefully."""
    client = create_test_azure_ai_client(mock_project_client)

    # Mock the telemetry to raise ResourceNotFoundError
    mock_project_client.telemetry.get_application_insights_connection_string = AsyncMock(
        side_effect=ResourceNotFoundError("No Application Insights found")
    )

    # Should not raise, just log warning and return
    await client.configure_azure_monitor()

    # Verify connection string retrieval was attempted
    mock_project_client.telemetry.get_application_insights_connection_string.assert_called_once()


async def test_configure_azure_monitor_import_error(mock_project_client: MagicMock) -> None:
    """Test configure_azure_monitor raises ImportError when azure-monitor-opentelemetry is not installed."""
    client = create_test_azure_ai_client(mock_project_client)

    # Mock the telemetry connection string retrieval
    mock_project_client.telemetry.get_application_insights_connection_string = AsyncMock(
        return_value="InstrumentationKey=test-key"
    )

    # Mock the import to fail
    with (
        patch.dict(sys.modules, {"azure.monitor.opentelemetry": None}),
        patch("builtins.__import__", side_effect=ImportError("No module named 'azure.monitor.opentelemetry'")),
        pytest.raises(ImportError, match="azure-monitor-opentelemetry is required"),
    ):
        await client.configure_azure_monitor()


async def test_configure_azure_monitor_with_custom_resource(mock_project_client: MagicMock) -> None:
    """Test configure_azure_monitor uses custom resource when provided."""
    client = create_test_azure_ai_client(mock_project_client)

    mock_project_client.telemetry.get_application_insights_connection_string = AsyncMock(
        return_value="InstrumentationKey=test-key"
    )

    custom_resource = MagicMock()
    mock_configure = MagicMock()

    with (
        patch.dict(
            "sys.modules",
            {"azure.monitor.opentelemetry": MagicMock(configure_azure_monitor=mock_configure)},
        ),
        patch("agent_framework.observability.create_metric_views") as mock_views,
        patch("agent_framework.observability.create_resource") as mock_create_resource,
        patch("agent_framework.observability.enable_instrumentation"),
    ):
        mock_views.return_value = []

        await client.configure_azure_monitor(resource=custom_resource)

        # Verify custom resource was used, not create_resource
        mock_create_resource.assert_not_called()
        call_kwargs = mock_configure.call_args[1]
        assert call_kwargs["resource"] is custom_resource


async def test_agent_creation_with_instructions(
    mock_project_client: MagicMock,
) -> None:
    """Test agent creation with combined instructions."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent")

    # Mock agent creation response
    mock_agent = MagicMock()
    mock_agent.name = "test-agent"
    mock_agent.version = "1.0"
    mock_project_client.agents.create_version = AsyncMock(return_value=mock_agent)

    run_options = {"model": "test-model"}
    chat_options = {"instructions": "Option instructions. "}
    messages_instructions = "Message instructions. "

    await client._get_agent_reference_or_create(run_options, messages_instructions, chat_options)  # type: ignore

    # Verify agent was created with combined instructions
    call_args = mock_project_client.agents.create_version.call_args
    assert call_args[1]["definition"].instructions == "Message instructions. Option instructions. "


async def test_agent_creation_with_instructions_from_chat_options(
    mock_project_client: MagicMock,
) -> None:
    """Test agent creation with instructions passed only via chat_options."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent")

    mock_agent = MagicMock()
    mock_agent.name = "test-agent"
    mock_agent.version = "1.0"
    mock_project_client.agents.create_version = AsyncMock(return_value=mock_agent)

    run_options = {"model": "test-model"}
    chat_options = {"instructions": "Chat options instructions."}

    await client._get_agent_reference_or_create(run_options, None, chat_options)  # type: ignore

    call_args = mock_project_client.agents.create_version.call_args
    assert call_args[1]["definition"].instructions == "Chat options instructions."


async def test_agent_creation_with_additional_args(
    mock_project_client: MagicMock,
) -> None:
    """Test agent creation with additional arguments."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent")

    # Mock agent creation response
    mock_agent = MagicMock()
    mock_agent.name = "test-agent"
    mock_agent.version = "1.0"
    mock_project_client.agents.create_version = AsyncMock(return_value=mock_agent)

    run_options = {"model": "test-model", "temperature": 0.9, "top_p": 0.8}
    messages_instructions = "Message instructions. "

    await client._get_agent_reference_or_create(run_options, messages_instructions)  # type: ignore

    # Verify agent was created with provided arguments
    call_args = mock_project_client.agents.create_version.call_args
    definition = call_args[1]["definition"]
    assert definition.temperature == 0.9
    assert definition.top_p == 0.8


async def test_agent_creation_with_tools(
    mock_project_client: MagicMock,
) -> None:
    """Test agent creation with tools."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent")

    # Mock agent creation response
    mock_agent = MagicMock()
    mock_agent.name = "test-agent"
    mock_agent.version = "1.0"
    mock_project_client.agents.create_version = AsyncMock(return_value=mock_agent)

    test_tools = [{"type": "function", "function": {"name": "test_tool"}}]
    run_options = {"model": "test-model", "tools": test_tools}

    await client._get_agent_reference_or_create(run_options, None)  # type: ignore

    # Verify agent was created with tools
    call_args = mock_project_client.agents.create_version.call_args
    assert call_args[1]["definition"].tools == test_tools


async def test_runtime_tools_override_logs_warning(
    mock_project_client: MagicMock,
) -> None:
    """Test warning is logged when runtime tools differ from creation-time tools."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent")

    mock_agent = MagicMock()
    mock_agent.name = "test-agent"
    mock_agent.version = "1.0"
    mock_project_client.agents.create_version = AsyncMock(return_value=mock_agent)
    messages = [Message(role="user", contents=[Content.from_text(text="Hello")])]

    with patch(
        "agent_framework_openai._chat_client.RawOpenAIChatClient._prepare_options",
        return_value={"model": "test-model", "tools": [{"type": "function", "name": "tool_one"}]},
    ):
        await client._prepare_options(messages, {})

    with (
        patch(
            "agent_framework_openai._chat_client.RawOpenAIChatClient._prepare_options",
            return_value={"model": "test-model", "tools": [{"type": "function", "name": "tool_two"}]},
        ),
        patch("agent_framework_azure_ai._client.logger.warning") as mock_warning,
    ):
        await client._prepare_options(messages, {})
    mock_warning.assert_called_once()
    assert "Use AzureOpenAIResponsesClient instead." in mock_warning.call_args[0][0]


async def test_prepare_options_logs_warning_for_tools_with_existing_agent_version(
    mock_project_client: MagicMock,
) -> None:
    """Test warning is logged when tools are supplied against an existing agent version."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent", agent_version="1.0")
    messages = [Message(role="user", contents=[Content.from_text(text="Hello")])]

    with (
        patch(
            "agent_framework_openai._chat_client.RawOpenAIChatClient._prepare_options",
            return_value={"model": "test-model", "tools": [{"type": "function", "name": "tool_one"}]},
        ),
        patch("agent_framework_azure_ai._client.logger.warning") as mock_warning,
    ):
        run_options = await client._prepare_options(messages, {})

    mock_warning.assert_called_once()
    assert "Use AzureOpenAIResponsesClient instead." in mock_warning.call_args[0][0]
    assert "tools" not in run_options


async def test_prepare_options_logs_warning_for_tools_on_application_endpoint(
    mock_project_client: MagicMock,
) -> None:
    """Test warning is logged when runtime tools are removed for application endpoints."""
    client = create_test_azure_ai_client(mock_project_client)
    client._is_application_endpoint = True  # type: ignore
    messages = [Message(role="user", contents=[Content.from_text(text="Hello")])]

    with (
        patch(
            "agent_framework_openai._chat_client.RawOpenAIChatClient._prepare_options",
            return_value={"model": "test-model", "tools": [{"type": "function", "name": "tool_one"}]},
        ),
        patch.object(client, "_get_agent_reference_or_create", new_callable=AsyncMock) as mock_get_agent_reference,
        patch("agent_framework_azure_ai._client.logger.warning") as mock_warning,
    ):
        run_options = await client._prepare_options(messages, {})

    mock_get_agent_reference.assert_not_called()
    mock_warning.assert_called_once()
    assert "Use AzureOpenAIResponsesClient instead." in mock_warning.call_args[0][0]
    assert "tools" not in run_options
    assert "extra_body" not in run_options


async def test_use_latest_version_existing_agent(
    mock_project_client: MagicMock,
) -> None:
    """Test _get_agent_reference_or_create when use_latest_version=True and agent exists."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="existing-agent", use_latest_version=True)

    # Mock existing agent response
    mock_existing_agent = MagicMock()
    mock_existing_agent.name = "existing-agent"
    mock_existing_agent.versions.latest.version = "2.5"
    mock_project_client.agents.get = AsyncMock(return_value=mock_existing_agent)

    run_options = {"model": "test-model"}
    agent_ref = await client._get_agent_reference_or_create(run_options, None)  # type: ignore

    # Verify existing agent was retrieved and used
    mock_project_client.agents.get.assert_called_once_with("existing-agent")
    mock_project_client.agents.create_version.assert_not_called()

    assert agent_ref == {"name": "existing-agent", "version": "2.5", "type": "agent_reference"}
    assert client.agent_name == "existing-agent"
    assert client.agent_version == "2.5"


async def test_use_latest_version_agent_not_found(
    mock_project_client: MagicMock,
) -> None:
    """Test _get_agent_reference_or_create when use_latest_version=True but agent doesn't exist."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="non-existing-agent", use_latest_version=True)

    # Mock ResourceNotFoundError when trying to retrieve agent
    mock_project_client.agents.get = AsyncMock(side_effect=ResourceNotFoundError("Agent not found"))

    # Mock agent creation response for fallback
    mock_created_agent = MagicMock()
    mock_created_agent.name = "non-existing-agent"
    mock_created_agent.version = "1.0"
    mock_project_client.agents.create_version = AsyncMock(return_value=mock_created_agent)

    run_options = {"model": "test-model"}
    agent_ref = await client._get_agent_reference_or_create(run_options, None)  # type: ignore

    # Verify retrieval was attempted and creation was used as fallback
    mock_project_client.agents.get.assert_called_once_with("non-existing-agent")
    mock_project_client.agents.create_version.assert_called_once()

    assert agent_ref == {"name": "non-existing-agent", "version": "1.0", "type": "agent_reference"}
    assert client.agent_name == "non-existing-agent"
    assert client.agent_version == "1.0"


async def test_use_latest_version_false(
    mock_project_client: MagicMock,
) -> None:
    """Test _get_agent_reference_or_create when use_latest_version=False (default behavior)."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent", use_latest_version=False)

    # Mock agent creation response
    mock_created_agent = MagicMock()
    mock_created_agent.name = "test-agent"
    mock_created_agent.version = "1.0"
    mock_project_client.agents.create_version = AsyncMock(return_value=mock_created_agent)

    run_options = {"model": "test-model"}
    agent_ref = await client._get_agent_reference_or_create(run_options, None)  # type: ignore

    # Verify retrieval was not attempted and creation was used directly
    mock_project_client.agents.get.assert_not_called()
    mock_project_client.agents.create_version.assert_called_once()

    assert agent_ref == {"name": "test-agent", "version": "1.0", "type": "agent_reference"}


async def test_use_latest_version_with_existing_agent_version(
    mock_project_client: MagicMock,
) -> None:
    """Test that use_latest_version is ignored when agent_version is already provided."""
    client = create_test_azure_ai_client(
        mock_project_client, agent_name="test-agent", agent_version="3.0", use_latest_version=True
    )

    agent_ref = await client._get_agent_reference_or_create({}, None)  # type: ignore

    # Verify neither retrieval nor creation was attempted since version is already set
    mock_project_client.agents.get.assert_not_called()
    mock_project_client.agents.create_version.assert_not_called()

    assert agent_ref == {"name": "test-agent", "version": "3.0", "type": "agent_reference"}


class ResponseFormatModel(BaseModel):
    """Test Pydantic model for response format testing."""

    name: str
    value: int
    description: str
    model_config = ConfigDict(extra="forbid")


class AlternateResponseFormatModel(BaseModel):
    """Alternate model for structured output warning checks."""

    summary: str
    confidence: float


async def test_agent_creation_with_response_format(
    mock_project_client: MagicMock,
) -> None:
    """Test agent creation with response_format configuration."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent")

    # Mock agent creation response
    mock_agent = MagicMock()
    mock_agent.name = "test-agent"
    mock_agent.version = "1.0"
    mock_project_client.agents.create_version = AsyncMock(return_value=mock_agent)

    run_options = {"model": "test-model"}
    chat_options = {"response_format": ResponseFormatModel}

    await client._get_agent_reference_or_create(run_options, None, chat_options)  # type: ignore

    # Verify agent was created with response format configuration
    call_args = mock_project_client.agents.create_version.call_args
    created_definition = call_args[1]["definition"]

    # Check that text format configuration was set
    assert hasattr(created_definition, "text")
    assert created_definition.text is not None

    # Check that the format is a TextResponseFormatJsonSchema
    assert hasattr(created_definition.text, "format")
    format_config = created_definition.text.format
    assert isinstance(format_config, TextResponseFormatJsonSchema)

    # Check the schema name matches the model class name
    assert format_config.name == "ResponseFormatModel"

    # Check that schema was generated correctly
    assert format_config.schema is not None
    schema = format_config.schema
    assert "properties" in schema
    assert "name" in schema["properties"]
    assert "value" in schema["properties"]
    assert "description" in schema["properties"]
    assert "additionalProperties" in schema


async def test_agent_creation_with_mapping_response_format(
    mock_project_client: MagicMock,
) -> None:
    """Test agent creation when response_format is provided as a mapping."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent")

    mock_agent = MagicMock()
    mock_agent.name = "test-agent"
    mock_agent.version = "1.0"
    mock_project_client.agents.create_version = AsyncMock(return_value=mock_agent)

    runtime_schema = {
        "title": "WeatherDigest",
        "type": "object",
        "properties": {
            "location": {"type": "string"},
            "conditions": {"type": "string"},
            "temperature_c": {"type": "number"},
            "advisory": {"type": "string"},
        },
        "required": ["location", "conditions", "temperature_c", "advisory"],
        "additionalProperties": False,
    }

    run_options = {"model": "test-model"}
    response_format_mapping = {
        "type": "json_schema",
        "json_schema": {
            "name": runtime_schema["title"],
            "strict": True,
            "schema": runtime_schema,
        },
    }
    chat_options = {"response_format": response_format_mapping}

    await client._get_agent_reference_or_create(run_options, None, chat_options)

    call_args = mock_project_client.agents.create_version.call_args
    created_definition = call_args[1]["definition"]

    assert hasattr(created_definition, "text")
    assert created_definition.text is not None
    format_config = created_definition.text.format
    assert isinstance(format_config, TextResponseFormatJsonSchema)
    assert format_config.name == runtime_schema["title"]
    assert format_config.schema == runtime_schema
    assert format_config.strict is True


async def test_runtime_structured_output_override_logs_warning(
    mock_project_client: MagicMock,
) -> None:
    """Test warning is logged when runtime structured_output differs from creation-time configuration."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent")

    mock_agent = MagicMock()
    mock_agent.name = "test-agent"
    mock_agent.version = "1.0"
    mock_project_client.agents.create_version = AsyncMock(return_value=mock_agent)
    messages = [Message(role="user", contents=[Content.from_text(text="Hello")])]

    with patch(
        "agent_framework_openai._chat_client.RawOpenAIChatClient._prepare_options",
        return_value={"model": "test-model"},
    ):
        await client._prepare_options(messages, {"response_format": ResponseFormatModel})

    with (
        patch(
            "agent_framework_openai._chat_client.RawOpenAIChatClient._prepare_options",
            return_value={"model": "test-model"},
        ),
        patch("agent_framework_azure_ai._client.logger.warning") as mock_warning,
    ):
        await client._prepare_options(messages, {"response_format": AlternateResponseFormatModel})
    mock_warning.assert_called_once()
    assert "Use AzureOpenAIResponsesClient instead." in mock_warning.call_args[0][0]


async def test_prepare_options_excludes_response_format(
    mock_project_client: MagicMock,
) -> None:
    """Test that prepare_options excludes response_format, text, and text_format from final run options."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent", agent_version="1.0")

    messages = [Message(role="user", contents=[Content.from_text(text="Hello")])]
    chat_options: ChatOptions = {}

    with (
        patch(
            "agent_framework_openai._chat_client.RawOpenAIChatClient._prepare_options",
            return_value={
                "model": "test-model",
                "response_format": ResponseFormatModel,
                "text": {"format": {"type": "json_schema", "name": "test"}},
                "text_format": ResponseFormatModel,
            },
        ),
        patch.object(
            client,
            "_get_agent_reference_or_create",
            return_value={"name": "test-agent", "version": "1.0", "type": "agent_reference"},
        ),
    ):
        run_options = await client._prepare_options(messages, chat_options)

        # response_format, text, and text_format should be excluded from final run options
        # because they are configured at agent level, not request level
        assert "response_format" not in run_options
        assert "text" not in run_options
        assert "text_format" not in run_options
        # But extra_body should contain agent reference
        assert "extra_body" in run_options
        assert run_options["extra_body"]["agent_reference"]["name"] == "test-agent"


async def test_prepare_options_keeps_values_for_unsupported_option_keys(
    mock_project_client: MagicMock,
) -> None:
    """Test that run_options removal only applies to known AzureAI agent-level option mappings."""
    client = create_test_azure_ai_client(mock_project_client, agent_name="test-agent", agent_version="1.0")
    messages = [Message(role="user", contents=[Content.from_text(text="Hello")])]

    with (
        patch(
            "agent_framework_openai._chat_client.RawOpenAIChatClient._prepare_options",
            return_value={
                "model": "test-model",
                "tools": [{"type": "function", "name": "weather"}],
                "text": {"format": {"type": "json_schema", "name": "schema"}},
                "text_format": ResponseFormatModel,
                "custom_option": "keep-me",
            },
        ),
        patch.object(
            client,
            "_get_agent_reference_or_create",
            return_value={"name": "test-agent", "version": "1.0", "type": "agent_reference"},
        ),
    ):
        run_options = await client._prepare_options(messages, {})

        assert "model" not in run_options
        assert "tools" not in run_options
        assert "text" not in run_options
        assert "text_format" not in run_options
        assert run_options["custom_option"] == "keep-me"


def test_get_conversation_id_with_store_true_and_conversation_id() -> None:
    """Test _get_conversation_id returns conversation ID when store is True and conversation exists."""
    client = create_test_azure_ai_client(MagicMock())

    # Mock OpenAI response with conversation
    mock_response = MagicMock(spec=OpenAIResponse)
    mock_response.id = "resp_12345"
    mock_conversation = MagicMock()
    mock_conversation.id = "conv_67890"
    mock_response.conversation = mock_conversation

    result = client._get_conversation_id(mock_response, store=True)

    assert result == "conv_67890"


def test_get_conversation_id_with_store_true_and_no_conversation() -> None:
    """Test _get_conversation_id returns response ID when store is True and no conversation exists."""
    client = create_test_azure_ai_client(MagicMock())

    # Mock OpenAI response without conversation
    mock_response = MagicMock(spec=OpenAIResponse)
    mock_response.id = "resp_12345"
    mock_response.conversation = None

    result = client._get_conversation_id(mock_response, store=True)

    assert result == "resp_12345"


def test_get_conversation_id_with_store_true_and_empty_conversation_id() -> None:
    """Test _get_conversation_id returns response ID when store is True and conversation ID is empty."""
    client = create_test_azure_ai_client(MagicMock())

    # Mock OpenAI response with conversation but empty ID
    mock_response = MagicMock(spec=OpenAIResponse)
    mock_response.id = "resp_12345"
    mock_conversation = MagicMock()
    mock_conversation.id = ""
    mock_response.conversation = mock_conversation

    result = client._get_conversation_id(mock_response, store=True)

    assert result == "resp_12345"


def test_get_conversation_id_with_store_false() -> None:
    """Test _get_conversation_id returns None when store is False."""
    client = create_test_azure_ai_client(MagicMock())

    # Mock OpenAI response with conversation
    mock_response = MagicMock(spec=OpenAIResponse)
    mock_response.id = "resp_12345"
    mock_conversation = MagicMock()
    mock_conversation.id = "conv_67890"
    mock_response.conversation = mock_conversation

    result = client._get_conversation_id(mock_response, store=False)

    assert result is None


def test_get_conversation_id_with_parsed_response_and_store_true() -> None:
    """Test _get_conversation_id works with ParsedResponse when store is True."""
    client = create_test_azure_ai_client(MagicMock())

    # Mock ParsedResponse with conversation
    mock_response = MagicMock(spec=ParsedResponse[BaseModel])
    mock_response.id = "resp_parsed_12345"
    mock_conversation = MagicMock()
    mock_conversation.id = "conv_parsed_67890"
    mock_response.conversation = mock_conversation

    result = client._get_conversation_id(mock_response, store=True)

    assert result == "conv_parsed_67890"


def test_get_conversation_id_with_parsed_response_no_conversation() -> None:
    """Test _get_conversation_id returns response ID with ParsedResponse when no conversation exists."""
    client = create_test_azure_ai_client(MagicMock())

    # Mock ParsedResponse without conversation
    mock_response = MagicMock(spec=ParsedResponse[BaseModel])
    mock_response.id = "resp_parsed_12345"
    mock_response.conversation = None

    result = client._get_conversation_id(mock_response, store=True)

    assert result == "resp_parsed_12345"


# region MCP Tool Dict Tests
# These tests verify that dict-based MCP tools are processed correctly by from_azure_ai_tools


def test_from_azure_ai_tools_mcp() -> None:
    """Test from_azure_ai_tools with MCP tool."""
    mcp_tool = MCPTool(server_label="test_server", server_url="http://localhost:8080")
    parsed_tools = from_azure_ai_tools([mcp_tool])
    assert len(parsed_tools) == 1
    assert parsed_tools[0]["type"] == "mcp"
    assert parsed_tools[0]["server_label"] == "test_server"
    assert parsed_tools[0]["server_url"] == "http://localhost:8080"


def test_from_azure_ai_tools_code_interpreter() -> None:
    """Test from_azure_ai_tools with Code Interpreter tool."""
    ci_tool = CodeInterpreterTool(container=AutoCodeInterpreterToolParam(file_ids=["file-1"]))
    parsed_tools = from_azure_ai_tools([ci_tool])
    assert len(parsed_tools) == 1
    assert parsed_tools[0]["type"] == "code_interpreter"


def test_from_azure_ai_tools_file_search() -> None:
    """Test from_azure_ai_tools with File Search tool."""
    fs_tool = FileSearchTool(vector_store_ids=["vs-1"], max_num_results=5)
    parsed_tools = from_azure_ai_tools([fs_tool])
    assert len(parsed_tools) == 1
    assert parsed_tools[0]["type"] == "file_search"
    assert parsed_tools[0]["vector_store_ids"] == ["vs-1"]
    assert parsed_tools[0]["max_num_results"] == 5


def test_from_azure_ai_tools_web_search() -> None:
    """Test from_azure_ai_tools with Web Search tool."""
    ws_tool = WebSearchPreviewTool(
        user_location=ApproximateLocation(city="Seattle", country="US", region="WA", timezone="PST")
    )
    parsed_tools = from_azure_ai_tools([ws_tool])
    assert len(parsed_tools) == 1
    assert parsed_tools[0]["type"] == "web_search_preview"
    assert parsed_tools[0]["user_location"]["city"] == "Seattle"


# endregion

# region Integration Tests


@tool(approval_mode="never_require")
def get_weather(
    location: Annotated[str, Field(description="The location to get the weather for.")],
) -> str:
    """Get the weather for a given location."""
    return f"The weather in {location} is sunny with a high of 25°C."


class OutputStruct(BaseModel):
    """A structured output for testing purposes."""

    location: str
    weather: str


@fixture
async def client() -> AsyncGenerator[AzureAIClient, None]:
    """Create a client to test with."""
    agent_name = f"test-agent-{uuid4()}"
    endpoint = os.environ["AZURE_AI_PROJECT_ENDPOINT"]
    async with (
        AzureCliCredential() as credential,
        AIProjectClient(endpoint=endpoint, credential=credential) as project_client,
    ):
        client = AzureAIClient(
            project_client=project_client,
            agent_name=agent_name,
        )
        try:
            assert client.function_invocation_configuration
            # Need at least 2 iterations for tool_choice tests: one to get function call, one to get final response
            client.function_invocation_configuration["max_iterations"] = 2
            yield client
        finally:
            await project_client.agents.delete(agent_name=agent_name)


# region Factory Method Tests


def test_get_code_interpreter_tool_basic() -> None:
    """Test get_code_interpreter_tool returns CodeInterpreterTool."""
    tool = AzureAIClient.get_code_interpreter_tool()
    assert isinstance(tool, CodeInterpreterTool)


def test_get_code_interpreter_tool_with_file_ids() -> None:
    """Test get_code_interpreter_tool with file_ids."""
    tool = AzureAIClient.get_code_interpreter_tool(file_ids=["file-123", "file-456"])
    assert isinstance(tool, CodeInterpreterTool)
    assert tool["container"]["file_ids"] == ["file-123", "file-456"]


def test_get_code_interpreter_tool_with_content() -> None:
    """Test get_code_interpreter_tool accepts Content.from_hosted_file in file_ids."""
    from agent_framework import Content

    content = Content.from_hosted_file("file-content-123")
    tool = AzureAIClient.get_code_interpreter_tool(file_ids=[content])
    assert isinstance(tool, CodeInterpreterTool)
    assert tool["container"]["file_ids"] == ["file-content-123"]


def test_get_code_interpreter_tool_with_mixed_file_ids() -> None:
    """Test get_code_interpreter_tool accepts a mix of strings and Content objects."""
    from agent_framework import Content

    content = Content.from_hosted_file("file-from-content")
    tool = AzureAIClient.get_code_interpreter_tool(file_ids=["file-plain", content])
    assert isinstance(tool, CodeInterpreterTool)
    assert sorted(tool["container"]["file_ids"]) == ["file-from-content", "file-plain"]


def test_get_code_interpreter_tool_content_unsupported_type() -> None:
    """Test get_code_interpreter_tool raises ValueError for unsupported Content types."""
    from agent_framework import Content

    content = Content.from_hosted_vector_store("vs-123")
    with pytest.raises(ValueError, match="Unsupported Content type"):
        AzureAIClient.get_code_interpreter_tool(file_ids=[content])


def test_get_file_search_tool_basic() -> None:
    """Test get_file_search_tool returns FileSearchTool."""
    tool = AzureAIClient.get_file_search_tool(vector_store_ids=["vs-123"])
    assert isinstance(tool, FileSearchTool)
    assert tool["vector_store_ids"] == ["vs-123"]


def test_get_file_search_tool_with_options() -> None:
    """Test get_file_search_tool with max_num_results."""
    tool = AzureAIClient.get_file_search_tool(
        vector_store_ids=["vs-123"],
        max_num_results=10,
    )
    assert isinstance(tool, FileSearchTool)
    assert tool["max_num_results"] == 10


def test_get_file_search_tool_requires_vector_store_ids() -> None:
    """Test get_file_search_tool raises ValueError when vector_store_ids is empty."""
    with pytest.raises(ValueError, match="vector_store_ids"):
        AzureAIClient.get_file_search_tool(vector_store_ids=[])


def test_get_web_search_tool_basic() -> None:
    """Test get_web_search_tool returns WebSearchPreviewTool."""
    tool = AzureAIClient.get_web_search_tool()
    assert isinstance(tool, WebSearchPreviewTool)


def test_get_web_search_tool_with_location() -> None:
    """Test get_web_search_tool with user_location."""
    tool = AzureAIClient.get_web_search_tool(
        user_location={"city": "Seattle", "country": "US"},
    )
    assert isinstance(tool, WebSearchPreviewTool)
    assert tool.user_location is not None
    assert tool.user_location.city == "Seattle"
    assert tool.user_location.country == "US"


def test_get_web_search_tool_with_search_context_size() -> None:
    """Test get_web_search_tool with search_context_size."""
    tool = AzureAIClient.get_web_search_tool(search_context_size="high")
    assert isinstance(tool, WebSearchPreviewTool)
    assert tool.search_context_size == "high"


def test_get_mcp_tool_basic() -> None:
    """Test get_mcp_tool returns MCPTool."""
    tool = AzureAIClient.get_mcp_tool(name="test_mcp", url="https://example.com")
    assert isinstance(tool, MCPTool)
    assert tool["server_label"] == "test_mcp"
    assert tool["server_url"] == "https://example.com"


def test_get_mcp_tool_with_description() -> None:
    """Test get_mcp_tool with description."""
    tool = AzureAIClient.get_mcp_tool(
        name="test_mcp",
        url="https://example.com",
        description="Test MCP server",
    )
    assert tool["server_description"] == "Test MCP server"


def test_get_mcp_tool_with_project_connection_id() -> None:
    """Test get_mcp_tool with project_connection_id."""
    tool = AzureAIClient.get_mcp_tool(
        name="test_mcp",
        project_connection_id="conn-123",
    )
    assert tool["project_connection_id"] == "conn-123"


def test_get_image_generation_tool_basic() -> None:
    """Test get_image_generation_tool returns ImageGenTool."""
    tool = AzureAIClient.get_image_generation_tool()
    assert isinstance(tool, ImageGenTool)


def test_get_image_generation_tool_with_options() -> None:
    """Test get_image_generation_tool with various options."""
    tool = AzureAIClient.get_image_generation_tool(
        size="1024x1024",
        quality="high",
        output_format="png",
    )
    assert isinstance(tool, ImageGenTool)
    assert tool["size"] == "1024x1024"
    assert tool["quality"] == "high"
    assert tool["output_format"] == "png"


# endregion


# region Azure AI Search Citation Enhancement Tests


def test_extract_azure_search_urls_with_dict_items(mock_project_client: MagicMock) -> None:
    """Test _extract_azure_search_urls with dict-style output (after JSON parsing)."""
    client = create_test_azure_ai_client(mock_project_client)
    mock_output = {
        "documents": [{"id": "1", "url": "https://search.example.com/"}],
        "get_urls": [
            "https://search.example.com/indexes/idx/docs/1?api-version=2024-07-01",
            "https://search.example.com/indexes/idx/docs/2?api-version=2024-07-01",
        ],
    }
    mock_search_item = MagicMock()
    mock_search_item.type = "azure_ai_search_call_output"
    mock_search_item.output = mock_output

    mock_call_item = MagicMock()
    mock_call_item.type = "azure_ai_search_call"

    mock_msg_item = MagicMock()
    mock_msg_item.type = "message"

    urls = client._extract_azure_search_urls([mock_call_item, mock_search_item, mock_msg_item])
    assert len(urls) == 2
    assert urls[0] == "https://search.example.com/indexes/idx/docs/1?api-version=2024-07-01"
    assert urls[1] == "https://search.example.com/indexes/idx/docs/2?api-version=2024-07-01"


def test_extract_azure_search_urls_with_object_items(mock_project_client: MagicMock) -> None:
    """Test _extract_azure_search_urls with object-style output items."""
    client = create_test_azure_ai_client(mock_project_client)
    mock_output = MagicMock()
    mock_output.get_urls = ["https://example.com/doc/1", "https://example.com/doc/2"]
    mock_item = MagicMock()
    mock_item.type = "azure_ai_search_call_output"
    mock_item.output = mock_output

    urls = client._extract_azure_search_urls([mock_item])
    assert urls == ["https://example.com/doc/1", "https://example.com/doc/2"]


def test_extract_azure_search_urls_no_search_items(mock_project_client: MagicMock) -> None:
    """Test _extract_azure_search_urls with no search output items."""
    client = create_test_azure_ai_client(mock_project_client)
    mock_item = MagicMock()
    mock_item.type = "message"
    urls = client._extract_azure_search_urls([mock_item])
    assert urls == []


def test_extract_azure_search_urls_with_json_string_output(mock_project_client: MagicMock) -> None:
    """Test _extract_azure_search_urls with JSON string output (non-streaming pydantic extra field)."""
    client = create_test_azure_ai_client(mock_project_client)
    json_output = json.dumps({
        "documents": [{"id": "1"}],
        "get_urls": [
            "https://search.example.com/indexes/idx/docs/1?api-version=2024-07-01",
        ],
    })
    mock_item = MagicMock()
    mock_item.type = "azure_ai_search_call_output"
    mock_item.output = json_output

    urls = client._extract_azure_search_urls([mock_item])
    assert len(urls) == 1
    assert urls[0] == "https://search.example.com/indexes/idx/docs/1?api-version=2024-07-01"


def test_get_search_doc_url_valid(mock_project_client: MagicMock) -> None:
    """Test _get_search_doc_url with valid doc_N title."""
    client = create_test_azure_ai_client(mock_project_client)
    get_urls = ["https://example.com/doc/0", "https://example.com/doc/1", "https://example.com/doc/2"]

    assert client._get_search_doc_url("doc_0", get_urls) == "https://example.com/doc/0"
    assert client._get_search_doc_url("doc_1", get_urls) == "https://example.com/doc/1"
    assert client._get_search_doc_url("doc_2", get_urls) == "https://example.com/doc/2"


def test_get_search_doc_url_out_of_range(mock_project_client: MagicMock) -> None:
    """Test _get_search_doc_url with out-of-range index."""
    client = create_test_azure_ai_client(mock_project_client)
    get_urls = ["https://example.com/doc/0"]
    assert client._get_search_doc_url("doc_5", get_urls) is None


def test_get_search_doc_url_no_match(mock_project_client: MagicMock) -> None:
    """Test _get_search_doc_url with non-matching title."""
    client = create_test_azure_ai_client(mock_project_client)
    get_urls = ["https://example.com/doc/0"]
    assert client._get_search_doc_url("some_title", get_urls) is None
    assert client._get_search_doc_url(None, get_urls) is None
    assert client._get_search_doc_url("doc_0", []) is None


def test_enrich_annotations_with_search_urls(mock_project_client: MagicMock) -> None:
    """Test _enrich_annotations_with_search_urls enriches citation annotations."""
    client = create_test_azure_ai_client(mock_project_client)
    get_urls = [
        "https://search.example.com/indexes/idx/docs/16?api-version=2024-07-01",
        "https://search.example.com/indexes/idx/docs/41?api-version=2024-07-01",
    ]

    content = Content.from_text(text="test response")
    content.annotations = [
        {
            "type": "citation",
            "title": "doc_0",
            "url": "https://search.example.com/",
        },
        {
            "type": "citation",
            "title": "doc_1",
            "url": "https://search.example.com/",
        },
    ]

    client._enrich_annotations_with_search_urls([content], get_urls)

    assert content.annotations[0]["additional_properties"]["get_url"] == get_urls[0]
    assert content.annotations[1]["additional_properties"]["get_url"] == get_urls[1]


def test_enrich_annotations_no_match(mock_project_client: MagicMock) -> None:
    """Test _enrich_annotations_with_search_urls with non-matching titles."""
    client = create_test_azure_ai_client(mock_project_client)
    get_urls = ["https://search.example.com/indexes/idx/docs/16?api-version=2024-07-01"]

    content = Content.from_text(text="test response")
    content.annotations = [
        {
            "type": "citation",
            "title": "some_title",
            "url": "https://search.example.com/",
        },
    ]

    client._enrich_annotations_with_search_urls([content], get_urls)
    assert "additional_properties" not in content.annotations[0] or "get_url" not in content.annotations[0].get(
        "additional_properties", {}
    )


def test_enrich_annotations_empty_get_urls(mock_project_client: MagicMock) -> None:
    """Test _enrich_annotations_with_search_urls with empty get_urls."""
    client = create_test_azure_ai_client(mock_project_client)
    content = Content.from_text(text="test")
    content.annotations = [{"type": "citation", "title": "doc_0", "url": "https://example.com/"}]

    # Should not raise or modify
    client._enrich_annotations_with_search_urls([content], [])
    assert "additional_properties" not in content.annotations[0]


async def test_inner_get_response_enriches_non_streaming(mock_project_client: MagicMock) -> None:
    """Test _inner_get_response enriches url_citation annotations for non-streaming responses."""
    client = create_test_azure_ai_client(mock_project_client)

    # Build a ChatResponse with citation annotations and a raw_representation carrying search output
    content = Content.from_text(text="Here is the result【5:0†source】.")
    content.annotations = [
        Annotation(type="citation", title="doc_0", url="https://search.example.com/"),
    ]
    msg = Message(role="assistant", contents=[content])
    mock_raw = MagicMock()
    mock_search_output = MagicMock()
    mock_search_output.type = "azure_ai_search_call_output"
    mock_search_output_data = MagicMock()
    mock_search_output_data.get_urls = [
        "https://search.example.com/indexes/idx/docs/16?api-version=2024-07-01",
    ]
    mock_search_output.output = mock_search_output_data
    mock_raw.output = [mock_search_output]

    base_response = ChatResponse(messages=[msg], raw_representation=mock_raw)

    async def _fake_awaitable() -> ChatResponse:
        return base_response

    with patch.object(RawOpenAIChatClient, "_inner_get_response", return_value=_fake_awaitable()):
        result_awaitable = client._inner_get_response(messages=[], options={}, stream=False)
        result = await result_awaitable  # type: ignore[misc]

    ann = result.messages[0].contents[0].annotations[0]
    assert ann["additional_properties"]["get_url"] == (
        "https://search.example.com/indexes/idx/docs/16?api-version=2024-07-01"
    )


async def test_inner_get_response_no_search_output_non_streaming(mock_project_client: MagicMock) -> None:
    """Test _inner_get_response passes through when no search output exists."""
    client = create_test_azure_ai_client(mock_project_client)

    content = Content.from_text(text="Hello world")
    msg = Message(role="assistant", contents=[content])
    mock_raw = MagicMock()
    mock_raw.output = []
    base_response = ChatResponse(messages=[msg], raw_representation=mock_raw)

    async def _fake_awaitable() -> ChatResponse:
        return base_response

    with patch.object(RawOpenAIChatClient, "_inner_get_response", return_value=_fake_awaitable()):
        result_awaitable = client._inner_get_response(messages=[], options={}, stream=False)
        result = await result_awaitable  # type: ignore[misc]

    assert result.messages[0].contents[0].text == "Hello world"


def _create_mock_stream() -> MagicMock:
    """Create a mock ResponseStream with working with_transform_hook."""
    mock_stream = MagicMock(spec=ResponseStream)
    mock_stream._transform_hooks = []
    mock_stream.with_transform_hook.side_effect = lambda hook: mock_stream._transform_hooks.append(hook) or mock_stream
    return mock_stream


def test_inner_get_response_streaming_registers_hook(mock_project_client: MagicMock) -> None:
    """Test _inner_get_response appends a transform hook to the stream for streaming responses."""
    client = create_test_azure_ai_client(mock_project_client)

    mock_stream = _create_mock_stream()

    with patch.object(RawOpenAIChatClient, "_inner_get_response", return_value=mock_stream):
        result = client._inner_get_response(messages=[], options={}, stream=True)

    assert result is mock_stream
    assert len(mock_stream._transform_hooks) == 1


def test_streaming_hook_captures_search_urls(mock_project_client: MagicMock) -> None:
    """Test the streaming transform hook captures get_urls from search output events."""
    client = create_test_azure_ai_client(mock_project_client)

    mock_stream = _create_mock_stream()

    with patch.object(RawOpenAIChatClient, "_inner_get_response", return_value=mock_stream):
        client._inner_get_response(messages=[], options={}, stream=True)

    hook = mock_stream._transform_hooks[0]

    # Simulate azure_ai_search_call_output event
    mock_item = MagicMock()
    mock_item.type = "azure_ai_search_call_output"
    mock_item.output = MagicMock()
    mock_item.output.get_urls = [
        "https://search.example.com/indexes/idx/docs/16?api-version=2024-07-01",
    ]

    raw_event = MagicMock()
    raw_event.type = "response.output_item.added"
    raw_event.item = mock_item

    update = ChatResponseUpdate(raw_representation=raw_event)
    result = hook(update)
    assert result is update  # passes through (no annotations to enrich)


def test_streaming_hook_enriches_url_citation(mock_project_client: MagicMock) -> None:
    """Test the streaming transform hook enriches url_citation annotations with get_urls."""
    client = create_test_azure_ai_client(mock_project_client)

    mock_stream = _create_mock_stream()

    with patch.object(RawOpenAIChatClient, "_inner_get_response", return_value=mock_stream):
        client._inner_get_response(messages=[], options={}, stream=True)

    hook = mock_stream._transform_hooks[0]

    # Step 1: Feed search output event to capture URLs
    mock_item = MagicMock()
    mock_item.type = "azure_ai_search_call_output"
    mock_item.output = MagicMock()
    mock_item.output.get_urls = [
        "https://search.example.com/indexes/idx/docs/16?api-version=2024-07-01",
        "https://search.example.com/indexes/idx/docs/41?api-version=2024-07-01",
    ]
    raw_output_event = MagicMock()
    raw_output_event.type = "response.output_item.added"
    raw_output_event.item = mock_item
    hook(ChatResponseUpdate(raw_representation=raw_output_event))

    # Step 2: Feed url_citation annotation event (annotation is always a dict in streaming)
    raw_ann_event = MagicMock()
    raw_ann_event.type = "response.output_text.annotation.added"
    raw_ann_event.annotation = {
        "type": "url_citation",
        "title": "doc_0",
        "url": "https://search.example.com/",
        "start_index": 100,
        "end_index": 112,
    }
    raw_ann_event.annotation_index = 0

    result = hook(ChatResponseUpdate(raw_representation=raw_ann_event))

    # Verify the result has enriched annotation
    assert result.contents is not None
    found = False
    for content_item in result.contents:
        if hasattr(content_item, "annotations") and content_item.annotations:
            for ann in content_item.annotations:
                if isinstance(ann, dict) and ann.get("title") == "doc_0":
                    found = True
                    assert ann["additional_properties"]["get_url"] == (
                        "https://search.example.com/indexes/idx/docs/16?api-version=2024-07-01"
                    )
    assert found, "Expected url_citation annotation with enriched get_url"


def test_build_url_citation_content(mock_project_client: MagicMock) -> None:
    """Test _build_url_citation_content creates Content with enriched Annotation."""
    client = create_test_azure_ai_client(mock_project_client)
    get_urls = ["https://search.example.com/indexes/idx/docs/16?api-version=2024-07-01"]

    annotation_data = {
        "type": "url_citation",
        "title": "doc_0",
        "url": "https://search.example.com/",
        "start_index": 100,
        "end_index": 112,
    }

    raw_event = MagicMock()
    raw_event.annotation_index = 0

    content = client._build_url_citation_content(annotation_data, get_urls, raw_event)

    assert content.annotations is not None
    ann = content.annotations[0]
    assert ann["type"] == "citation"
    assert ann["title"] == "doc_0"
    assert ann["url"] == "https://search.example.com/"
    assert ann["additional_properties"]["get_url"] == get_urls[0]
    assert ann["annotated_regions"][0]["start_index"] == 100
    assert ann["annotated_regions"][0]["end_index"] == 112


def test_build_url_citation_content_with_dict(mock_project_client: MagicMock) -> None:
    """Test _build_url_citation_content handles dict-style annotation data."""
    client = create_test_azure_ai_client(mock_project_client)
    get_urls = ["https://search.example.com/indexes/idx/docs/16?api-version=2024-07-01"]

    annotation_data = {
        "type": "url_citation",
        "title": "doc_1",
        "url": "https://search.example.com/",
        "start_index": 200,
        "end_index": 215,
    }

    raw_event = MagicMock()
    raw_event.annotation_index = 1

    content = client._build_url_citation_content(annotation_data, get_urls, raw_event)

    assert content.annotations is not None
    ann = content.annotations[0]
    assert ann["type"] == "citation"
    assert ann["title"] == "doc_1"
    # doc_1 is out of range for a 1-element get_urls, so no get_url
    assert "get_url" not in ann.get("additional_properties", {})


# region OAuth Consent


def test_parse_chunk_with_oauth_consent_request(mock_project_client: MagicMock) -> None:
    """Test that a streaming oauth_consent_request output item is parsed into oauth_consent_request content.

    This reproduces the bug from issue #3950 where the event was logged as "Unparsed event"
    and silently discarded, causing the agent run to complete with zero content.
    """
    client = AzureAIClient(project_client=mock_project_client, agent_name="test")
    chat_options: dict[str, Any] = {}
    function_call_ids: dict[int, tuple[str, str]] = {}

    mock_item = MagicMock()
    mock_item.type = "oauth_consent_request"
    mock_item.consent_link = "https://login.microsoftonline.com/common/oauth2/authorize?client_id=abc123"

    mock_event = MagicMock()
    mock_event.type = "response.output_item.added"
    mock_event.item = mock_item
    mock_event.output_index = 0

    update = client._parse_chunk_from_openai(mock_event, chat_options, function_call_ids)

    assert len(update.contents) == 1
    consent_content = update.contents[0]
    assert consent_content.type == "oauth_consent_request"
    assert consent_content.consent_link == "https://login.microsoftonline.com/common/oauth2/authorize?client_id=abc123"
    assert consent_content.user_input_request is True


def test_parse_response_with_oauth_consent_output_item(mock_project_client: MagicMock) -> None:
    """Test that a non-streaming oauth_consent_request output item is parsed correctly."""
    client = AzureAIClient(project_client=mock_project_client, agent_name="test")

    mock_item = MagicMock()
    mock_item.type = "oauth_consent_request"
    mock_item.consent_link = "https://login.microsoftonline.com/consent?code=abc"

    mock_response = MagicMock()
    mock_response.output = [mock_item]
    mock_response.output_parsed = None
    mock_response.metadata = {}
    mock_response.id = "resp-oauth-1"
    mock_response.model = "test-model"
    mock_response.created_at = 1000000000
    mock_response.usage = None
    mock_response.status = "completed"

    response = client._parse_response_from_openai(mock_response, {})

    assert len(response.messages) > 0
    consent_contents = [c for c in response.messages[0].contents if c.type == "oauth_consent_request"]
    assert len(consent_contents) == 1
    assert consent_contents[0].consent_link == "https://login.microsoftonline.com/consent?code=abc"


def test_parse_chunk_oauth_consent_no_link(mock_project_client: MagicMock) -> None:
    """Test that a streaming oauth_consent_request with no consent_link produces empty contents."""
    client = AzureAIClient(project_client=mock_project_client, agent_name="test")

    mock_item = MagicMock()
    mock_item.type = "oauth_consent_request"
    mock_item.consent_link = ""

    mock_event = MagicMock()
    mock_event.type = "response.output_item.added"
    mock_event.item = mock_item
    mock_event.output_index = 0

    update = client._parse_chunk_from_openai(mock_event, {}, {})

    assert not any(c.type == "oauth_consent_request" for c in update.contents)


def test_parse_response_oauth_consent_no_link(mock_project_client: MagicMock) -> None:
    """Test that a non-streaming oauth_consent_request with no consent_link appends no content."""
    client = AzureAIClient(project_client=mock_project_client, agent_name="test")

    mock_item = MagicMock()
    mock_item.type = "oauth_consent_request"
    mock_item.consent_link = None

    mock_response = MagicMock()
    mock_response.output = [mock_item]
    mock_response.output_parsed = None
    mock_response.metadata = {}
    mock_response.id = "resp-oauth-2"
    mock_response.model = "test-model"
    mock_response.created_at = 1000000000
    mock_response.usage = None
    mock_response.status = "completed"

    response = client._parse_response_from_openai(mock_response, {})

    consent_contents = [c for c in response.messages[0].contents if c.type == "oauth_consent_request"]
    assert len(consent_contents) == 0


# endregion