From 856b8770e1a4b6db45235927a7940060d6feaf0a Mon Sep 17 00:00:00 2001
From: Sydney Runkle <sydneymarierunkle@gmail.com>
Date: Thu, 16 Oct 2025 23:44:30 -0400
Subject: [PATCH] initial skills middleware

---
 .../middleware/__init__.py                    |   8 +
 .../langchain_anthropic/middleware/skills.py  | 572 ++++++++++++++
 .../unit_tests/middleware/test_skills.py      | 744 ++++++++++++++++++
 libs/partners/anthropic/uv.lock               | 207 +++--
 4 files changed, 1414 insertions(+), 117 deletions(-)
 create mode 100644 libs/partners/anthropic/langchain_anthropic/middleware/skills.py
 create mode 100644 libs/partners/anthropic/tests/unit_tests/middleware/test_skills.py

diff --git a/libs/partners/anthropic/langchain_anthropic/middleware/__init__.py b/libs/partners/anthropic/langchain_anthropic/middleware/__init__.py
index d1a34993c8de0..f5716c766e00e 100644
--- a/libs/partners/anthropic/langchain_anthropic/middleware/__init__.py
+++ b/libs/partners/anthropic/langchain_anthropic/middleware/__init__.py
@@ -13,12 +13,20 @@
 from langchain_anthropic.middleware.prompt_caching import (
     AnthropicPromptCachingMiddleware,
 )
+from langchain_anthropic.middleware.skills import (
+    ClaudeSkillsMiddleware,
+    LocalSkillConfig,
+    SkillConfig,
+)
 
 __all__ = [
     "AnthropicPromptCachingMiddleware",
     "ClaudeBashToolMiddleware",
+    "ClaudeSkillsMiddleware",
     "FilesystemClaudeMemoryMiddleware",
     "FilesystemClaudeTextEditorMiddleware",
+    "LocalSkillConfig",
+    "SkillConfig",
     "StateClaudeMemoryMiddleware",
     "StateClaudeTextEditorMiddleware",
     "StateFileSearchMiddleware",
diff --git a/libs/partners/anthropic/langchain_anthropic/middleware/skills.py b/libs/partners/anthropic/langchain_anthropic/middleware/skills.py
new file mode 100644
index 0000000000000..5c6f8365a5830
--- /dev/null
+++ b/libs/partners/anthropic/langchain_anthropic/middleware/skills.py
@@ -0,0 +1,572 @@
+"""Anthropic Skills middleware.
+
+Requires:
+    - langchain: For agent middleware framework
+    - langchain-anthropic: For ChatAnthropic model (already a dependency)
+"""
+
+import hashlib
+import os
+import zipfile
+from collections.abc import Awaitable, Callable
+from io import BytesIO
+from pathlib import Path
+from typing import Any, Literal
+from warnings import warn
+
+from langchain_anthropic.chat_models import ChatAnthropic
+
+try:
+    from langchain.agents.middleware.types import (
+        AgentMiddleware,
+        ModelCallResult,
+        ModelRequest,
+        ModelResponse,
+    )
+except ImportError as e:
+    msg = (
+        "ClaudeSkillsMiddleware requires 'langchain' to be installed. "
+        "This middleware is designed for use with LangChain agents. "
+        "Install it with: pip install langchain"
+    )
+    raise ImportError(msg) from e
+
+
+# Pre-built Anthropic skill IDs
+ANTHROPIC_SKILLS = {"pptx", "xlsx", "docx", "pdf"}
+
+# Required beta headers for Skills functionality
+REQUIRED_BETAS = [
+    "code-execution-2025-08-25",
+    "skills-2025-10-02",
+    "files-api-2025-04-14",
+]
+
+
+class SkillConfig:
+    """Configuration for a single skill.
+
+    Args:
+        skill_id: The skill identifier. For Anthropic pre-built skills, use
+            `'pptx'`, `'xlsx'`, `'docx'`, or `'pdf'`. For custom skills, use
+            the ID from the `/v1/skills` endpoint.
+        type: The skill type. `'anthropic'` for pre-built skills or `'custom'`
+            for user-uploaded skills.
+        version: The skill version. Use `'latest'` for the most recent version,
+            or specify a date-based version for Anthropic skills (e.g., `'20251002'`)
+            or epoch timestamp for custom skills.
+    """
+
+    def __init__(
+        self,
+        skill_id: str,
+        type: Literal["anthropic", "custom"] = "anthropic",  # noqa: A002
+        version: str = "latest",
+    ) -> None:
+        """Initialize skill configuration."""
+        self.skill_id = skill_id
+        self.type = type
+        self.version = version
+
+    def to_dict(self) -> dict[str, str]:
+        """Convert skill configuration to API format.
+
+        Returns:
+            Dictionary with skill configuration for API requests.
+        """
+        return {
+            "type": self.type,
+            "skill_id": self.skill_id,
+            "version": self.version,
+        }
+
+
+class LocalSkillConfig(SkillConfig):
+    """Configuration for a skill loaded from local files.
+
+    This class handles loading skills from the local filesystem and uploading
+    them to the Anthropic API. Skills are expected to be in a directory containing
+    a `SKILL.md` file with YAML frontmatter.
+
+    Args:
+        path: Path to the skill directory or zip file containing the skill.
+            The directory must contain a `SKILL.md` file with required frontmatter.
+        display_title: Optional display title for the skill when uploaded.
+            If not provided, the name from the SKILL.md frontmatter will be used.
+        auto_upload: If `True`, automatically upload the skill when the middleware
+            is initialized. If `False`, you must manually upload via the
+            `upload_skill` method.
+
+    Example:
+        ```python
+        from langchain_anthropic.middleware import (
+            ClaudeSkillsMiddleware,
+            LocalSkillConfig,
+        )
+
+        # Create middleware with local skill
+        middleware = ClaudeSkillsMiddleware(
+            skills=[
+                "pptx",  # Pre-built skill
+                LocalSkillConfig(path="./my-custom-skill"),  # Local skill
+            ]
+        )
+        ```
+    """
+
+    def __init__(
+        self,
+        path: str | Path,
+        *,
+        display_title: str | None = None,
+        auto_upload: bool = True,
+    ) -> None:
+        """Initialize local skill configuration.
+
+        Args:
+            path: Path to the skill directory or zip file.
+            display_title: Optional display title for the skill.
+            auto_upload: Whether to automatically upload the skill.
+
+        Raises:
+            FileNotFoundError: If the path does not exist.
+            ValueError: If the path is not a valid skill directory or zip file.
+        """
+        self.path = Path(path)
+        self.display_title = display_title
+        self.auto_upload = auto_upload
+        self._uploaded_skill_id: str | None = None
+        self._content_hash: str | None = None
+
+        # Validate path exists
+        if not self.path.exists():
+            msg = f"Skill path does not exist: {self.path}"
+            raise FileNotFoundError(msg)
+
+        # Validate it's a directory or zip file
+        if not (self.path.is_dir() or self.path.suffix == ".zip"):
+            msg = f"Skill path must be a directory or .zip file, got: {self.path}"
+            raise ValueError(msg)
+
+        # For directories, validate SKILL.md exists
+        if self.path.is_dir():
+            skill_md = self.path / "SKILL.md"
+            if not skill_md.exists():
+                msg = f"Skill directory must contain a SKILL.md file: {self.path}"
+                raise ValueError(msg)
+
+        # Initialize parent class with placeholder values
+        # These will be set after upload
+        super().__init__(
+            skill_id="",  # Will be set after upload
+            type="custom",
+            version="latest",
+        )
+
+    def _compute_content_hash(self) -> str:
+        """Compute a hash of the skill content for caching.
+
+        Returns:
+            SHA256 hash of the skill content.
+        """
+        hasher = hashlib.sha256()
+
+        if self.path.is_dir():
+            # Hash all files in the directory
+            for root, _dirs, files in os.walk(self.path):
+                for file in sorted(files):  # Sort for consistent hashing
+                    file_path = Path(root) / file
+                    hasher.update(str(file_path.relative_to(self.path)).encode())
+                    hasher.update(file_path.read_bytes())
+        else:
+            # Hash the zip file
+            hasher.update(self.path.read_bytes())
+
+        return hasher.hexdigest()
+
+    def _create_zip_bytes(self) -> bytes:
+        """Create a zip file from the skill directory or read existing zip.
+
+        The zip must contain a top-level folder with all files inside it,
+        as required by the Anthropic Skills API.
+
+        Returns:
+            Bytes of the zip file.
+        """
+        if self.path.suffix == ".zip":
+            return self.path.read_bytes()
+
+        # Create zip file in memory with top-level folder
+        # The directory name becomes the top-level folder in the zip
+        zip_buffer = BytesIO()
+
+        with zipfile.ZipFile(zip_buffer, "w", zipfile.ZIP_DEFLATED) as zip_file:
+            for root, _dirs, files in os.walk(self.path):
+                for file in files:
+                    file_path = Path(root) / file
+                    # Create path relative to parent, preserving directory name
+                    rel_path = file_path.relative_to(self.path.parent)
+                    zip_file.write(file_path, str(rel_path))
+
+        return zip_buffer.getvalue()
+
+    def upload_skill(self, client: Any) -> str:
+        """Upload the skill to Anthropic API.
+
+        Args:
+            client: Anthropic client instance.
+
+        Returns:
+            The uploaded skill ID.
+
+        Raises:
+            ValueError: If upload fails.
+        """
+        # Check if already uploaded with same content
+        content_hash = self._compute_content_hash()
+        if self._uploaded_skill_id and self._content_hash == content_hash:
+            return self._uploaded_skill_id
+
+        # Create zip file
+        zip_bytes = self._create_zip_bytes()
+
+        # Upload to Anthropic
+        try:
+            response = client.beta.skills.create(
+                files=[("skill.zip", zip_bytes, "application/zip")],
+                display_title=self.display_title,
+                betas=REQUIRED_BETAS,
+            )
+
+            # Store the skill ID and hash
+            self._uploaded_skill_id = response.id
+            self._content_hash = content_hash
+            self.skill_id = response.id
+
+            return response.id
+
+        except Exception as e:
+            msg = f"Failed to upload skill from {self.path}: {e}"
+            raise ValueError(msg) from e
+
+    @property
+    def is_uploaded(self) -> bool:
+        """Check if the skill has been uploaded.
+
+        Returns:
+            `True` if the skill has been uploaded, `False` otherwise.
+        """
+        return self._uploaded_skill_id is not None
+
+
+class ClaudeSkillsMiddleware(AgentMiddleware):
+    """Skills Middleware for Claude.
+
+    Enables Claude to use Skills - specialized capabilities for document processing,
+    data manipulation, and other domain-specific tasks. Skills are folders containing
+    instructions, scripts, and resources that Claude loads when relevant.
+
+    This middleware:
+
+    - Adds skills to model requests via the `container` parameter
+    - Injects required beta headers for Skills functionality
+    - Automatically adds code execution tool if not present (required for Skills)
+    - Supports both Anthropic pre-built skills and custom skills
+    - Handles uploading local skills to the Anthropic API
+
+    Requires both 'langchain' and 'langchain-anthropic' packages to be installed.
+
+    Learn more about Claude Skills
+    [here](https://docs.claude.com/en/docs/agents-and-tools/agent-skills/overview).
+
+    Example:
+        Basic usage with pre-built skills:
+
+        ```python
+        from langchain_anthropic.middleware import ClaudeSkillsMiddleware
+
+        # Enable PowerPoint and Excel skills
+        skills_middleware = ClaudeSkillsMiddleware(skills=["pptx", "xlsx"])
+
+        # Use with an agent
+        agent = create_react_agent(
+            model=ChatAnthropic(model="claude-sonnet-4-5-20250929"),
+            tools=[...],
+            middleware=[skills_middleware],
+        )
+        ```
+
+        Advanced usage with custom skills from API:
+
+        ```python
+        from langchain_anthropic.middleware import (
+            ClaudeSkillsMiddleware,
+            SkillConfig,
+        )
+
+        # Mix pre-built and custom skills
+        skills_middleware = ClaudeSkillsMiddleware(
+            skills=[
+                "pptx",  # Pre-built skill
+                SkillConfig(
+                    skill_id="custom-skill-123",
+                    type="custom",
+                    version="latest",
+                ),
+            ]
+        )
+        ```
+
+        Using local skill files:
+
+        ```python
+        from pathlib import Path
+        from langchain_anthropic.middleware import (
+            ClaudeSkillsMiddleware,
+            LocalSkillConfig,
+        )
+
+        # Load skill from local directory
+        skills_middleware = ClaudeSkillsMiddleware(
+            skills=[
+                "xlsx",  # Pre-built skill
+                LocalSkillConfig(
+                    path="./my-custom-skill",  # Directory with SKILL.md
+                    display_title="My Custom Skill",
+                    auto_upload=True,  # Automatically upload when first used
+                ),
+            ]
+        )
+        ```
+    """
+
+    def __init__(
+        self,
+        skills: list[str | SkillConfig | LocalSkillConfig],
+        unsupported_model_behavior: Literal["ignore", "warn", "raise"] = "warn",
+        code_execution_tool_name: str = "code_execution",
+    ) -> None:
+        """Initialize the middleware with skills configuration.
+
+        Args:
+            skills: List of skills to enable. Can be:
+                - Skill ID strings for Anthropic pre-built skills
+                  (`'pptx'`, `'xlsx'`, `'docx'`, `'pdf'`)
+                - `SkillConfig` objects for custom skills or fine-grained control
+                - `LocalSkillConfig` objects for skills loaded from local files
+            unsupported_model_behavior: Behavior when a non-Anthropic model is used.
+                - `'ignore'`: Skip skills injection silently
+                - `'warn'`: Log a warning and skip skills injection
+                - `'raise'`: Raise an error
+            code_execution_tool_name: Name of the code execution tool. If not present
+                in the request, it will be automatically added.
+
+        Raises:
+            ValueError: If more than 8 skills are provided (API limit) or if
+                invalid skill configuration is detected.
+        """
+        if len(skills) > 8:
+            msg = (
+                "Anthropic API supports a maximum of 8 skills per request, "
+                f"but {len(skills)} were provided."
+            )
+            raise ValueError(msg)
+
+        self.skills = self._normalize_skills(skills)
+        self.unsupported_model_behavior = unsupported_model_behavior
+        self.code_execution_tool_name = code_execution_tool_name
+
+    def _normalize_skills(
+        self, skills: list[str | SkillConfig | LocalSkillConfig]
+    ) -> list[SkillConfig | LocalSkillConfig]:
+        """Normalize skill configurations.
+
+        Args:
+            skills: List of skill IDs, SkillConfig objects, or LocalSkillConfig objects.
+
+        Returns:
+            List of SkillConfig or LocalSkillConfig objects.
+        """
+        normalized = []
+        for skill in skills:
+            if isinstance(skill, str):
+                # Infer type based on skill_id
+                skill_type: Literal["anthropic", "custom"] = (
+                    "anthropic" if skill in ANTHROPIC_SKILLS else "custom"
+                )
+                normalized.append(
+                    SkillConfig(skill_id=skill, type=skill_type, version="latest")
+                )
+            else:
+                normalized.append(skill)
+        return normalized
+
+    def _should_apply_skills(self, request: ModelRequest) -> bool:
+        """Check if skills should be applied to the request.
+
+        Args:
+            request: The model request to check.
+
+        Returns:
+            `True` if skills should be applied, `False` otherwise.
+
+        Raises:
+            ValueError: If model is unsupported and behavior is set to `'raise'`.
+        """
+        if not isinstance(request.model, ChatAnthropic):
+            msg = (
+                "ClaudeSkillsMiddleware only supports Anthropic models, "
+                f"not instances of {type(request.model)}"
+            )
+            if self.unsupported_model_behavior == "raise":
+                raise ValueError(msg)
+            if self.unsupported_model_behavior == "warn":
+                warn(msg, stacklevel=3)
+            return False
+
+        return True
+
+    def _ensure_code_execution_tool(self, request: ModelRequest) -> None:
+        """Ensure code execution tool is present in the request.
+
+        Skills require the code execution tool to be enabled. If not present,
+        this method will automatically add it.
+
+        Args:
+            request: The model request to check and modify.
+        """
+        tools = request.tools or []
+
+        # Check if code execution tool exists
+        has_code_execution = any(
+            (
+                isinstance(tool, dict)
+                and tool.get("name") == self.code_execution_tool_name
+            )
+            or (isinstance(tool, str) and tool == self.code_execution_tool_name)
+            or (hasattr(tool, "name") and tool.name == self.code_execution_tool_name)
+            for tool in tools
+        )
+
+        if not has_code_execution:
+            # Automatically add code execution tool
+            tools = list(tools)
+            tools.append(
+                {
+                    "type": "code_execution_20250825",
+                    "name": self.code_execution_tool_name,
+                }
+            )
+            request.tools = tools
+
+    def _upload_local_skills(self, request: ModelRequest) -> None:
+        """Upload any local skills that need uploading.
+
+        Args:
+            request: The model request to get Anthropic client from.
+
+        Raises:
+            ValueError: If upload fails or if model doesn't have a client.
+        """
+        # Check if there are any local skills that need uploading
+        has_local_skills = any(
+            isinstance(skill, LocalSkillConfig)
+            and skill.auto_upload
+            and not skill.is_uploaded
+            for skill in self.skills
+        )
+
+        if not has_local_skills:
+            return
+
+        # Get Anthropic client from the model
+        if not isinstance(request.model, ChatAnthropic):
+            return
+
+        # Get the underlying client
+        if not hasattr(request.model, "_client"):
+            msg = "ChatAnthropic model does not have a _client attribute"
+            raise ValueError(msg)
+
+        client = request.model._client  # noqa: SLF001
+
+        # Upload any local skills that need it
+        for skill in self.skills:
+            if (
+                isinstance(skill, LocalSkillConfig)
+                and skill.auto_upload
+                and not skill.is_uploaded
+            ):
+                skill.upload_skill(client)
+
+    def _inject_skills_config(self, request: ModelRequest) -> None:
+        """Inject skills configuration into the request.
+
+        Args:
+            request: The model request to modify.
+        """
+        # Add required beta headers
+        model_settings = request.model_settings or {}
+        existing_betas = model_settings.get("betas", [])
+
+        # Merge with required betas, avoiding duplicates
+        all_betas = list(set(existing_betas + REQUIRED_BETAS))
+        model_settings["betas"] = all_betas
+
+        # Create or update container configuration
+        container = model_settings.get("container", {})
+        container["skills"] = [skill.to_dict() for skill in self.skills]
+        model_settings["container"] = container
+
+        # Update request
+        request.model_settings = model_settings
+
+    def wrap_model_call(
+        self,
+        request: ModelRequest,
+        handler: Callable[[ModelRequest], ModelResponse],
+    ) -> ModelCallResult:
+        """Modify the model request to add skills configuration.
+
+        Args:
+            request: The model request to potentially modify.
+            handler: The handler to execute the model request.
+
+        Returns:
+            The model response from the handler.
+
+        Raises:
+            ValueError: If the model is unsupported and behavior is set to `'raise'`.
+        """
+        if not self._should_apply_skills(request):
+            return handler(request)
+
+        self._ensure_code_execution_tool(request)
+        self._upload_local_skills(request)
+        self._inject_skills_config(request)
+        return handler(request)
+
+    async def awrap_model_call(
+        self,
+        request: ModelRequest,
+        handler: Callable[[ModelRequest], Awaitable[ModelResponse]],
+    ) -> ModelCallResult:
+        """Modify the model request to add skills configuration (async version).
+
+        Args:
+            request: The model request to potentially modify.
+            handler: The async handler to execute the model request.
+
+        Returns:
+            The model response from the handler.
+
+        Raises:
+            ValueError: If the model is unsupported and behavior is set to `'raise'`.
+        """
+        if not self._should_apply_skills(request):
+            return await handler(request)
+
+        self._ensure_code_execution_tool(request)
+        self._upload_local_skills(request)
+        self._inject_skills_config(request)
+        return await handler(request)
diff --git a/libs/partners/anthropic/tests/unit_tests/middleware/test_skills.py b/libs/partners/anthropic/tests/unit_tests/middleware/test_skills.py
new file mode 100644
index 0000000000000..ec79482d629b0
--- /dev/null
+++ b/libs/partners/anthropic/tests/unit_tests/middleware/test_skills.py
@@ -0,0 +1,744 @@
+"""Tests for Anthropic Skills middleware."""
+
+import tempfile
+import warnings
+from pathlib import Path
+from typing import Any, cast
+from unittest.mock import MagicMock
+
+import pytest
+from langchain.agents.middleware.types import ModelRequest, ModelResponse
+from langchain_core.callbacks import (
+    AsyncCallbackManagerForLLMRun,
+    CallbackManagerForLLMRun,
+)
+from langchain_core.language_models import BaseChatModel
+from langchain_core.messages import AIMessage, BaseMessage, HumanMessage
+from langchain_core.outputs import ChatGeneration, ChatResult
+from langgraph.runtime import Runtime
+
+from langchain_anthropic.chat_models import ChatAnthropic
+from langchain_anthropic.middleware import (
+    ClaudeSkillsMiddleware,
+    LocalSkillConfig,
+    SkillConfig,
+)
+
+
+class FakeToolCallingModel(BaseChatModel):
+    """Fake model for testing middleware."""
+
+    def _generate(
+        self,
+        messages: list[BaseMessage],
+        stop: list[str] | None = None,
+        run_manager: CallbackManagerForLLMRun | None = None,
+        **kwargs: Any,
+    ) -> ChatResult:
+        """Top Level call"""
+        messages_string = "-".join([str(m.content) for m in messages])
+        message = AIMessage(content=messages_string, id="0")
+        return ChatResult(generations=[ChatGeneration(message=message)])
+
+    async def _agenerate(
+        self,
+        messages: list[BaseMessage],
+        stop: list[str] | None = None,
+        run_manager: AsyncCallbackManagerForLLMRun | None = None,
+        **kwargs: Any,
+    ) -> ChatResult:
+        """Async top level call"""
+        messages_string = "-".join([str(m.content) for m in messages])
+        message = AIMessage(content=messages_string, id="0")
+        return ChatResult(generations=[ChatGeneration(message=message)])
+
+    @property
+    def _llm_type(self) -> str:
+        return "fake-tool-call-model"
+
+
+def test_skill_config_initialization() -> None:
+    """Test SkillConfig initialization and to_dict method."""
+    # Test with default values (Anthropic skill)
+    skill = SkillConfig(skill_id="pptx")
+    assert skill.skill_id == "pptx"
+    assert skill.type == "anthropic"
+    assert skill.version == "latest"
+    assert skill.to_dict() == {
+        "type": "anthropic",
+        "skill_id": "pptx",
+        "version": "latest",
+    }
+
+    # Test with custom skill and specific version
+    skill = SkillConfig(
+        skill_id="custom-123",
+        type="custom",
+        version="1234567890",
+    )
+    assert skill.skill_id == "custom-123"
+    assert skill.type == "custom"
+    assert skill.version == "1234567890"
+    assert skill.to_dict() == {
+        "type": "custom",
+        "skill_id": "custom-123",
+        "version": "1234567890",
+    }
+
+
+def test_claude_skills_middleware_initialization() -> None:
+    """Test ClaudeSkillsMiddleware initialization."""
+    # Test with string skill IDs (Anthropic pre-built skills)
+    middleware = ClaudeSkillsMiddleware(skills=["pptx", "xlsx"])
+    assert len(middleware.skills) == 2
+    assert middleware.skills[0].skill_id == "pptx"
+    assert middleware.skills[0].type == "anthropic"
+    assert middleware.skills[1].skill_id == "xlsx"
+    assert middleware.skills[1].type == "anthropic"
+
+    # Test with SkillConfig objects
+    middleware = ClaudeSkillsMiddleware(
+        skills=[
+            SkillConfig(skill_id="pptx", type="anthropic", version="20251002"),
+            SkillConfig(skill_id="custom-123", type="custom", version="latest"),
+        ]
+    )
+    assert len(middleware.skills) == 2
+    assert middleware.skills[0].version == "20251002"
+    assert middleware.skills[1].type == "custom"
+
+    # Test with mixed skills
+    middleware = ClaudeSkillsMiddleware(
+        skills=[
+            "pptx",
+            SkillConfig(skill_id="custom-456", type="custom"),
+        ]
+    )
+    assert len(middleware.skills) == 2
+    assert middleware.skills[0].skill_id == "pptx"
+    assert middleware.skills[1].skill_id == "custom-456"
+
+
+def test_claude_skills_middleware_max_skills_validation() -> None:
+    """Test that ClaudeSkillsMiddleware validates maximum skill count."""
+    # Should raise error when more than 8 skills are provided
+    with pytest.raises(
+        ValueError,
+        match="Anthropic API supports a maximum of 8 skills per request",
+    ):
+        ClaudeSkillsMiddleware(skills=["pptx"] * 9)
+
+
+def test_claude_skills_middleware_code_execution_auto_added() -> None:
+    """Test that code execution tool is automatically added if missing."""
+    middleware = ClaudeSkillsMiddleware(skills=["pptx"])
+
+    mock_chat_anthropic = MagicMock(spec=ChatAnthropic)
+
+    # Request without code execution tool
+    fake_request = ModelRequest(
+        model=mock_chat_anthropic,
+        messages=[HumanMessage("Create a presentation")],
+        system_prompt=None,
+        tool_choice=None,
+        tools=[],  # No code execution tool initially
+        response_format=None,
+        state={"messages": [HumanMessage("Create a presentation")]},
+        runtime=cast(Runtime, object()),
+        model_settings={},
+    )
+
+    def mock_handler(req: ModelRequest) -> ModelResponse:
+        return ModelResponse(result=[AIMessage(content="mock response")])
+
+    # Should automatically add code_execution tool
+    result = middleware.wrap_model_call(fake_request, mock_handler)
+    assert isinstance(result, ModelResponse)
+
+    # Verify code_execution was added to tools
+    assert len(fake_request.tools) == 1
+    tool = fake_request.tools[0]
+    assert isinstance(tool, dict)
+    assert tool["name"] == "code_execution"
+    assert tool["type"] == "code_execution_20250825"
+
+
+def test_claude_skills_middleware_basic_functionality() -> None:
+    """Test ClaudeSkillsMiddleware basic functionality."""
+    middleware = ClaudeSkillsMiddleware(skills=["pptx", "xlsx"])
+
+    mock_chat_anthropic = MagicMock(spec=ChatAnthropic)
+
+    fake_request = ModelRequest(
+        model=mock_chat_anthropic,
+        messages=[HumanMessage("Create a presentation")],
+        system_prompt=None,
+        tool_choice=None,
+        tools=[{"type": "code_execution_20250825", "name": "code_execution"}],
+        response_format=None,
+        state={"messages": [HumanMessage("Create a presentation")]},
+        runtime=cast(Runtime, object()),
+        model_settings={},
+    )
+
+    def mock_handler(req: ModelRequest) -> ModelResponse:
+        return ModelResponse(result=[AIMessage(content="mock response")])
+
+    result = middleware.wrap_model_call(fake_request, mock_handler)
+    assert isinstance(result, ModelResponse)
+
+    # Check that model_settings were properly configured
+    assert "betas" in fake_request.model_settings
+    assert "code-execution-2025-08-25" in fake_request.model_settings["betas"]
+    assert "skills-2025-10-02" in fake_request.model_settings["betas"]
+    assert "files-api-2025-04-14" in fake_request.model_settings["betas"]
+
+    # Check that container with skills was added
+    assert "container" in fake_request.model_settings
+    assert "skills" in fake_request.model_settings["container"]
+    skills = fake_request.model_settings["container"]["skills"]
+    assert len(skills) == 2
+    assert skills[0]["skill_id"] == "pptx"
+    assert skills[1]["skill_id"] == "xlsx"
+
+
+def test_claude_skills_middleware_preserves_existing_betas() -> None:
+    """Test that middleware preserves existing beta headers."""
+    middleware = ClaudeSkillsMiddleware(skills=["pptx"])
+
+    mock_chat_anthropic = MagicMock(spec=ChatAnthropic)
+
+    fake_request = ModelRequest(
+        model=mock_chat_anthropic,
+        messages=[HumanMessage("Create a presentation")],
+        system_prompt=None,
+        tool_choice=None,
+        tools=[{"type": "code_execution_20250825", "name": "code_execution"}],
+        response_format=None,
+        state={"messages": [HumanMessage("Create a presentation")]},
+        runtime=cast(Runtime, object()),
+        model_settings={"betas": ["existing-beta-header"]},
+    )
+
+    def mock_handler(req: ModelRequest) -> ModelResponse:
+        return ModelResponse(result=[AIMessage(content="mock response")])
+
+    middleware.wrap_model_call(fake_request, mock_handler)
+
+    # Check that existing betas are preserved
+    betas = fake_request.model_settings["betas"]
+    assert "existing-beta-header" in betas
+    assert "code-execution-2025-08-25" in betas
+    assert "skills-2025-10-02" in betas
+    assert "files-api-2025-04-14" in betas
+
+
+def test_claude_skills_middleware_unsupported_model() -> None:
+    """Test ClaudeSkillsMiddleware with unsupported model."""
+    fake_request = ModelRequest(
+        model=FakeToolCallingModel(),
+        messages=[HumanMessage("Hello")],
+        system_prompt=None,
+        tool_choice=None,
+        tools=[{"type": "code_execution_20250825", "name": "code_execution"}],
+        response_format=None,
+        state={"messages": [HumanMessage("Hello")]},
+        runtime=cast(Runtime, object()),
+        model_settings={},
+    )
+
+    middleware = ClaudeSkillsMiddleware(
+        skills=["pptx"], unsupported_model_behavior="raise"
+    )
+
+    def mock_handler(req: ModelRequest) -> ModelResponse:
+        return ModelResponse(result=[AIMessage(content="mock response")])
+
+    # Test raise behavior
+    with pytest.raises(
+        ValueError,
+        match="ClaudeSkillsMiddleware only supports Anthropic models",
+    ):
+        middleware.wrap_model_call(fake_request, mock_handler)
+
+    # Test warn behavior
+    middleware = ClaudeSkillsMiddleware(
+        skills=["pptx"], unsupported_model_behavior="warn"
+    )
+
+    with warnings.catch_warnings(record=True) as w:
+        result = middleware.wrap_model_call(fake_request, mock_handler)
+        assert isinstance(result, ModelResponse)
+        assert len(w) == 1
+        assert "ClaudeSkillsMiddleware only supports Anthropic models" in str(
+            w[-1].message
+        )
+
+    # Test ignore behavior
+    middleware = ClaudeSkillsMiddleware(
+        skills=["pptx"], unsupported_model_behavior="ignore"
+    )
+    result = middleware.wrap_model_call(fake_request, mock_handler)
+    assert isinstance(result, ModelResponse)
+
+
+def test_claude_skills_middleware_custom_tool_name() -> None:
+    """Test middleware with custom code execution tool name."""
+    middleware = ClaudeSkillsMiddleware(
+        skills=["pptx"], code_execution_tool_name="custom_code_exec"
+    )
+
+    mock_chat_anthropic = MagicMock(spec=ChatAnthropic)
+
+    # Request with custom tool name
+    fake_request = ModelRequest(
+        model=mock_chat_anthropic,
+        messages=[HumanMessage("Create a presentation")],
+        system_prompt=None,
+        tool_choice=None,
+        tools=[{"type": "custom_exec", "name": "custom_code_exec"}],
+        response_format=None,
+        state={"messages": [HumanMessage("Create a presentation")]},
+        runtime=cast(Runtime, object()),
+        model_settings={},
+    )
+
+    def mock_handler(req: ModelRequest) -> ModelResponse:
+        return ModelResponse(result=[AIMessage(content="mock response")])
+
+    # Should work with custom tool name
+    result = middleware.wrap_model_call(fake_request, mock_handler)
+    assert isinstance(result, ModelResponse)
+
+
+async def test_claude_skills_middleware_async() -> None:
+    """Test ClaudeSkillsMiddleware async path."""
+    middleware = ClaudeSkillsMiddleware(skills=["pptx", "docx"])
+
+    mock_chat_anthropic = MagicMock(spec=ChatAnthropic)
+
+    fake_request = ModelRequest(
+        model=mock_chat_anthropic,
+        messages=[HumanMessage("Create a document")],
+        system_prompt=None,
+        tool_choice=None,
+        tools=[{"type": "code_execution_20250825", "name": "code_execution"}],
+        response_format=None,
+        state={"messages": [HumanMessage("Create a document")]},
+        runtime=cast(Runtime, object()),
+        model_settings={},
+    )
+
+    async def mock_handler(req: ModelRequest) -> ModelResponse:
+        return ModelResponse(result=[AIMessage(content="mock response")])
+
+    result = await middleware.awrap_model_call(fake_request, mock_handler)
+    assert isinstance(result, ModelResponse)
+
+    # Verify skills were configured
+    assert "container" in fake_request.model_settings
+    skills = fake_request.model_settings["container"]["skills"]
+    assert len(skills) == 2
+    assert skills[0]["skill_id"] == "pptx"
+    assert skills[1]["skill_id"] == "docx"
+
+
+async def test_claude_skills_middleware_async_unsupported_model() -> None:
+    """Test ClaudeSkillsMiddleware async path with unsupported model."""
+    fake_request = ModelRequest(
+        model=FakeToolCallingModel(),
+        messages=[HumanMessage("Hello")],
+        system_prompt=None,
+        tool_choice=None,
+        tools=[{"type": "code_execution_20250825", "name": "code_execution"}],
+        response_format=None,
+        state={"messages": [HumanMessage("Hello")]},
+        runtime=cast(Runtime, object()),
+        model_settings={},
+    )
+
+    middleware = ClaudeSkillsMiddleware(
+        skills=["pptx"], unsupported_model_behavior="raise"
+    )
+
+    async def mock_handler(req: ModelRequest) -> ModelResponse:
+        return ModelResponse(result=[AIMessage(content="mock response")])
+
+    # Test raise behavior
+    with pytest.raises(
+        ValueError,
+        match="ClaudeSkillsMiddleware only supports Anthropic models",
+    ):
+        await middleware.awrap_model_call(fake_request, mock_handler)
+
+    # Test warn behavior
+    middleware = ClaudeSkillsMiddleware(
+        skills=["pptx"], unsupported_model_behavior="warn"
+    )
+
+    with warnings.catch_warnings(record=True) as w:
+        result = await middleware.awrap_model_call(fake_request, mock_handler)
+        assert isinstance(result, ModelResponse)
+        assert len(w) == 1
+        assert "ClaudeSkillsMiddleware only supports Anthropic models" in str(
+            w[-1].message
+        )
+
+    # Test ignore behavior
+    middleware = ClaudeSkillsMiddleware(
+        skills=["pptx"], unsupported_model_behavior="ignore"
+    )
+    result = await middleware.awrap_model_call(fake_request, mock_handler)
+    assert isinstance(result, ModelResponse)
+
+
+async def test_claude_skills_middleware_async_code_execution_auto_added() -> None:
+    """Test that async path automatically adds code execution tool."""
+    middleware = ClaudeSkillsMiddleware(skills=["xlsx"])
+
+    mock_chat_anthropic = MagicMock(spec=ChatAnthropic)
+
+    # Request without code execution tool
+    fake_request = ModelRequest(
+        model=mock_chat_anthropic,
+        messages=[HumanMessage("Process spreadsheet")],
+        system_prompt=None,
+        tool_choice=None,
+        tools=[],  # No code execution tool initially
+        response_format=None,
+        state={"messages": [HumanMessage("Process spreadsheet")]},
+        runtime=cast(Runtime, object()),
+        model_settings={},
+    )
+
+    async def mock_handler(req: ModelRequest) -> ModelResponse:
+        return ModelResponse(result=[AIMessage(content="mock response")])
+
+    # Should automatically add code_execution tool
+    result = await middleware.awrap_model_call(fake_request, mock_handler)
+    assert isinstance(result, ModelResponse)
+
+    # Verify code_execution was added to tools
+    assert len(fake_request.tools) == 1
+    tool = fake_request.tools[0]
+    assert isinstance(tool, dict)
+    assert tool["name"] == "code_execution"
+    assert tool["type"] == "code_execution_20250825"
+
+
+def test_claude_skills_middleware_all_pre_built_skills() -> None:
+    """Test middleware with all pre-built Anthropic skills."""
+    middleware = ClaudeSkillsMiddleware(skills=["pptx", "xlsx", "docx", "pdf"])
+
+    mock_chat_anthropic = MagicMock(spec=ChatAnthropic)
+
+    fake_request = ModelRequest(
+        model=mock_chat_anthropic,
+        messages=[HumanMessage("Process documents")],
+        system_prompt=None,
+        tool_choice=None,
+        tools=[{"type": "code_execution_20250825", "name": "code_execution"}],
+        response_format=None,
+        state={"messages": [HumanMessage("Process documents")]},
+        runtime=cast(Runtime, object()),
+        model_settings={},
+    )
+
+    def mock_handler(req: ModelRequest) -> ModelResponse:
+        return ModelResponse(result=[AIMessage(content="mock response")])
+
+    result = middleware.wrap_model_call(fake_request, mock_handler)
+    assert isinstance(result, ModelResponse)
+
+    # Verify all skills are configured
+    skills = fake_request.model_settings["container"]["skills"]
+    assert len(skills) == 4
+    skill_ids = {skill["skill_id"] for skill in skills}
+    assert skill_ids == {"pptx", "xlsx", "docx", "pdf"}
+    # All should be anthropic type with latest version by default
+    for skill in skills:
+        assert skill["type"] == "anthropic"
+        assert skill["version"] == "latest"
+
+
+def test_local_skill_config_initialization() -> None:
+    """Test LocalSkillConfig initialization and validation."""
+    with tempfile.TemporaryDirectory() as temp_dir:
+        skill_dir = Path(temp_dir) / "my-skill"
+        skill_dir.mkdir()
+
+        # Create a valid SKILL.md file
+        skill_md = skill_dir / "SKILL.md"
+        skill_md.write_text(
+            """---
+name: My Custom Skill
+description: A test skill for unit testing
+---
+
+# My Custom Skill
+
+This is a test skill."""
+        )
+
+        # Test successful initialization
+        skill = LocalSkillConfig(path=skill_dir, display_title="Test Skill")
+        assert skill.path == skill_dir
+        assert skill.display_title == "Test Skill"
+        assert skill.type == "custom"
+        assert skill.version == "latest"
+        assert skill.auto_upload is True
+        assert not skill.is_uploaded
+
+        # Test with auto_upload=False
+        skill = LocalSkillConfig(path=skill_dir, auto_upload=False)
+        assert skill.auto_upload is False
+
+
+def test_local_skill_config_missing_path() -> None:
+    """Test LocalSkillConfig with non-existent path."""
+    with pytest.raises(FileNotFoundError, match="Skill path does not exist"):
+        LocalSkillConfig(path="/nonexistent/path")
+
+
+def test_local_skill_config_invalid_path_type() -> None:
+    """Test LocalSkillConfig with invalid path type."""
+    with tempfile.TemporaryDirectory() as temp_dir:
+        # Create a regular file instead of a directory
+        invalid_path = Path(temp_dir) / "invalid.txt"
+        invalid_path.write_text("not a skill")
+
+        with pytest.raises(
+            ValueError,
+            match=r"Skill path must be a directory or \.zip file",
+        ):
+            LocalSkillConfig(path=invalid_path)
+
+
+def test_local_skill_config_missing_skill_md() -> None:
+    """Test LocalSkillConfig with directory missing SKILL.md."""
+    with tempfile.TemporaryDirectory() as temp_dir:
+        skill_dir = Path(temp_dir) / "incomplete-skill"
+        skill_dir.mkdir()
+
+        with pytest.raises(
+            ValueError,
+            match=r"Skill directory must contain a SKILL\.md file",
+        ):
+            LocalSkillConfig(path=skill_dir)
+
+
+def test_local_skill_config_zip_file() -> None:
+    """Test LocalSkillConfig with zip file."""
+    with tempfile.TemporaryDirectory() as temp_dir:
+        # Create a zip file
+        import zipfile
+
+        zip_path = Path(temp_dir) / "skill.zip"
+        with zipfile.ZipFile(zip_path, "w") as zf:
+            zf.writestr(
+                "SKILL.md",
+                """---
+name: Zipped Skill
+description: A skill from a zip file
+---
+
+# Zipped Skill""",
+            )
+
+        # Should initialize successfully
+        skill = LocalSkillConfig(path=zip_path)
+        assert skill.path == zip_path
+        assert skill.type == "custom"
+
+
+def test_local_skill_config_content_hash() -> None:
+    """Test that content hash is computed correctly."""
+    with tempfile.TemporaryDirectory() as temp_dir:
+        skill_dir = Path(temp_dir) / "my-skill"
+        skill_dir.mkdir()
+
+        skill_md = skill_dir / "SKILL.md"
+        skill_md.write_text(
+            """---
+name: Hash Test
+description: Testing hash computation
+---
+
+# Hash Test"""
+        )
+
+        skill = LocalSkillConfig(path=skill_dir)
+        hash1 = skill._compute_content_hash()
+
+        # Hash should be consistent
+        hash2 = skill._compute_content_hash()
+        assert hash1 == hash2
+
+        # Modify content
+        skill_md.write_text(
+            """---
+name: Hash Test Modified
+description: Modified content
+---
+
+# Modified"""
+        )
+
+        # Hash should change
+        hash3 = skill._compute_content_hash()
+        assert hash1 != hash3
+
+
+def test_local_skill_config_create_zip() -> None:
+    """Test creating zip from skill directory."""
+    with tempfile.TemporaryDirectory() as temp_dir:
+        skill_dir = Path(temp_dir) / "my-skill"
+        skill_dir.mkdir()
+
+        # Create multiple files
+        (skill_dir / "SKILL.md").write_text("# Test Skill")
+        (skill_dir / "helper.py").write_text("def helper(): pass")
+
+        # Create subdirectory with file
+        subdir = skill_dir / "scripts"
+        subdir.mkdir()
+        (subdir / "script.py").write_text("print('hello')")
+
+        skill = LocalSkillConfig(path=skill_dir)
+        zip_bytes = skill._create_zip_bytes()
+
+        # Verify it's valid zip
+        import zipfile
+        from io import BytesIO
+
+        with zipfile.ZipFile(BytesIO(zip_bytes), "r") as zf:
+            names = zf.namelist()
+            # Zip should contain top-level folder with all files inside
+            assert "my-skill/SKILL.md" in names
+            assert "my-skill/helper.py" in names
+            assert "my-skill/scripts/script.py" in names
+
+
+def test_local_skill_config_upload() -> None:
+    """Test uploading a local skill."""
+    with tempfile.TemporaryDirectory() as temp_dir:
+        skill_dir = Path(temp_dir) / "my-skill"
+        skill_dir.mkdir()
+        (skill_dir / "SKILL.md").write_text("# Test")
+
+        skill = LocalSkillConfig(path=skill_dir)
+
+        # Mock the Anthropic client
+        mock_client = MagicMock()
+        mock_response = MagicMock()
+        mock_response.id = "skill-123"
+        mock_client.beta.skills.create.return_value = mock_response
+
+        # Upload
+        skill_id = skill.upload_skill(mock_client)
+
+        assert skill_id == "skill-123"
+        assert skill.skill_id == "skill-123"
+        assert skill.is_uploaded
+
+        # Verify upload was called
+        mock_client.beta.skills.create.assert_called_once()
+
+        # Upload again with same content - should not call API again
+        skill_id2 = skill.upload_skill(mock_client)
+        assert skill_id2 == "skill-123"
+        assert mock_client.beta.skills.create.call_count == 1  # Still just 1 call
+
+
+def test_claude_skills_middleware_with_local_skill() -> None:
+    """Test ClaudeSkillsMiddleware with LocalSkillConfig."""
+    with tempfile.TemporaryDirectory() as temp_dir:
+        skill_dir = Path(temp_dir) / "my-skill"
+        skill_dir.mkdir()
+        (skill_dir / "SKILL.md").write_text("# Test Skill")
+
+        # Create middleware with local skill (auto_upload=False)
+        local_skill = LocalSkillConfig(path=skill_dir, auto_upload=False)
+        middleware = ClaudeSkillsMiddleware(skills=["pptx", local_skill])
+
+        # Mock chat model with _client
+        mock_chat_anthropic = MagicMock(spec=ChatAnthropic)
+        mock_client = MagicMock()
+        mock_chat_anthropic._client = mock_client
+
+        # Manually upload the skill first
+        mock_response = MagicMock()
+        mock_response.id = "local-skill-456"
+        mock_client.beta.skills.create.return_value = mock_response
+        local_skill.upload_skill(mock_client)
+
+        fake_request = ModelRequest(
+            model=mock_chat_anthropic,
+            messages=[HumanMessage("Use skills")],
+            system_prompt=None,
+            tool_choice=None,
+            tools=[{"type": "code_execution_20250825", "name": "code_execution"}],
+            response_format=None,
+            state={"messages": [HumanMessage("Use skills")]},
+            runtime=cast(Runtime, object()),
+            model_settings={},
+        )
+
+        def mock_handler(req: ModelRequest) -> ModelResponse:
+            return ModelResponse(result=[AIMessage(content="mock response")])
+
+        result = middleware.wrap_model_call(fake_request, mock_handler)
+        assert isinstance(result, ModelResponse)
+
+        # Verify both skills are configured
+        skills = fake_request.model_settings["container"]["skills"]
+        assert len(skills) == 2
+        skill_ids = {skill["skill_id"] for skill in skills}
+        assert "pptx" in skill_ids
+        assert "local-skill-456" in skill_ids
+
+
+def test_claude_skills_middleware_auto_upload() -> None:
+    """Test that middleware auto-uploads local skills when auto_upload=True."""
+    with tempfile.TemporaryDirectory() as temp_dir:
+        skill_dir = Path(temp_dir) / "auto-skill"
+        skill_dir.mkdir()
+        (skill_dir / "SKILL.md").write_text("# Auto Upload Test")
+
+        # Create middleware with auto_upload=True (default)
+        local_skill = LocalSkillConfig(path=skill_dir)
+        middleware = ClaudeSkillsMiddleware(skills=[local_skill])
+
+        # Mock chat model with _client
+        mock_chat_anthropic = MagicMock(spec=ChatAnthropic)
+        mock_client = MagicMock()
+        mock_chat_anthropic._client = mock_client
+
+        mock_response = MagicMock()
+        mock_response.id = "auto-uploaded-789"
+        mock_client.beta.skills.create.return_value = mock_response
+
+        fake_request = ModelRequest(
+            model=mock_chat_anthropic,
+            messages=[HumanMessage("Test")],
+            system_prompt=None,
+            tool_choice=None,
+            tools=[{"type": "code_execution_20250825", "name": "code_execution"}],
+            response_format=None,
+            state={"messages": [HumanMessage("Test")]},
+            runtime=cast(Runtime, object()),
+            model_settings={},
+        )
+
+        def mock_handler(req: ModelRequest) -> ModelResponse:
+            return ModelResponse(result=[AIMessage(content="mock response")])
+
+        # Should auto-upload during wrap_model_call
+        assert not local_skill.is_uploaded
+        result = middleware.wrap_model_call(fake_request, mock_handler)
+        assert isinstance(result, ModelResponse)
+        assert local_skill.is_uploaded
+        assert local_skill.skill_id == "auto-uploaded-789"
+
+        # Verify upload was called
+        mock_client.beta.skills.create.assert_called_once()
diff --git a/libs/partners/anthropic/uv.lock b/libs/partners/anthropic/uv.lock
index 08c5b6905cfec..da9530b451687 100644
--- a/libs/partners/anthropic/uv.lock
+++ b/libs/partners/anthropic/uv.lock
@@ -10,9 +10,6 @@ resolution-markers = [
     "python_full_version < '3.11' and platform_python_implementation == 'PyPy'",
 ]
 
-[options]
-prerelease-mode = "allow"
-
 [[package]]
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