"""Module contains utility functions for working with messages.

Some examples of what you can do with these functions include:

* Convert messages to strings (serialization)
* Convert messages from dicts to Message objects (deserialization)
* Filter messages from a list of messages based on name, type or id etc.
"""

from __future__ import annotations

import base64
import inspect
import json
import logging
import math
from collections.abc import Callable, Iterable, Sequence
from functools import partial, wraps
from typing import (
    TYPE_CHECKING,
    Annotated,
    Any,
    Concatenate,
    Literal,
    ParamSpec,
    Protocol,
    TypeVar,
    cast,
    overload,
)
from xml.sax.saxutils import escape, quoteattr

from pydantic import Discriminator, Field, Tag

from langchain_core.exceptions import ErrorCode, create_message
from langchain_core.messages.ai import AIMessage, AIMessageChunk
from langchain_core.messages.base import BaseMessage, BaseMessageChunk
from langchain_core.messages.block_translators.openai import (
    convert_to_openai_data_block,
)
from langchain_core.messages.chat import ChatMessage, ChatMessageChunk
from langchain_core.messages.content import (
    is_data_content_block,
)
from langchain_core.messages.function import FunctionMessage, FunctionMessageChunk
from langchain_core.messages.human import HumanMessage, HumanMessageChunk
from langchain_core.messages.modifier import RemoveMessage
from langchain_core.messages.system import SystemMessage, SystemMessageChunk
from langchain_core.messages.tool import ToolCall, ToolMessage, ToolMessageChunk
from langchain_core.utils.pydantic import model_json_schema as get_model_json_schema

if TYPE_CHECKING:
    from langchain_core.language_models import BaseLanguageModel
    from langchain_core.prompt_values import PromptValue
    from langchain_core.runnables.base import Runnable
    from langchain_core.tools import BaseTool

try:
    from langchain_text_splitters import TextSplitter

    _HAS_LANGCHAIN_TEXT_SPLITTERS = True
except ImportError:
    _HAS_LANGCHAIN_TEXT_SPLITTERS = False

logger = logging.getLogger(__name__)


def _get_type(v: Any) -> str:
    """Get the type associated with the object for serialization purposes."""
    if isinstance(v, dict) and "type" in v:
        result = v["type"]
    elif hasattr(v, "type"):
        result = v.type
    else:
        msg = (
            f"Expected either a dictionary with a 'type' key or an object "
            f"with a 'type' attribute. Instead got type {type(v)}."
        )
        raise TypeError(msg)
    if not isinstance(result, str):
        msg = f"Expected 'type' to be a str, got {type(result).__name__}"
        raise TypeError(msg)
    return result


AnyMessage = Annotated[
    Annotated[AIMessage, Tag(tag="ai")]
    | Annotated[HumanMessage, Tag(tag="human")]
    | Annotated[ChatMessage, Tag(tag="chat")]
    | Annotated[SystemMessage, Tag(tag="system")]
    | Annotated[FunctionMessage, Tag(tag="function")]
    | Annotated[ToolMessage, Tag(tag="tool")]
    | Annotated[AIMessageChunk, Tag(tag="AIMessageChunk")]
    | Annotated[HumanMessageChunk, Tag(tag="HumanMessageChunk")]
    | Annotated[ChatMessageChunk, Tag(tag="ChatMessageChunk")]
    | Annotated[SystemMessageChunk, Tag(tag="SystemMessageChunk")]
    | Annotated[FunctionMessageChunk, Tag(tag="FunctionMessageChunk")]
    | Annotated[ToolMessageChunk, Tag(tag="ToolMessageChunk")],
    Field(discriminator=Discriminator(_get_type)),
]
"""A type representing any defined `Message` or `MessageChunk` type."""


def _has_base64_data(block: dict[str, Any]) -> bool:
    """Check if a content block contains base64 encoded data.

    Args:
        block: A content block dictionary.

    Returns:
        Whether the block contains base64 data.
    """
    # Check for explicit base64 field (standard content blocks)
    if block.get("base64"):
        return True

    # Check for data: URL in url field
    url = block.get("url", "")
    if isinstance(url, str) and url.startswith("data:"):
        return True

    # Check for OpenAI-style image_url with data: URL
    image_url = block.get("image_url", {})
    if isinstance(image_url, dict):
        url = image_url.get("url", "")
        if isinstance(url, str) and url.startswith("data:"):
            return True

    return False


_XML_CONTENT_BLOCK_MAX_LEN = 500


def _truncate(text: str, max_len: int = _XML_CONTENT_BLOCK_MAX_LEN) -> str:
    """Truncate text to `max_len` characters, adding ellipsis if truncated."""
    if len(text) <= max_len:
        return text
    return text[:max_len] + "..."


def _format_content_block_xml(block: dict[str, Any]) -> str | None:
    """Format a content block as XML.

    Args:
        block: A LangChain content block.

    Returns:
        XML string representation of the block, or `None` if the block should be
            skipped.

    Note:
        Plain text document content, server tool call arguments, and server tool
        result outputs are truncated to 500 characters.
    """
    block_type = block.get("type", "")

    # Skip blocks with base64 encoded data
    if _has_base64_data(block):
        return None

    # Text blocks
    if block_type == "text":
        text = block.get("text", "")
        return escape(text) if text else None

    # Reasoning blocks
    if block_type == "reasoning":
        reasoning = block.get("reasoning", "")
        if reasoning:
            return f"<reasoning>{escape(reasoning)}</reasoning>"
        return None

    # Image blocks (URL only, base64 already filtered)
    if block_type == "image":
        url = block.get("url")
        file_id = block.get("file_id")
        if url:
            return f"<image url={quoteattr(url)} />"
        if file_id:
            return f"<image file_id={quoteattr(file_id)} />"
        return None

    # OpenAI-style image_url blocks
    if block_type == "image_url":
        image_url = block.get("image_url", {})
        if isinstance(image_url, dict):
            url = image_url.get("url", "")
            if url and not url.startswith("data:"):
                return f"<image url={quoteattr(url)} />"
        return None

    # Audio blocks (URL only)
    if block_type == "audio":
        url = block.get("url")
        file_id = block.get("file_id")
        if url:
            return f"<audio url={quoteattr(url)} />"
        if file_id:
            return f"<audio file_id={quoteattr(file_id)} />"
        return None

    # Video blocks (URL only)
    if block_type == "video":
        url = block.get("url")
        file_id = block.get("file_id")
        if url:
            return f"<video url={quoteattr(url)} />"
        if file_id:
            return f"<video file_id={quoteattr(file_id)} />"
        return None

    # Plain text document blocks
    if block_type == "text-plain":
        text = block.get("text", "")
        return escape(_truncate(text)) if text else None

    # Server tool call blocks (from AI messages)
    if block_type == "server_tool_call":
        tc_id = quoteattr(str(block.get("id") or ""))
        tc_name = quoteattr(str(block.get("name") or ""))
        tc_args_json = json.dumps(block.get("args", {}), ensure_ascii=False)
        tc_args = escape(_truncate(tc_args_json))
        return (
            f"<server_tool_call id={tc_id} name={tc_name}>{tc_args}</server_tool_call>"
        )

    # Server tool result blocks
    if block_type == "server_tool_result":
        tool_call_id = quoteattr(str(block.get("tool_call_id") or ""))
        status = quoteattr(str(block.get("status") or ""))
        output = block.get("output")
        if output:
            output_json = json.dumps(output, ensure_ascii=False)
            output_str = escape(_truncate(output_json))
        else:
            output_str = ""
        return (
            f"<server_tool_result tool_call_id={tool_call_id} status={status}>"
            f"{output_str}</server_tool_result>"
        )

    # Unknown block type - skip silently
    return None


def _get_message_type_str(
    m: BaseMessage,
    human_prefix: str,
    ai_prefix: str,
    system_prefix: str,
    function_prefix: str,
    tool_prefix: str,
) -> str:
    """Get the type string for XML message element.

    Args:
        m: The message to get the type string for.
        human_prefix: The prefix to use for `HumanMessage`.
        ai_prefix: The prefix to use for `AIMessage`.
        system_prefix: The prefix to use for `SystemMessage`.
        function_prefix: The prefix to use for `FunctionMessage`.
        tool_prefix: The prefix to use for `ToolMessage`.

    Returns:
        The type string for the message element.

    Raises:
        ValueError: If an unsupported message type is encountered.
    """
    if isinstance(m, HumanMessage):
        return human_prefix.lower()
    if isinstance(m, AIMessage):
        return ai_prefix.lower()
    if isinstance(m, SystemMessage):
        return system_prefix.lower()
    if isinstance(m, FunctionMessage):
        return function_prefix.lower()
    if isinstance(m, ToolMessage):
        return tool_prefix.lower()
    if isinstance(m, ChatMessage):
        return m.role
    msg = f"Got unsupported message type: {m}"
    raise ValueError(msg)


def get_buffer_string(
    messages: Sequence[BaseMessage],
    human_prefix: str = "Human",
    ai_prefix: str = "AI",
    *,
    system_prefix: str = "System",
    function_prefix: str = "Function",
    tool_prefix: str = "Tool",
    message_separator: str = "\n",
    format: Literal["prefix", "xml"] = "prefix",  # noqa: A002
) -> str:
    r"""Convert a sequence of messages to strings and concatenate them into one string.

    Args:
        messages: Messages to be converted to strings.
        human_prefix: The prefix to prepend to contents of `HumanMessage`s.
        ai_prefix: The prefix to prepend to contents of `AIMessage`.
        system_prefix: The prefix to prepend to contents of `SystemMessage`s.
        function_prefix: The prefix to prepend to contents of `FunctionMessage`s.
        tool_prefix: The prefix to prepend to contents of `ToolMessage`s.
        message_separator: The separator to use between messages.
        format: The output format. `'prefix'` uses `Role: content` format (default).
            For multimodal messages, only string content and `text` blocks are
            included; non-text blocks such as images, audio, and video are omitted.

            `'xml'` uses XML-style `<message type='role'>` format with proper
            character escaping, which is useful when message content may
            contain role-like prefixes that could cause ambiguity.

            Use `'xml'` when you need a structured representation of supported
            multimodal content blocks.

    Returns:
        A single string concatenation of all input messages.

    Raises:
        ValueError: If an unsupported message type is encountered.

    !!! warning

        If a message is an `AIMessage` and contains both tool calls under `tool_calls`
        and a function call under `additional_kwargs["function_call"]`, only the tool
        calls will be appended to the string representation.

    !!! note "XML format"

        When using `format='xml'`:

        - All messages use uniform `<message type="role">content</message>` format.
        - The `type` attribute uses `human_prefix` (lowercased) for `HumanMessage`,
            `ai_prefix` (lowercased) for `AIMessage`, `system_prefix` (lowercased)
            for `SystemMessage`, `function_prefix` (lowercased) for `FunctionMessage`,
            `tool_prefix` (lowercased) for `ToolMessage`, and the original role
            (unchanged) for `ChatMessage`.
        - Message content is escaped using `xml.sax.saxutils.escape()`.
        - Attribute values are escaped using `xml.sax.saxutils.quoteattr()`.
        - AI messages with tool calls use nested structure with `<content>` and
            `<tool_call>` elements.
        - For multi-modal content (list of content blocks), supported block types
            are: `text`, `reasoning`, `image` (URL/file_id only), `image_url`
            (OpenAI-style, URL only), `audio` (URL/file_id only), `video` (URL/file_id
            only), `text-plain`, `server_tool_call`, and `server_tool_result`.
        - Content blocks with base64-encoded data are skipped (including blocks
            with `base64` field or `data:` URLs).
        - Unknown block types are skipped.
        - Plain text document content (`text-plain`), server tool call arguments,
            and server tool result outputs are truncated to 500 characters.

    Example:
        Default prefix format:

        ```python
        from langchain_core.messages import AIMessage, HumanMessage, get_buffer_string

        messages = [
            HumanMessage(content="Hi, how are you?"),
            AIMessage(content="Good, how are you?"),
        ]
        get_buffer_string(messages)
        # -> "Human: Hi, how are you?\nAI: Good, how are you?"
        ```

        XML format (useful when content contains role-like prefixes):

        ```python
        messages = [
            HumanMessage(content="Example: Human: some text"),
            AIMessage(content="I see the example."),
        ]
        get_buffer_string(messages, format="xml")
        # -> '<message type="human">Example: Human: some text</message>\\n'
        # -> '<message type="ai">I see the example.</message>'
        ```

        XML format with special characters (automatically escaped):

        ```python
        messages = [
            HumanMessage(content="Is 5 < 10 & 10 > 5?"),
        ]
        get_buffer_string(messages, format="xml")
        # -> '<message type="human">Is 5 &lt; 10 &amp; 10 &gt; 5?</message>'
        ```

        XML format with tool calls:

        ```python
        messages = [
            AIMessage(
                content="I'll search for that.",
                tool_calls=[
                    {"id": "call_123", "name": "search", "args": {"query": "weather"}}
                ],
            ),
        ]
        get_buffer_string(messages, format="xml")
        # -> '<message type="ai">\\n'
        # -> '  <content>I\\'ll search for that.</content>\\n'
        # -> '  <tool_call id="call_123" name="search">'
        # -> '{"query": "weather"}</tool_call>\\n'
        # -> '</message>'
        ```
    """
    if format not in {"prefix", "xml"}:
        msg = (
            f"Unrecognized format={format!r}. Supported formats are 'prefix' and 'xml'."
        )
        raise ValueError(msg)

    string_messages = []
    for m in messages:
        if isinstance(m, HumanMessage):
            role = human_prefix
        elif isinstance(m, AIMessage):
            role = ai_prefix
        elif isinstance(m, SystemMessage):
            role = system_prefix
        elif isinstance(m, FunctionMessage):
            role = function_prefix
        elif isinstance(m, ToolMessage):
            role = tool_prefix
        elif isinstance(m, ChatMessage):
            role = m.role
        else:
            msg = f"Got unsupported message type: {m}"
            raise ValueError(msg)  # noqa: TRY004

        if format == "xml":
            msg_type = _get_message_type_str(
                m, human_prefix, ai_prefix, system_prefix, function_prefix, tool_prefix
            )

            # Format content blocks
            if isinstance(m.content, str):
                content_parts = [escape(m.content)] if m.content else []
            else:
                # List of content blocks
                content_parts = []
                for block in m.content:
                    if isinstance(block, str):
                        if block:
                            content_parts.append(escape(block))
                    else:
                        formatted = _format_content_block_xml(block)
                        if formatted:
                            content_parts.append(formatted)

            # Check if this is an AIMessage with tool calls
            has_tool_calls = isinstance(m, AIMessage) and m.tool_calls
            has_function_call = (
                isinstance(m, AIMessage)
                and not m.tool_calls
                and "function_call" in m.additional_kwargs
            )

            if has_tool_calls or has_function_call:
                # Use nested structure for AI messages with tool calls
                # Type narrowing: at this point m is AIMessage (verified above)
                ai_msg = cast("AIMessage", m)
                parts = [f"<message type={quoteattr(msg_type)}>"]
                if content_parts:
                    parts.append(f"  <content>{' '.join(content_parts)}</content>")

                if has_tool_calls:
                    for tc in ai_msg.tool_calls:
                        tc_id = quoteattr(str(tc.get("id") or ""))
                        tc_name = quoteattr(str(tc.get("name") or ""))
                        tc_args = escape(
                            json.dumps(tc.get("args", {}), ensure_ascii=False)
                        )
                        parts.append(
                            f"  <tool_call id={tc_id} name={tc_name}>"
                            f"{tc_args}</tool_call>"
                        )
                elif has_function_call:
                    fc = ai_msg.additional_kwargs["function_call"]
                    fc_name = quoteattr(str(fc.get("name") or ""))
                    fc_args = escape(str(fc.get("arguments") or "{}"))
                    parts.append(
                        f"  <function_call name={fc_name}>{fc_args}</function_call>"
                    )

                parts.append("</message>")
                message = "\n".join(parts)
            else:
                # Simple structure for messages without tool calls
                joined_content = " ".join(content_parts)
                message = (
                    f"<message type={quoteattr(msg_type)}>{joined_content}</message>"
                )
        else:  # format == "prefix"
            content = m.text
            message = f"{role}: {content}"
            tool_info = ""
            if isinstance(m, AIMessage):
                if m.tool_calls:
                    tool_info = str(m.tool_calls)
                elif "function_call" in m.additional_kwargs:
                    # Legacy behavior assumes only one function call per message
                    tool_info = str(m.additional_kwargs["function_call"])
            if tool_info:
                message += tool_info  # Preserve original behavior

        string_messages.append(message)

    return message_separator.join(string_messages)


def _message_from_dict(message: dict[str, Any]) -> BaseMessage:
    type_ = message["type"]
    if type_ == "human":
        return HumanMessage(**message["data"])
    if type_ == "ai":
        return AIMessage(**message["data"])
    if type_ == "system":
        return SystemMessage(**message["data"])
    if type_ == "chat":
        return ChatMessage(**message["data"])
    if type_ == "function":
        return FunctionMessage(**message["data"])
    if type_ == "tool":
        return ToolMessage(**message["data"])
    if type_ == "remove":
        return RemoveMessage(**message["data"])
    if type_ == "AIMessageChunk":
        return AIMessageChunk(**message["data"])
    if type_ == "HumanMessageChunk":
        return HumanMessageChunk(**message["data"])
    if type_ == "FunctionMessageChunk":
        return FunctionMessageChunk(**message["data"])
    if type_ == "ToolMessageChunk":
        return ToolMessageChunk(**message["data"])
    if type_ == "SystemMessageChunk":
        return SystemMessageChunk(**message["data"])
    if type_ == "ChatMessageChunk":
        return ChatMessageChunk(**message["data"])
    msg = f"Got unexpected message type: {type_}"
    raise ValueError(msg)


def messages_from_dict(messages: Sequence[dict[str, Any]]) -> list[BaseMessage]:
    """Convert a sequence of messages from dicts to `Message` objects.

    Args:
        messages: Sequence of messages (as dicts) to convert.

    Returns:
        list of messages (BaseMessages).

    """
    return [_message_from_dict(m) for m in messages]


def message_chunk_to_message(chunk: BaseMessage) -> BaseMessage:
    """Convert a message chunk to a `Message`.

    Args:
        chunk: Message chunk to convert.

    Returns:
        Message.
    """
    if not isinstance(chunk, BaseMessageChunk):
        return chunk
    # chunk classes always have the equivalent non-chunk class as their first parent
    ignore_keys = ["type"]
    if isinstance(chunk, AIMessageChunk):
        ignore_keys.extend(["tool_call_chunks", "chunk_position"])
    return cast(
        "BaseMessage",
        chunk.__class__.__mro__[1](
            **{k: v for k, v in chunk.__dict__.items() if k not in ignore_keys}
        ),
    )


MessageLikeRepresentation = (
    BaseMessage
    | list[str]
    | tuple[str, str | list[str | dict[str, Any]]]
    | str
    | dict[str, Any]
)
"""A type representing the various ways a message can be represented."""


def _create_message_from_message_type(
    message_type: str,
    content: str | list[str | dict[str, Any]],
    name: str | None = None,
    tool_call_id: str | None = None,
    tool_calls: list[dict[str, Any]] | None = None,
    id: str | None = None,
    **additional_kwargs: Any,
) -> BaseMessage:
    """Create a message from a `Message` type and content string.

    Args:
        message_type: the type of the message (e.g., `'human'`, `'ai'`, etc.).
        content: the content string.
        name: the name of the message.
        tool_call_id: the tool call id.
        tool_calls: the tool calls.
        id: the id of the message.
        additional_kwargs: additional keyword arguments.

    Returns:
        a message of the appropriate type.

    Raises:
        ValueError: if the message type is not one of `'human'`, `'user'`, `'ai'`,
            `'assistant'`, `'function'`, `'tool'`, `'system'`, or
            `'developer'`.
    """
    kwargs: dict[str, Any] = {}
    if name is not None:
        kwargs["name"] = name
    if tool_call_id is not None:
        kwargs["tool_call_id"] = tool_call_id
    if additional_kwargs:
        if response_metadata := additional_kwargs.pop("response_metadata", None):
            kwargs["response_metadata"] = response_metadata
        kwargs["additional_kwargs"] = additional_kwargs
        additional_kwargs.update(additional_kwargs.pop("additional_kwargs", {}))
    if id is not None:
        kwargs["id"] = id
    if tool_calls is not None:
        kwargs["tool_calls"] = []
        for tool_call in tool_calls:
            # Convert OpenAI-format tool call to LangChain format.
            if "function" in tool_call:
                args = tool_call["function"]["arguments"]
                if isinstance(args, str):
                    args = json.loads(args, strict=False)
                kwargs["tool_calls"].append(
                    {
                        "name": tool_call["function"]["name"],
                        "args": args,
                        "id": tool_call["id"],
                        "type": "tool_call",
                    }
                )
            else:
                kwargs["tool_calls"].append(tool_call)
    if message_type in {"human", "user"}:
        if example := kwargs.get("additional_kwargs", {}).pop("example", False):
            kwargs["example"] = example
        message: BaseMessage = HumanMessage(content=content, **kwargs)
    elif message_type in {"ai", "assistant"}:
        if example := kwargs.get("additional_kwargs", {}).pop("example", False):
            kwargs["example"] = example
        message = AIMessage(content=content, **kwargs)
    elif message_type in {"system", "developer"}:
        if message_type == "developer":
            kwargs["additional_kwargs"] = kwargs.get("additional_kwargs") or {}
            kwargs["additional_kwargs"]["__openai_role__"] = "developer"
        message = SystemMessage(content=content, **kwargs)
    elif message_type == "function":
        message = FunctionMessage(content=content, **kwargs)
    elif message_type == "tool":
        artifact = kwargs.get("additional_kwargs", {}).pop("artifact", None)
        status = kwargs.get("additional_kwargs", {}).pop("status", None)
        if status is not None:
            kwargs["status"] = status
        message = ToolMessage(content=content, artifact=artifact, **kwargs)
    elif message_type == "remove":
        message = RemoveMessage(**kwargs)
    else:
        msg = (
            f"Unexpected message type: '{message_type}'. Use one of 'human',"
            f" 'user', 'ai', 'assistant', 'function', 'tool', 'system', or 'developer'."
        )
        msg = create_message(message=msg, error_code=ErrorCode.MESSAGE_COERCION_FAILURE)
        raise ValueError(msg)
    return message


# Map of class names emitted in the `Serializable` constructor-envelope
# (`{"lc": 1, "type": "constructor", "id": [..., "<ClassName>"],
# "kwargs": {...}}`) to the message-type strings
# `_create_message_from_message_type` accepts. Read by
# `_convert_to_message`'s dict branch when unpacking that wire shape.
# Kept as a hardcoded allowlist of strings rather than a class registry
# lookup so dispatch never resolves to a class chosen by the caller.
_LC_CONSTRUCTOR_NAME_TO_TYPE: dict[str, str] = {
    "HumanMessage": "human",
    "HumanMessageChunk": "human",
    "AIMessage": "ai",
    "AIMessageChunk": "ai",
    "SystemMessage": "system",
    "SystemMessageChunk": "system",
    "FunctionMessage": "function",
    "FunctionMessageChunk": "function",
    "ToolMessage": "tool",
    "ToolMessageChunk": "tool",
    "RemoveMessage": "remove",
}


def _convert_to_message(message: MessageLikeRepresentation) -> BaseMessage:
    """Instantiate a `Message` from a variety of message formats.

    The message format can be one of the following:

    - `BaseMessagePromptTemplate`
    - `BaseMessage`
    - 2-tuple of (role string, template); e.g., (`'human'`, `'{user_input}'`)
    - dict: a message dict with role and content keys
    - dict: the `Serializable` constructor-envelope wire shape
        `{"lc": 1, "type": "constructor", "id": [..., "<ClassName>"],
        "kwargs": {...}}` — unpacked structurally and routed through the
        standard dict-with-type dispatch.
    - string: shorthand for (`'human'`, template); e.g., `'{user_input}'`

    Args:
        message: a representation of a message in one of the supported formats.

    Returns:
        An instance of a message or a message template.

    Raises:
        NotImplementedError: if the message type is not supported.
        ValueError: if the message dict does not contain the required keys.

    """
    if isinstance(message, BaseMessage):
        message_ = message
    elif isinstance(message, Sequence):
        if isinstance(message, str):
            message_ = _create_message_from_message_type("human", message)
        else:
            try:
                message_type_str, template = message
            except ValueError as e:
                msg = "Message as a sequence must be (role string, template)"
                raise NotImplementedError(msg) from e
            message_ = _create_message_from_message_type(message_type_str, template)
    elif isinstance(message, dict):
        # `Serializable` constructor-envelope wire shape. Detect structurally, map
        # the class name to a known message-type string via a hardcoded
        # allowlist, and recurse with the canonical
        # `{"type": ..., **kwargs}` shape — no `load()`, no dynamic
        # class instantiation.
        if (
            message.get("lc") == 1
            and message.get("type") == "constructor"
            and isinstance(message.get("id"), list)
            and message["id"]
            and isinstance(message.get("kwargs"), dict)
        ):
            mapped = _LC_CONSTRUCTOR_NAME_TO_TYPE.get(message["id"][-1])
            if mapped is not None:
                return _convert_to_message({"type": mapped, **message["kwargs"]})

        msg_kwargs = message.copy()
        try:
            try:
                msg_type = msg_kwargs.pop("role")
            except KeyError:
                msg_type = msg_kwargs.pop("type")
            # None msg content is not allowed
            msg_content = msg_kwargs.pop("content") or ""
        except KeyError as e:
            msg = f"Message dict must contain 'role' and 'content' keys, got {message}"
            msg = create_message(
                message=msg, error_code=ErrorCode.MESSAGE_COERCION_FAILURE
            )
            raise ValueError(msg) from e
        message_ = _create_message_from_message_type(
            msg_type, msg_content, **msg_kwargs
        )
    else:
        msg = f"Unsupported message type: {type(message)}"  # type: ignore[unreachable]
        msg = create_message(message=msg, error_code=ErrorCode.MESSAGE_COERCION_FAILURE)
        raise NotImplementedError(msg)

    return message_


def convert_to_messages(
    messages: Iterable[MessageLikeRepresentation] | PromptValue,
) -> list[BaseMessage]:
    """Convert a sequence of messages to a list of messages.

    Args:
        messages: Sequence of messages to convert.

    Returns:
        list of messages (BaseMessages).

    """
    # Import here to avoid circular imports
    from langchain_core.prompt_values import PromptValue  # noqa: PLC0415

    if isinstance(messages, PromptValue):
        return messages.to_messages()
    return [_convert_to_message(m) for m in messages]


_P = ParamSpec("_P")
_R_co = TypeVar("_R_co", covariant=True)


class _RunnableSupportCallable(Protocol[_P, _R_co]):
    @overload
    def __call__(
        self,
        messages: None = None,
        *args: _P.args,
        **kwargs: _P.kwargs,
    ) -> Runnable[Sequence[MessageLikeRepresentation], _R_co]: ...

    @overload
    def __call__(
        self,
        messages: Sequence[MessageLikeRepresentation] | PromptValue,
        *args: _P.args,
        **kwargs: _P.kwargs,
    ) -> _R_co: ...

    def __call__(
        self,
        messages: Sequence[MessageLikeRepresentation] | PromptValue | None = None,
        *args: _P.args,
        **kwargs: _P.kwargs,
    ) -> _R_co | Runnable[Sequence[MessageLikeRepresentation], _R_co]: ...


def _runnable_support(
    func: Callable[
        Concatenate[Sequence[MessageLikeRepresentation] | PromptValue, _P], _R_co
    ],
) -> _RunnableSupportCallable[_P, _R_co]:
    @wraps(func)
    def wrapped(
        messages: Sequence[MessageLikeRepresentation] | PromptValue | None = None,
        *args: _P.args,
        **kwargs: _P.kwargs,
    ) -> _R_co | Runnable[Sequence[MessageLikeRepresentation], _R_co]:
        # Import locally to prevent circular import.
        from langchain_core.runnables.base import RunnableLambda  # noqa: PLC0415

        if messages is not None:
            return func(messages, *args, **kwargs)
        return RunnableLambda(partial(func, **kwargs), name=func.__name__)

    return cast("_RunnableSupportCallable[_P, _R_co]", wrapped)


@_runnable_support
def filter_messages(
    messages: Iterable[MessageLikeRepresentation] | PromptValue,
    *,
    include_names: Sequence[str] | None = None,
    exclude_names: Sequence[str] | None = None,
    include_types: Sequence[str | type[BaseMessage]] | None = None,
    exclude_types: Sequence[str | type[BaseMessage]] | None = None,
    include_ids: Sequence[str] | None = None,
    exclude_ids: Sequence[str] | None = None,
    exclude_tool_calls: Sequence[str] | bool | None = None,
) -> list[BaseMessage]:
    """Filter messages based on `name`, `type` or `id`.

    Args:
        messages: Sequence Message-like objects to filter.
        include_names: Message names to include.
        exclude_names: Messages names to exclude.
        include_types: Message types to include. Can be specified as string names
            (e.g. `'system'`, `'human'`, `'ai'`, ...) or as `BaseMessage`
            classes (e.g. `SystemMessage`, `HumanMessage`, `AIMessage`, ...).

        exclude_types: Message types to exclude. Can be specified as string names
            (e.g. `'system'`, `'human'`, `'ai'`, ...) or as `BaseMessage`
            classes (e.g. `SystemMessage`, `HumanMessage`, `AIMessage`, ...).

        include_ids: Message IDs to include.
        exclude_ids: Message IDs to exclude.
        exclude_tool_calls: Tool call IDs to exclude.
            Can be one of the following:
            - `True`: All `AIMessage` objects with tool calls and all `ToolMessage`
                objects will be excluded.
            - a sequence of tool call IDs to exclude:
                - `ToolMessage` objects with the corresponding tool call ID will be
                    excluded.
                - The `tool_calls` in the AIMessage will be updated to exclude
                    matching tool calls. If all `tool_calls` are filtered from an
                    AIMessage, the whole message is excluded.

    Returns:
        A list of Messages that meets at least one of the `incl_*` conditions and none
        of the `excl_*` conditions. If not `incl_*` conditions are specified then
        anything that is not explicitly excluded will be included.

    Raises:
        ValueError: If two incompatible arguments are provided.

    Example:
        ```python
        from langchain_core.messages import (
            filter_messages,
            AIMessage,
            HumanMessage,
            SystemMessage,
        )

        messages = [
            SystemMessage("you're a good assistant."),
            HumanMessage("what's your name", id="foo", name="example_user"),
            AIMessage("steve-o", id="bar", name="example_assistant"),
            HumanMessage(
                "what's your favorite color",
                id="baz",
            ),
            AIMessage(
                "silicon blue",
                id="blah",
            ),
        ]

        filter_messages(
            messages,
            include_names=("example_user", "example_assistant"),
            include_types=("system",),
            exclude_ids=("bar",),
        )
        ```

        ```python
        [
            SystemMessage("you're a good assistant."),
            HumanMessage("what's your name", id="foo", name="example_user"),
        ]
        ```
    """
    messages = convert_to_messages(messages)
    filtered: list[BaseMessage] = []
    for msg in messages:
        if (
            (exclude_names and msg.name in exclude_names)
            or (exclude_types and _is_message_type(msg, exclude_types))
            or (exclude_ids and msg.id in exclude_ids)
        ):
            continue

        if exclude_tool_calls is True and (
            (isinstance(msg, AIMessage) and msg.tool_calls)
            or isinstance(msg, ToolMessage)
        ):
            continue

        new_msg = msg
        if isinstance(exclude_tool_calls, (list, tuple, set)):
            if isinstance(msg, AIMessage) and msg.tool_calls:
                tool_calls = [
                    tool_call
                    for tool_call in msg.tool_calls
                    if tool_call["id"] not in exclude_tool_calls
                ]
                if not tool_calls:
                    continue

                content = msg.content
                # handle Anthropic content blocks
                if isinstance(msg.content, list):
                    content = [
                        content_block
                        for content_block in msg.content
                        if (
                            not isinstance(content_block, dict)
                            or content_block.get("type") != "tool_use"
                            or content_block.get("id") not in exclude_tool_calls
                        )
                    ]

                new_msg = msg.model_copy(
                    update={"tool_calls": tool_calls, "content": content}
                )
            elif (
                isinstance(msg, ToolMessage) and msg.tool_call_id in exclude_tool_calls
            ):
                continue

        # default to inclusion when no inclusion criteria given.
        if (
            not (include_types or include_ids or include_names)
            or (include_names and new_msg.name in include_names)
            or (include_types and _is_message_type(new_msg, include_types))
            or (include_ids and new_msg.id in include_ids)
        ):
            filtered.append(new_msg)

    return filtered


@_runnable_support
def merge_message_runs(
    messages: Iterable[MessageLikeRepresentation] | PromptValue,
    *,
    chunk_separator: str = "\n",
) -> list[BaseMessage]:
    r"""Merge consecutive Messages of the same type.

    !!! note
        `ToolMessage` objects are not merged, as each has a distinct tool call id that
        can't be merged.

    Args:
        messages: Sequence Message-like objects to merge.
        chunk_separator: Specify the string to be inserted between message chunks.

    Returns:
        list of BaseMessages with consecutive runs of message types merged into single
        messages. By default, if two messages being merged both have string contents,
        the merged content is a concatenation of the two strings with a new-line
        separator.
        The separator inserted between message chunks can be controlled by specifying
        any string with `chunk_separator`. If at least one of the messages has a list
        of content blocks, the merged content is a list of content blocks.

    Example:
        ```python
        from langchain_core.messages import (
            merge_message_runs,
            AIMessage,
            HumanMessage,
            SystemMessage,
            ToolCall,
        )

        messages = [
            SystemMessage("you're a good assistant."),
            HumanMessage(
                "what's your favorite color",
                id="foo",
            ),
            HumanMessage(
                "wait your favorite food",
                id="bar",
            ),
            AIMessage(
                "my favorite colo",
                tool_calls=[
                    ToolCall(
                        name="blah_tool", args={"x": 2}, id="123", type="tool_call"
                    )
                ],
                id="baz",
            ),
            AIMessage(
                [{"type": "text", "text": "my favorite dish is lasagna"}],
                tool_calls=[
                    ToolCall(
                        name="blah_tool",
                        args={"x": -10},
                        id="456",
                        type="tool_call",
                    )
                ],
                id="blur",
            ),
        ]

        merge_message_runs(messages)
        ```

        ```python
        [
            SystemMessage("you're a good assistant."),
            HumanMessage(
                "what's your favorite color\\n"
                "wait your favorite food", id="foo",
            ),
            AIMessage(
                [
                    "my favorite colo",
                    {"type": "text", "text": "my favorite dish is lasagna"}
                ],
                tool_calls=[
                    ToolCall({
                        "name": "blah_tool",
                        "args": {"x": 2},
                        "id": "123",
                        "type": "tool_call"
                    }),
                    ToolCall({
                        "name": "blah_tool",
                        "args": {"x": -10},
                        "id": "456",
                        "type": "tool_call"
                    })
                ]
                id="baz"
            ),
        ]

        ```
    """
    if not messages:
        return []
    messages = convert_to_messages(messages)
    merged: list[BaseMessage] = []
    for msg in messages:
        last = merged.pop() if merged else None
        if not last:
            merged.append(msg)
        elif isinstance(msg, ToolMessage) or not isinstance(msg, last.__class__):
            merged.extend([last, msg])
        else:
            last_chunk = _msg_to_chunk(last)
            curr_chunk = _msg_to_chunk(msg)
            if curr_chunk.response_metadata:
                curr_chunk.response_metadata.clear()
            if (
                isinstance(last_chunk.content, str)
                and isinstance(curr_chunk.content, str)
                and last_chunk.content
                and curr_chunk.content
            ):
                last_chunk.content += chunk_separator
            merged.append(_chunk_to_msg(last_chunk + curr_chunk))
    return merged


# TODO: Update so validation errors (for token_counter, for example) are raised on
# init not at runtime.
@_runnable_support
def trim_messages(
    messages: Iterable[MessageLikeRepresentation] | PromptValue,
    *,
    max_tokens: int,
    token_counter: Callable[[list[BaseMessage]], int]
    | Callable[[BaseMessage], int]
    | BaseLanguageModel[Any]
    | Literal["approximate"],
    strategy: Literal["first", "last"] = "last",
    allow_partial: bool = False,
    end_on: str | type[BaseMessage] | Sequence[str | type[BaseMessage]] | None = None,
    start_on: str | type[BaseMessage] | Sequence[str | type[BaseMessage]] | None = None,
    include_system: bool = False,
    text_splitter: Callable[[str], list[str]] | TextSplitter | None = None,
) -> list[BaseMessage]:
    r"""Trim messages to be below a token count.

    `trim_messages` can be used to reduce the size of a chat history to a specified
    token or message count.

    In either case, if passing the trimmed chat history back into a chat model
    directly, the resulting chat history should usually satisfy the following
    properties:

    1. The resulting chat history should be valid. Most chat models expect that chat
        history starts with either (1) a `HumanMessage` or (2) a `SystemMessage`
        followed by a `HumanMessage`. To achieve this, set `start_on='human'`.
        In addition, generally a `ToolMessage` can only appear after an `AIMessage`
        that involved a tool call.
    2. It includes recent messages and drops old messages in the chat history.
        To achieve this set the `strategy='last'`.
    3. Usually, the new chat history should include the `SystemMessage` if it
        was present in the original chat history since the `SystemMessage` includes
        special instructions to the chat model. The `SystemMessage` is almost always
        the first message in the history if present. To achieve this set the
        `include_system=True`.

    !!! note
        The examples below show how to configure `trim_messages` to achieve a behavior
        consistent with the above properties.

    Args:
        messages: Sequence of Message-like objects to trim.
        max_tokens: Max token count of trimmed messages.
        token_counter: Function or llm for counting tokens in a `BaseMessage` or a
            list of `BaseMessage`.

            If a `BaseLanguageModel` is passed in then
            `BaseLanguageModel.get_num_tokens_from_messages()` will be used. Set to
            `len` to count the number of **messages** in the chat history.

            You can also use string shortcuts for convenience:

            - `'approximate'`: Uses `count_tokens_approximately` for fast, approximate
                token counts.

            !!! note

                `count_tokens_approximately` (or the shortcut `'approximate'`) is
                recommended for using `trim_messages` on the hot path, where exact token
                counting is not necessary.

        strategy: Strategy for trimming.

            - `'first'`: Keep the first `<= n_count` tokens of the messages.
            - `'last'`: Keep the last `<= n_count` tokens of the messages.
        allow_partial: Whether to split a message if only part of the message can be
            included.

            If `strategy='last'` then the last partial contents of a message are
            included. If `strategy='first'` then the first partial contents of a
            message are included.
        end_on: The message type to end on.

            If specified then every message after the last occurrence of this type is
            ignored. If `strategy='last'` then this is done before we attempt to get the
            last `max_tokens`. If `strategy='first'` then this is done after we get the
            first `max_tokens`. Can be specified as string names (e.g. `'system'`,
            `'human'`, `'ai'`, ...) or as `BaseMessage` classes (e.g. `SystemMessage`,
            `HumanMessage`, `AIMessage`, ...). Can be a single type or a list of types.

        start_on: The message type to start on.

            Should only be specified if `strategy='last'`. If specified then every
            message before the first occurrence of this type is ignored. This is done
            after we trim the initial messages to the last `max_tokens`. Does not apply
            to a `SystemMessage` at index 0 if `include_system=True`. Can be specified
            as string names (e.g. `'system'`, `'human'`, `'ai'`, ...) or as
            `BaseMessage` classes (e.g. `SystemMessage`, `HumanMessage`, `AIMessage`,
            ...). Can be a single type or a list of types.

        include_system: Whether to keep the `SystemMessage` if there is one at index
            `0`.

            Should only be specified if `strategy="last"`.
        text_splitter: Function or `langchain_text_splitters.TextSplitter` for
            splitting the string contents of a message.

            Only used if `allow_partial=True`. If `strategy='last'` then the last split
            tokens from a partial message will be included. if `strategy='first'` then
            the first split tokens from a partial message will be included. Token
            splitter assumes that separators are kept, so that split contents can be
            directly concatenated to recreate the original text. Defaults to splitting
            on newlines.

    Returns:
        List of trimmed `BaseMessage`.

    Raises:
        ValueError: if two incompatible arguments are specified or an unrecognized
            `strategy` is specified.

    Example:
        Trim chat history based on token count, keeping the `SystemMessage` if
        present, and ensuring that the chat history starts with a `HumanMessage` (or a
        `SystemMessage` followed by a `HumanMessage`).

        ```python
        from langchain_core.messages import (
            AIMessage,
            HumanMessage,
            BaseMessage,
            SystemMessage,
            trim_messages,
        )

        messages = [
            SystemMessage("you're a good assistant, you always respond with a joke."),
            HumanMessage("i wonder why it's called langchain"),
            AIMessage(
                'Well, I guess they thought "WordRope" and "SentenceString" just '
                "didn't have the same ring to it!"
            ),
            HumanMessage("and who is harrison chasing anyways"),
            AIMessage(
                "Hmmm let me think.\n\nWhy, he's probably chasing after the last "
                "cup of coffee in the office!"
            ),
            HumanMessage("what do you call a speechless parrot"),
        ]


        trim_messages(
            messages,
            max_tokens=45,
            strategy="last",
            token_counter=ChatOpenAI(model="openai:gpt-5.5"),
            # Most chat models expect that chat history starts with either:
            # (1) a HumanMessage or
            # (2) a SystemMessage followed by a HumanMessage
            start_on="human",
            # Usually, we want to keep the SystemMessage
            # if it's present in the original history.
            # The SystemMessage has special instructions for the model.
            include_system=True,
            allow_partial=False,
        )
        ```

        ```python
        [
            SystemMessage(
                content="you're a good assistant, you always respond with a joke."
            ),
            HumanMessage(content="what do you call a speechless parrot"),
        ]
        ```

        Trim chat history using approximate token counting with `'approximate'`:

        ```python
        trim_messages(
            messages,
            max_tokens=45,
            strategy="last",
            # Using the "approximate" shortcut for fast token counting
            token_counter="approximate",
            start_on="human",
            include_system=True,
        )

        # This is equivalent to using `count_tokens_approximately` directly
        from langchain_core.messages.utils import count_tokens_approximately

        trim_messages(
            messages,
            max_tokens=45,
            strategy="last",
            token_counter=count_tokens_approximately,
            start_on="human",
            include_system=True,
        )
        ```

        Trim chat history based on the message count, keeping the `SystemMessage` if
        present, and ensuring that the chat history starts with a HumanMessage (
        or a `SystemMessage` followed by a `HumanMessage`).

            trim_messages(
                messages,
                # When `len` is passed in as the token counter function,
                # max_tokens will count the number of messages in the chat history.
                max_tokens=4,
                strategy="last",
                # Passing in `len` as a token counter function will
                # count the number of messages in the chat history.
                token_counter=len,
                # Most chat models expect that chat history starts with either:
                # (1) a HumanMessage or
                # (2) a SystemMessage followed by a HumanMessage
                start_on="human",
                # Usually, we want to keep the SystemMessage
                # if it's present in the original history.
                # The SystemMessage has special instructions for the model.
                include_system=True,
                allow_partial=False,
            )

        ```python
        [
            SystemMessage(
                content="you're a good assistant, you always respond with a joke."
            ),
            HumanMessage(content="and who is harrison chasing anyways"),
            AIMessage(
                content="Hmmm let me think.\n\nWhy, he's probably chasing after "
                "the last cup of coffee in the office!"
            ),
            HumanMessage(content="what do you call a speechless parrot"),
        ]
        ```
        Trim chat history using a custom token counter function that counts the
        number of tokens in each message.

        ```python
        messages = [
            SystemMessage("This is a 4 token text. The full message is 10 tokens."),
            HumanMessage(
                "This is a 4 token text. The full message is 10 tokens.", id="first"
            ),
            AIMessage(
                [
                    {"type": "text", "text": "This is the FIRST 4 token block."},
                    {"type": "text", "text": "This is the SECOND 4 token block."},
                ],
                id="second",
            ),
            HumanMessage(
                "This is a 4 token text. The full message is 10 tokens.", id="third"
            ),
            AIMessage(
                "This is a 4 token text. The full message is 10 tokens.",
                id="fourth",
            ),
        ]


        def dummy_token_counter(messages: list[BaseMessage]) -> int:
            # treat each message like it adds 3 default tokens at the beginning
            # of the message and at the end of the message. 3 + 4 + 3 = 10 tokens
            # per message.

            default_content_len = 4
            default_msg_prefix_len = 3
            default_msg_suffix_len = 3

            count = 0
            for msg in messages:
                if isinstance(msg.content, str):
                    count += (
                        default_msg_prefix_len
                        + default_content_len
                        + default_msg_suffix_len
                    )
                if isinstance(msg.content, list):
                    count += (
                        default_msg_prefix_len
                        + len(msg.content) * default_content_len
                        + default_msg_suffix_len
                    )
            return count
        ```

        First 30 tokens, allowing partial messages:
        ```python
        trim_messages(
            messages,
            max_tokens=30,
            token_counter=dummy_token_counter,
            strategy="first",
            allow_partial=True,
        )
        ```

        ```python
        [
            SystemMessage("This is a 4 token text. The full message is 10 tokens."),
            HumanMessage(
                "This is a 4 token text. The full message is 10 tokens.",
                id="first",
            ),
            AIMessage(
                [{"type": "text", "text": "This is the FIRST 4 token block."}],
                id="second",
            ),
        ]
        ```
    """
    # Validate arguments
    if start_on and strategy == "first":
        msg = "start_on parameter is only valid with strategy='last'"
        raise ValueError(msg)
    if include_system and strategy == "first":
        msg = "include_system parameter is only valid with strategy='last'"
        raise ValueError(msg)

    messages = convert_to_messages(messages)

    # Handle string shortcuts for token counter
    if isinstance(token_counter, str):
        if token_counter in _TOKEN_COUNTER_SHORTCUTS:
            actual_token_counter = _TOKEN_COUNTER_SHORTCUTS[token_counter]
        else:
            available_shortcuts = ", ".join(
                f"'{key}'" for key in _TOKEN_COUNTER_SHORTCUTS
            )
            msg = (
                f"Invalid token_counter shortcut '{token_counter}'. "
                f"Available shortcuts: {available_shortcuts}."
            )
            raise ValueError(msg)
    else:
        # Type narrowing: at this point token_counter is not a str
        actual_token_counter = token_counter  # type: ignore[assignment]

    if hasattr(actual_token_counter, "get_num_tokens_from_messages"):
        list_token_counter = actual_token_counter.get_num_tokens_from_messages
    elif callable(actual_token_counter):
        if (
            next(
                iter(inspect.signature(actual_token_counter).parameters.values())
            ).annotation
            is BaseMessage
        ):

            def list_token_counter(messages: Sequence[BaseMessage]) -> int:
                return sum(actual_token_counter(msg) for msg in messages)  # type: ignore[arg-type, misc]

        else:
            list_token_counter = actual_token_counter
    else:
        msg = (  # type: ignore[unreachable]
            f"'token_counter' expected to be a model that implements "
            f"'get_num_tokens_from_messages()' or a function. Received object of type "
            f"{type(actual_token_counter)}."
        )
        raise ValueError(msg)

    text_splitter_fn: Callable[[str], list[str]]
    if _HAS_LANGCHAIN_TEXT_SPLITTERS and isinstance(text_splitter, TextSplitter):
        text_splitter_fn = text_splitter.split_text
    elif text_splitter:
        text_splitter_fn = cast("Callable[[str], list[str]]", text_splitter)
    else:
        text_splitter_fn = _default_text_splitter

    if strategy == "first":
        return _first_max_tokens(
            messages,
            max_tokens=max_tokens,
            token_counter=list_token_counter,
            text_splitter=text_splitter_fn,
            partial_strategy="first" if allow_partial else None,
            end_on=end_on,
        )
    if strategy == "last":
        return _last_max_tokens(
            messages,
            max_tokens=max_tokens,
            token_counter=list_token_counter,
            allow_partial=allow_partial,
            include_system=include_system,
            start_on=start_on,
            end_on=end_on,
            text_splitter=text_splitter_fn,
        )
    msg = f"Unrecognized {strategy=}. Supported strategies are 'last' and 'first'."  # type: ignore[unreachable]
    raise ValueError(msg)


_SingleMessage = BaseMessage | str | dict[str, Any]
_T = TypeVar("_T", bound=_SingleMessage)
# A sequence of _SingleMessage that is NOT a bare str
_MultipleMessages = Sequence[_T]


@overload
def convert_to_openai_messages(
    messages: _SingleMessage,
    *,
    text_format: Literal["string", "block"] = "string",
    include_id: bool = False,
    pass_through_unknown_blocks: bool = True,
) -> dict[str, Any]: ...


@overload
def convert_to_openai_messages(
    messages: _MultipleMessages[Any],
    *,
    text_format: Literal["string", "block"] = "string",
    include_id: bool = False,
    pass_through_unknown_blocks: bool = True,
) -> list[dict[str, Any]]: ...


def convert_to_openai_messages(
    messages: MessageLikeRepresentation | Sequence[MessageLikeRepresentation],
    *,
    text_format: Literal["string", "block"] = "string",
    include_id: bool = False,
    pass_through_unknown_blocks: bool = True,
) -> dict[str, Any] | list[dict[str, Any]]:
    """Convert LangChain messages into OpenAI message dicts.

    Args:
        messages: Message-like object or iterable of objects whose contents are
            in OpenAI, Anthropic, Bedrock Converse, or VertexAI formats.
        text_format: How to format string or text block contents:
            - `'string'`:
                If a message has a string content, this is left as a string. If
                a message has content blocks that are all of type `'text'`, these
                are joined with a newline to make a single string. If a message has
                content blocks and at least one isn't of type `'text'`, then
                all blocks are left as dicts.
            - `'block'`:
                If a message has a string content, this is turned into a list
                with a single content block of type `'text'`. If a message has
                content blocks these are left as is.
        include_id: Whether to include message IDs in the openai messages, if they
            are present in the source messages.
        pass_through_unknown_blocks: Whether to include content blocks with unknown
            formats in the output. If `False`, an error is raised if an unknown
            content block is encountered.

    Raises:
        ValueError: if an unrecognized `text_format` is specified, or if a message
            content block is missing expected keys.

    Returns:
        The return type depends on the input type:

        - dict:
            If a single message-like object is passed in, a single OpenAI message
            dict is returned.
        - list[dict]:
            If a sequence of message-like objects are passed in, a list of OpenAI
            message dicts is returned.

    Example:
        ```python
        from langchain_core.messages import (
            convert_to_openai_messages,
            AIMessage,
            SystemMessage,
            ToolMessage,
        )

        messages = [
            SystemMessage([{"type": "text", "text": "foo"}]),
            {
                "role": "user",
                "content": [
                    {"type": "text", "text": "what's in this"},
                    {
                        "type": "image_url",
                        "image_url": {"url": "data:image/png;base64,'/9j/4AAQSk'"},
                    },
                ],
            },
            AIMessage(
                "",
                tool_calls=[
                    {
                        "name": "analyze",
                        "args": {"baz": "buz"},
                        "id": "1",
                        "type": "tool_call",
                    }
                ],
            ),
            ToolMessage("foobar", tool_call_id="1", name="bar"),
            {"role": "assistant", "content": "that's nice"},
        ]
        oai_messages = convert_to_openai_messages(messages)
        # -> [
        #   {'role': 'system', 'content': 'foo'},
        #   {'role': 'user', 'content': [{'type': 'text', 'text': 'what's in this'}, {'type': 'image_url', 'image_url': {'url': "data:image/png;base64,'/9j/4AAQSk'"}}]},
        #   {'role': 'assistant', 'tool_calls': [{'type': 'function', 'id': '1','function': {'name': 'analyze', 'arguments': '{"baz": "buz"}'}}], 'content': ''},
        #   {'role': 'tool', 'name': 'bar', 'content': 'foobar'},
        #   {'role': 'assistant', 'content': 'that's nice'}
        # ]
        ```

    !!! version-added "Added in `langchain-core` 0.3.11"

    """  # noqa: E501
    if text_format not in {"string", "block"}:
        err = f"Unrecognized {text_format=}, expected one of 'string' or 'block'."
        raise ValueError(err)

    oai_messages: list[dict[str, Any]] = []

    messages_: Sequence[MessageLikeRepresentation]
    if is_single := isinstance(messages, (BaseMessage, dict, str)):
        messages_ = [messages]
    else:
        messages_ = cast("Sequence[MessageLikeRepresentation]", messages)

    for i, message in enumerate(convert_to_messages(messages_)):
        oai_msg: dict[str, Any] = {"role": _get_message_openai_role(message)}
        tool_messages: list[dict[str, Any]] = []
        content: str | list[dict[str, Any]]

        if message.name:
            oai_msg["name"] = message.name
        if isinstance(message, AIMessage) and message.tool_calls:
            oai_msg["tool_calls"] = _convert_to_openai_tool_calls(message.tool_calls)
        if message.additional_kwargs.get("refusal"):
            oai_msg["refusal"] = message.additional_kwargs["refusal"]
        if isinstance(message, ToolMessage):
            oai_msg["tool_call_id"] = message.tool_call_id
        if include_id and message.id:
            oai_msg["id"] = message.id

        if not message.content:
            content = "" if text_format == "string" else []
        elif isinstance(message.content, str):
            if text_format == "string":
                content = message.content
            else:
                content = [{"type": "text", "text": message.content}]
        elif text_format == "string" and all(
            isinstance(block, str) or block.get("type") == "text"
            for block in message.content
        ):
            content = "\n".join(
                block if isinstance(block, str) else block["text"]
                for block in message.content
            )
        else:
            content = []
            for j, block in enumerate(message.content):
                # OpenAI format
                if isinstance(block, str):
                    content.append({"type": "text", "text": block})
                elif block.get("type") == "text":
                    if missing := [k for k in ("text",) if k not in block]:
                        err = (
                            f"Unrecognized content block at "
                            f"messages[{i}].content[{j}] has 'type': 'text' "
                            f"but is missing expected key(s) "
                            f"{missing}. Full content block:\n\n{block}"
                        )
                        raise ValueError(err)
                    content.append({"type": block["type"], "text": block["text"]})
                elif block.get("type") == "image_url":
                    if missing := [k for k in ("image_url",) if k not in block]:
                        err = (
                            f"Unrecognized content block at "
                            f"messages[{i}].content[{j}] has 'type': 'image_url' "
                            f"but is missing expected key(s) "
                            f"{missing}. Full content block:\n\n{block}"
                        )
                        raise ValueError(err)
                    content.append(
                        {
                            "type": "image_url",
                            "image_url": block["image_url"],
                        }
                    )
                # Standard multi-modal content block
                elif is_data_content_block(block):
                    formatted_block = convert_to_openai_data_block(block)
                    if (
                        formatted_block.get("type") == "file"
                        and "file" in formatted_block
                        and "filename" not in formatted_block["file"]
                    ):
                        logger.info("Generating a fallback filename.")
                        formatted_block["file"]["filename"] = "LC_AUTOGENERATED"
                    content.append(formatted_block)
                # Anthropic and Bedrock converse format
                elif (block.get("type") == "image") or "image" in block:
                    # Anthropic
                    if source := block.get("source"):
                        if missing := [
                            k for k in ("media_type", "type", "data") if k not in source
                        ]:
                            err = (
                                f"Unrecognized content block at "
                                f"messages[{i}].content[{j}] has 'type': 'image' "
                                f"but 'source' is missing expected key(s) "
                                f"{missing}. Full content block:\n\n{block}"
                            )
                            raise ValueError(err)
                        content.append(
                            {
                                "type": "image_url",
                                "image_url": {
                                    "url": (
                                        f"data:{source['media_type']};"
                                        f"{source['type']},{source['data']}"
                                    )
                                },
                            }
                        )
                    # Bedrock converse
                    elif image := block.get("image"):
                        if missing := [
                            k for k in ("source", "format") if k not in image
                        ]:
                            err = (
                                f"Unrecognized content block at "
                                f"messages[{i}].content[{j}] has key 'image', "
                                f"but 'image' is missing expected key(s) "
                                f"{missing}. Full content block:\n\n{block}"
                            )
                            raise ValueError(err)
                        b64_image = _bytes_to_b64_str(image["source"]["bytes"])
                        content.append(
                            {
                                "type": "image_url",
                                "image_url": {
                                    "url": (
                                        f"data:image/{image['format']};base64,{b64_image}"
                                    )
                                },
                            }
                        )
                    else:
                        err = (
                            f"Unrecognized content block at "
                            f"messages[{i}].content[{j}] has 'type': 'image' "
                            f"but does not have a 'source' or 'image' key. Full "
                            f"content block:\n\n{block}"
                        )
                        raise ValueError(err)
                # OpenAI file format
                elif (
                    block.get("type") == "file"
                    and isinstance(block.get("file"), dict)
                    and isinstance(block.get("file", {}).get("file_data"), str)
                ):
                    if block.get("file", {}).get("filename") is None:
                        logger.info("Generating a fallback filename.")
                        block["file"]["filename"] = "LC_AUTOGENERATED"
                    content.append(block)
                # OpenAI audio format
                elif (
                    block.get("type") == "input_audio"
                    and isinstance(block.get("input_audio"), dict)
                    and isinstance(block.get("input_audio", {}).get("data"), str)
                    and isinstance(block.get("input_audio", {}).get("format"), str)
                ):
                    content.append(block)
                elif block.get("type") == "tool_use":
                    if missing := [
                        k for k in ("id", "name", "input") if k not in block
                    ]:
                        err = (
                            f"Unrecognized content block at "
                            f"messages[{i}].content[{j}] has 'type': "
                            f"'tool_use', but is missing expected key(s) "
                            f"{missing}. Full content block:\n\n{block}"
                        )
                        raise ValueError(err)
                    if not any(
                        tool_call["id"] == block["id"]
                        for tool_call in cast("AIMessage", message).tool_calls
                    ):
                        oai_msg["tool_calls"] = oai_msg.get("tool_calls", [])
                        oai_msg["tool_calls"].append(
                            {
                                "type": "function",
                                "id": block["id"],
                                "function": {
                                    "name": block["name"],
                                    "arguments": json.dumps(
                                        block["input"], ensure_ascii=False
                                    ),
                                },
                            }
                        )
                elif block.get("type") == "function_call":  # OpenAI Responses
                    if not any(
                        tool_call["id"] == block.get("call_id")
                        for tool_call in cast("AIMessage", message).tool_calls
                    ):
                        if missing := [
                            k
                            for k in ("call_id", "name", "arguments")
                            if k not in block
                        ]:
                            err = (
                                f"Unrecognized content block at "
                                f"messages[{i}].content[{j}] has 'type': "
                                f"'tool_use', but is missing expected key(s) "
                                f"{missing}. Full content block:\n\n{block}"
                            )
                            raise ValueError(err)
                        oai_msg["tool_calls"] = oai_msg.get("tool_calls", [])
                        oai_msg["tool_calls"].append(
                            {
                                "type": "function",
                                "id": block.get("call_id"),
                                "function": {
                                    "name": block.get("name"),
                                    "arguments": block.get("arguments"),
                                },
                            }
                        )
                    if pass_through_unknown_blocks:
                        content.append(block)
                elif block.get("type") == "tool_result":
                    if missing := [
                        k for k in ("content", "tool_use_id") if k not in block
                    ]:
                        msg = (
                            f"Unrecognized content block at "
                            f"messages[{i}].content[{j}] has 'type': "
                            f"'tool_result', but is missing expected key(s) "
                            f"{missing}. Full content block:\n\n{block}"
                        )
                        raise ValueError(msg)
                    tool_message = ToolMessage(
                        block["content"],
                        tool_call_id=block["tool_use_id"],
                        status="error" if block.get("is_error") else "success",
                    )
                    # Recurse to make sure tool message contents are OpenAI format.
                    tool_messages.extend(
                        convert_to_openai_messages(
                            [tool_message], text_format=text_format
                        )
                    )
                elif (block.get("type") == "json") or "json" in block:
                    if "json" not in block:
                        msg = (
                            f"Unrecognized content block at "
                            f"messages[{i}].content[{j}] has 'type': 'json' "
                            f"but does not have a 'json' key. Full "
                            f"content block:\n\n{block}"
                        )
                        raise ValueError(msg)
                    content.append(
                        {
                            "type": "text",
                            "text": json.dumps(block["json"]),
                        }
                    )
                elif (block.get("type") == "guard_content") or "guard_content" in block:
                    if (
                        "guard_content" not in block
                        or "text" not in block["guard_content"]
                    ):
                        msg = (
                            f"Unrecognized content block at "
                            f"messages[{i}].content[{j}] has 'type': "
                            f"'guard_content' but does not have a "
                            f"messages[{i}].content[{j}]['guard_content']['text'] "
                            f"key. Full content block:\n\n{block}"
                        )
                        raise ValueError(msg)
                    text = block["guard_content"]["text"]
                    if isinstance(text, dict):
                        text = text["text"]
                    content.append({"type": "text", "text": text})
                # VertexAI format
                elif block.get("type") == "media":
                    if missing := [k for k in ("mime_type", "data") if k not in block]:
                        err = (
                            f"Unrecognized content block at "
                            f"messages[{i}].content[{j}] has 'type': "
                            f"'media' but does not have key(s) {missing}. Full "
                            f"content block:\n\n{block}"
                        )
                        raise ValueError(err)
                    if "image" not in block["mime_type"]:
                        err = (
                            f"OpenAI messages can only support text and image data."
                            f" Received content block with media of type:"
                            f" {block['mime_type']}"
                        )
                        raise ValueError(err)
                    b64_image = _bytes_to_b64_str(block["data"])
                    content.append(
                        {
                            "type": "image_url",
                            "image_url": {
                                "url": (f"data:{block['mime_type']};base64,{b64_image}")
                            },
                        }
                    )
                elif (
                    block.get("type") in {"thinking", "reasoning"}
                    or pass_through_unknown_blocks
                ):
                    content.append(block)
                else:
                    err = (
                        f"Unrecognized content block at "
                        f"messages[{i}].content[{j}] does not match OpenAI, "
                        f"Anthropic, Bedrock Converse, or VertexAI format. Full "
                        f"content block:\n\n{block}"
                    )
                    raise ValueError(err)
            if text_format == "string" and not any(
                block["type"] != "text" for block in content
            ):
                content = "\n".join(block["text"] for block in content)
        oai_msg["content"] = content
        if message.content and not oai_msg["content"] and tool_messages:
            oai_messages.extend(tool_messages)
        else:
            oai_messages.extend([oai_msg, *tool_messages])

    if is_single:
        return oai_messages[0]
    return oai_messages


def _first_max_tokens(
    messages: Sequence[BaseMessage],
    *,
    max_tokens: int,
    token_counter: Callable[[list[BaseMessage]], int],
    text_splitter: Callable[[str], list[str]],
    partial_strategy: Literal["first", "last"] | None = None,
    end_on: str | type[BaseMessage] | Sequence[str | type[BaseMessage]] | None = None,
) -> list[BaseMessage]:
    messages = list(messages)
    if not messages:
        return messages

    # Check if all messages already fit within token limit
    if token_counter(messages) <= max_tokens:
        # When all messages fit, only apply end_on filtering if needed
        if end_on:
            for _ in range(len(messages)):
                if not _is_message_type(messages[-1], end_on):
                    messages.pop()
                else:
                    break
        return messages

    # Use binary search to find the maximum number of messages within token limit
    left, right = 0, len(messages)
    max_iterations = len(messages).bit_length()
    for _ in range(max_iterations):
        if left >= right:
            break
        mid = (left + right + 1) // 2
        if token_counter(messages[:mid]) <= max_tokens:
            left = mid
            idx = mid
        else:
            right = mid - 1

    # idx now contains the maximum number of complete messages we can include
    idx = left

    if partial_strategy and idx < len(messages):
        included_partial = False
        copied = False
        if isinstance(messages[idx].content, list):
            excluded = messages[idx].model_copy(deep=True)
            copied = True
            num_block = len(excluded.content)
            if partial_strategy == "last":
                excluded.content = list(reversed(excluded.content))
            for _ in range(1, num_block):
                excluded.content = excluded.content[:-1]
                if token_counter([*messages[:idx], excluded]) <= max_tokens:
                    messages = [*messages[:idx], excluded]
                    idx += 1
                    included_partial = True
                    break
            if included_partial and partial_strategy == "last":
                excluded.content = list(reversed(excluded.content))
        if not included_partial:
            if not copied:
                excluded = messages[idx].model_copy(deep=True)
                copied = True

            # Extract text content efficiently
            text = None
            if isinstance(excluded.content, str):
                text = excluded.content
            elif isinstance(excluded.content, list) and excluded.content:
                for block in excluded.content:
                    if isinstance(block, str):
                        text = block
                        break
                    if isinstance(block, dict) and block.get("type") == "text":
                        text = block.get("text")
                        break

            if text:
                if not copied:
                    excluded = excluded.model_copy(deep=True)

                split_texts = text_splitter(text)
                base_message_count = token_counter(messages[:idx])
                if partial_strategy == "last":
                    split_texts = list(reversed(split_texts))

                # Binary search for the maximum number of splits we can include
                left, right = 0, len(split_texts)
                max_iterations = len(split_texts).bit_length()
                for _ in range(max_iterations):
                    if left >= right:
                        break
                    mid = (left + right + 1) // 2
                    excluded.content = "".join(split_texts[:mid])
                    if base_message_count + token_counter([excluded]) <= max_tokens:
                        left = mid
                    else:
                        right = mid - 1

                if left > 0:
                    content_splits = split_texts[:left]
                    if partial_strategy == "last":
                        content_splits = list(reversed(content_splits))
                    excluded.content = "".join(content_splits)
                    messages = [*messages[:idx], excluded]
                    idx += 1

    if end_on:
        for _ in range(idx):
            if idx > 0 and not _is_message_type(messages[idx - 1], end_on):
                idx -= 1
            else:
                break

    return messages[:idx]


def _last_max_tokens(
    messages: Sequence[BaseMessage],
    *,
    max_tokens: int,
    token_counter: Callable[[list[BaseMessage]], int],
    text_splitter: Callable[[str], list[str]],
    allow_partial: bool = False,
    include_system: bool = False,
    start_on: str | type[BaseMessage] | Sequence[str | type[BaseMessage]] | None = None,
    end_on: str | type[BaseMessage] | Sequence[str | type[BaseMessage]] | None = None,
) -> list[BaseMessage]:
    messages = list(messages)
    if len(messages) == 0:
        return []

    # Filter out messages after end_on type
    if end_on:
        for _ in range(len(messages)):
            if not _is_message_type(messages[-1], end_on):
                messages.pop()
            else:
                break

    # Handle system message preservation
    system_message = None
    if include_system and len(messages) > 0 and isinstance(messages[0], SystemMessage):
        system_message = messages[0]
        messages = messages[1:]

    # Reverse messages to use _first_max_tokens with reversed logic
    reversed_messages = messages[::-1]

    # Calculate remaining tokens after accounting for system message if present
    remaining_tokens = max_tokens
    if system_message:
        system_tokens = token_counter([system_message])
        remaining_tokens = max(0, max_tokens - system_tokens)

    reversed_result = _first_max_tokens(
        reversed_messages,
        max_tokens=remaining_tokens,
        token_counter=token_counter,
        text_splitter=text_splitter,
        partial_strategy="last" if allow_partial else None,
        end_on=start_on,
    )

    # Re-reverse the messages and add back the system message if needed
    result = reversed_result[::-1]
    if system_message:
        result = [system_message, *result]

    return result


_MSG_CHUNK_MAP: dict[type[BaseMessage], type[BaseMessageChunk]] = {
    HumanMessage: HumanMessageChunk,
    AIMessage: AIMessageChunk,
    SystemMessage: SystemMessageChunk,
    ToolMessage: ToolMessageChunk,
    FunctionMessage: FunctionMessageChunk,
    ChatMessage: ChatMessageChunk,
}
_CHUNK_MSG_MAP = {v: k for k, v in _MSG_CHUNK_MAP.items()}


def _msg_to_chunk(message: BaseMessage) -> BaseMessageChunk:
    if message.__class__ in _MSG_CHUNK_MAP:
        return _MSG_CHUNK_MAP[message.__class__](**message.model_dump(exclude={"type"}))

    for msg_cls, chunk_cls in _MSG_CHUNK_MAP.items():
        if isinstance(message, msg_cls):
            return chunk_cls(**message.model_dump(exclude={"type"}))

    msg = (
        f"Unrecognized message class {message.__class__}. Supported classes are "
        f"{list(_MSG_CHUNK_MAP.keys())}"
    )
    msg = create_message(message=msg, error_code=ErrorCode.MESSAGE_COERCION_FAILURE)
    raise ValueError(msg)


def _chunk_to_msg(chunk: BaseMessageChunk) -> BaseMessage:
    if chunk.__class__ in _CHUNK_MSG_MAP:
        return _CHUNK_MSG_MAP[chunk.__class__](
            **chunk.model_dump(exclude={"type", "tool_call_chunks", "chunk_position"})
        )
    for chunk_cls, msg_cls in _CHUNK_MSG_MAP.items():
        if isinstance(chunk, chunk_cls):
            return msg_cls(
                **chunk.model_dump(
                    exclude={"type", "tool_call_chunks", "chunk_position"}
                )
            )

    msg = (
        f"Unrecognized message chunk class {chunk.__class__}. Supported classes are "
        f"{list(_CHUNK_MSG_MAP.keys())}"
    )
    msg = create_message(message=msg, error_code=ErrorCode.MESSAGE_COERCION_FAILURE)
    raise ValueError(msg)


def _default_text_splitter(text: str) -> list[str]:
    splits = text.split("\n")
    return [s + "\n" for s in splits[:-1]] + splits[-1:]


def _is_message_type(
    message: BaseMessage,
    type_: str | type[BaseMessage] | Sequence[str | type[BaseMessage]],
) -> bool:
    types = [type_] if isinstance(type_, (str, type)) else type_
    types_str = [t for t in types if isinstance(t, str)]
    types_types = tuple(t for t in types if isinstance(t, type))

    return message.type in types_str or isinstance(message, types_types)


def _bytes_to_b64_str(bytes_: bytes) -> str:
    return base64.b64encode(bytes_).decode("utf-8")


def _get_message_openai_role(message: BaseMessage) -> str:
    if isinstance(message, AIMessage):
        return "assistant"
    if isinstance(message, HumanMessage):
        return "user"
    if isinstance(message, ToolMessage):
        return "tool"
    if isinstance(message, SystemMessage):
        role = message.additional_kwargs.get("__openai_role__", "system")
        if not isinstance(role, str):
            msg = f"Expected '__openai_role__' to be a str, got {type(role).__name__}"
            raise TypeError(msg)
        return role
    if isinstance(message, FunctionMessage):
        return "function"
    if isinstance(message, ChatMessage):
        return message.role
    msg = f"Unknown BaseMessage type {message.__class__}."
    raise ValueError(msg)


def _convert_to_openai_tool_calls(tool_calls: list[ToolCall]) -> list[dict[str, Any]]:
    return [
        {
            "type": "function",
            "id": tool_call["id"],
            "function": {
                "name": tool_call["name"],
                "arguments": json.dumps(tool_call["args"], ensure_ascii=False),
            },
        }
        for tool_call in tool_calls
    ]


def count_tokens_approximately(
    messages: Iterable[MessageLikeRepresentation],
    *,
    chars_per_token: float = 4.0,
    extra_tokens_per_message: float = 3.0,
    count_name: bool = True,
    tokens_per_image: int = 85,
    use_usage_metadata_scaling: bool = False,
    tools: list[BaseTool | dict[str, Any]] | None = None,
) -> int:
    """Approximate the total number of tokens in messages.

    The token count includes stringified message content, role, and (optionally) name.

    - For AI messages, the token count also includes stringified tool calls.
    - For tool messages, the token count also includes the tool call ID.
    - For multimodal messages with images, applies a fixed token penalty per image
        instead of counting base64-encoded characters.
    - If tools are provided, the token count also includes stringified tool schemas.

    Args:
        messages: List of messages to count tokens for.
        chars_per_token: Number of characters per token to use for the approximation.
            One token corresponds to ~4 chars for common English text.
            You can also specify `float` values for more fine-grained control.
            [See more here](https://platform.openai.com/tokenizer).
        extra_tokens_per_message: Number of extra tokens to add per message, e.g.
            special tokens, including beginning/end of message.
            You can also specify `float` values for more fine-grained control.
            [See more here](https://github.com/openai/openai-cookbook/blob/main/examples/How_to_count_tokens_with_tiktoken.ipynb).
        count_name: Whether to include message names in the count.
        tokens_per_image: Fixed token cost per image (default: 85, aligned with
            OpenAI's low-resolution image token cost).
        use_usage_metadata_scaling: If True, and all AI messages have consistent
            `response_metadata['model_provider']`, scale the approximate token count
            using the **most recent** AI message that has
            `usage_metadata['total_tokens']`. The scaling factor is:
            `AI_total_tokens / approx_tokens_up_to_that_AI_message`
        tools: List of tools to include in the token count. Each tool can be a
            `BaseTool` instance, a dict representing a tool schema, or a plain
            callable. `BaseTool` instances and callables are converted to
            OpenAI tool format before counting.

    Returns:
        Approximate number of tokens in the messages (and tools, if provided).

    Note:
        This is a simple approximation that may not match the exact token count used by
        specific models. For accurate counts, use model-specific tokenizers.

        For multimodal messages containing images, a fixed token penalty is applied
        per image instead of counting base64-encoded characters, which provides a
        more realistic approximation.

    !!! version-added "Added in `langchain-core` 0.3.46"
    """
    converted_messages = convert_to_messages(messages)

    token_count = 0.0

    ai_model_provider: str | None = None
    invalid_model_provider = False
    last_ai_total_tokens: int | None = None
    approx_at_last_ai: float | None = None

    # Count tokens for tools if provided
    if tools:
        tools_chars = 0
        for tool in tools:
            if isinstance(tool, dict):
                tool_dict = tool
            else:
                # tool_call_schema is memoized per instance
                schema = tool.tool_call_schema
                if isinstance(schema, dict):
                    parameters = dict(schema)
                else:
                    parameters = dict(get_model_json_schema(schema))
                # Drop the schema's own `title`/`description` to avoid double-counting:
                # they're duplicated at the top level.
                parameters.pop("title", None)
                parameters.pop("description", None)
                tool_dict = {
                    "name": tool.name,
                    "description": tool.description,
                    "parameters": parameters,
                }
            tools_chars += len(json.dumps(tool_dict))
        token_count += math.ceil(tools_chars / chars_per_token)

    for message in converted_messages:
        message_chars = 0

        if isinstance(message.content, str):
            message_chars += len(message.content)
        # Handle multimodal content (list of content blocks)
        elif isinstance(message.content, list):
            for block in message.content:
                if isinstance(block, str):
                    # String block
                    message_chars += len(block)
                elif isinstance(block, dict):
                    block_type = block.get("type", "")

                    # Apply fixed penalty for image blocks
                    if block_type in {"image", "image_url"}:
                        token_count += tokens_per_image
                    # Count text blocks normally
                    elif block_type == "text":
                        text = block.get("text", "")
                        message_chars += len(text)
                    # Conservative estimate for unknown block types
                    else:
                        message_chars += len(repr(block))
                else:
                    # Fallback for unexpected block types
                    message_chars += len(repr(block))  # type: ignore[unreachable]
        else:
            # Fallback for other content types
            content = repr(message.content)  # type: ignore[unreachable]
            message_chars += len(content)

        if (
            isinstance(message, AIMessage)
            # exclude Anthropic format as tool calls are already included in the content
            and not isinstance(message.content, list)
            and message.tool_calls
        ):
            tool_calls_content = repr(message.tool_calls)
            message_chars += len(tool_calls_content)

        if isinstance(message, ToolMessage):
            message_chars += len(message.tool_call_id)

        role = _get_message_openai_role(message)
        message_chars += len(role)

        if message.name and count_name:
            message_chars += len(message.name)

        # NOTE: we're rounding up per message to ensure that
        # individual message token counts add up to the total count
        # for a list of messages
        token_count += math.ceil(message_chars / chars_per_token)

        # add extra tokens per message
        token_count += extra_tokens_per_message

        if use_usage_metadata_scaling and isinstance(message, AIMessage):
            model_provider = message.response_metadata.get("model_provider")
            if ai_model_provider is None:
                ai_model_provider = model_provider
            elif model_provider != ai_model_provider:
                invalid_model_provider = True

            if message.usage_metadata and isinstance(
                (total_tokens := message.usage_metadata.get("total_tokens")), int
            ):
                last_ai_total_tokens = total_tokens
                approx_at_last_ai = token_count

    if (
        use_usage_metadata_scaling
        and len(converted_messages) > 1
        and not invalid_model_provider
        and ai_model_provider is not None
        and last_ai_total_tokens is not None
        and approx_at_last_ai
        and approx_at_last_ai > 0
    ):
        scale_factor = last_ai_total_tokens / approx_at_last_ai
        token_count *= min(1.25, max(1.0, scale_factor))

    # round up once more time in case extra_tokens_per_message is a float
    return math.ceil(token_count)


# Mapping from string shortcuts to token counter functions
def _approximate_token_counter(messages: Sequence[BaseMessage]) -> int:
    """Wrapper for `count_tokens_approximately` that matches expected signature."""
    return count_tokens_approximately(messages)


_TOKEN_COUNTER_SHORTCUTS = {
    "approximate": _approximate_token_counter,
}
