gmail_tools.py

"""
Google Gmail MCP Tools

This module provides MCP tools for interacting with the Gmail API.
"""

import logging
import asyncio
import base64
import ssl
import mimetypes
from pathlib import Path
from html.parser import HTMLParser
from typing import Optional, List, Dict, Literal, Any

from email.mime.text import MIMEText
from email.mime.multipart import MIMEMultipart
from email.mime.base import MIMEBase
from email import encoders
from email.utils import formataddr

from fastapi import Body
from pydantic import Field

from auth.service_decorator import require_google_service
from core.utils import handle_http_errors
from core.server import server
from fastmcp.tools.tool import ToolResult

from auth.scopes import (
    GMAIL_SEND_SCOPE,
    GMAIL_COMPOSE_SCOPE,
    GMAIL_MODIFY_SCOPE,
    GMAIL_LABELS_SCOPE,
)
from core.structured_output import create_tool_result
from gmail.gmail_models import (
    GmailMessageSummary,
    GmailSearchResult,
    GmailMessageContent,
    GmailAttachment,
    GmailSendResult,
    GMAIL_SEARCH_RESULT_SCHEMA,
    GMAIL_MESSAGE_CONTENT_SCHEMA,
    GMAIL_SEND_RESULT_SCHEMA,
)

logger = logging.getLogger(__name__)

GMAIL_BATCH_SIZE = 25
GMAIL_REQUEST_DELAY = 0.1
HTML_BODY_TRUNCATE_LIMIT = 20000
GMAIL_METADATA_HEADERS = ["Subject", "From", "To", "Cc", "Message-ID", "Date"]


class _HTMLTextExtractor(HTMLParser):
    """Extract readable text from HTML using stdlib."""

    def __init__(self):
        super().__init__()
        self._text = []
        self._skip = False

    def handle_starttag(self, tag, attrs):
        self._skip = tag in ("script", "style")

    def handle_endtag(self, tag):
        if tag in ("script", "style"):
            self._skip = False

    def handle_data(self, data):
        if not self._skip:
            self._text.append(data)

    def get_text(self) -> str:
        return " ".join("".join(self._text).split())


def _html_to_text(html: str) -> str:
    """Convert HTML to readable plain text."""
    try:
        parser = _HTMLTextExtractor()
        parser.feed(html)
        return parser.get_text()
    except Exception:
        return html


def _extract_message_body(payload):
    """
    Helper function to extract plain text body from a Gmail message payload.
    (Maintained for backward compatibility)

    Args:
        payload (dict): The message payload from Gmail API

    Returns:
        str: The plain text body content, or empty string if not found
    """
    bodies = _extract_message_bodies(payload)
    return bodies.get("text", "")


def _extract_message_bodies(payload):
    """
    Helper function to extract both plain text and HTML bodies from a Gmail message payload.

    Args:
        payload (dict): The message payload from Gmail API

    Returns:
        dict: Dictionary with 'text' and 'html' keys containing body content
    """
    text_body = ""
    html_body = ""
    parts = [payload] if "parts" not in payload else payload.get("parts", [])

    part_queue = list(parts)  # Use a queue for BFS traversal of parts
    while part_queue:
        part = part_queue.pop(0)
        mime_type = part.get("mimeType", "")
        body_data = part.get("body", {}).get("data")

        if body_data:
            try:
                decoded_data = base64.urlsafe_b64decode(body_data).decode(
                    "utf-8", errors="ignore"
                )
                if mime_type == "text/plain" and not text_body:
                    text_body = decoded_data
                elif mime_type == "text/html" and not html_body:
                    html_body = decoded_data
            except Exception as e:
                logger.warning(f"Failed to decode body part: {e}")

        # Add sub-parts to queue for multipart messages
        if mime_type.startswith("multipart/") and "parts" in part:
            part_queue.extend(part.get("parts", []))

    # Check the main payload if it has body data directly
    if payload.get("body", {}).get("data"):
        try:
            decoded_data = base64.urlsafe_b64decode(payload["body"]["data"]).decode(
                "utf-8", errors="ignore"
            )
            mime_type = payload.get("mimeType", "")
            if mime_type == "text/plain" and not text_body:
                text_body = decoded_data
            elif mime_type == "text/html" and not html_body:
                html_body = decoded_data
        except Exception as e:
            logger.warning(f"Failed to decode main payload body: {e}")

    return {"text": text_body, "html": html_body}


def _format_body_content(text_body: str, html_body: str) -> str:
    """
    Helper function to format message body content with HTML fallback and truncation.
    Detects useless text/plain fallbacks (e.g., "Your client does not support HTML").

    Args:
        text_body: Plain text body content
        html_body: HTML body content

    Returns:
        Formatted body content string
    """
    text_stripped = text_body.strip()
    html_stripped = html_body.strip()

    # Detect useless fallback: HTML comments in text, or HTML is 50x+ longer
    use_html = html_stripped and (
        not text_stripped
        or "<!--" in text_stripped
        or len(html_stripped) > len(text_stripped) * 50
    )

    if use_html:
        content = _html_to_text(html_stripped)
        if len(content) > HTML_BODY_TRUNCATE_LIMIT:
            content = content[:HTML_BODY_TRUNCATE_LIMIT] + "\n\n[Content truncated...]"
        return content
    elif text_stripped:
        return text_body
    else:
        return "[No readable content found]"


def _extract_attachments(payload: dict) -> List[Dict[str, Any]]:
    """
    Extract attachment metadata from a Gmail message payload.

    Args:
        payload: The message payload from Gmail API

    Returns:
        List of attachment dictionaries with filename, mimeType, size, and attachmentId
    """
    attachments = []

    def search_parts(part):
        """Recursively search for attachments in message parts"""
        # Check if this part is an attachment
        if part.get("filename") and part.get("body", {}).get("attachmentId"):
            attachments.append(
                {
                    "filename": part["filename"],
                    "mimeType": part.get("mimeType", "application/octet-stream"),
                    "size": part.get("body", {}).get("size", 0),
                    "attachmentId": part["body"]["attachmentId"],
                }
            )

        # Recursively search sub-parts
        if "parts" in part:
            for subpart in part["parts"]:
                search_parts(subpart)

    # Start searching from the root payload
    search_parts(payload)
    return attachments


def _extract_headers(payload: dict, header_names: List[str]) -> Dict[str, str]:
    """
    Extract specified headers from a Gmail message payload.

    Args:
        payload: The message payload from Gmail API
        header_names: List of header names to extract

    Returns:
        Dict mapping header names to their values
    """
    headers = {}
    target_headers = {name.lower(): name for name in header_names}
    for header in payload.get("headers", []):
        header_name_lower = header["name"].lower()
        if header_name_lower in target_headers:
            # Store using the original requested casing
            headers[target_headers[header_name_lower]] = header["value"]
    return headers


def _prepare_gmail_message(
    subject: str,
    body: str,
    to: Optional[str] = None,
    cc: Optional[str] = None,
    bcc: Optional[str] = None,
    thread_id: Optional[str] = None,
    in_reply_to: Optional[str] = None,
    references: Optional[str] = None,
    body_format: Literal["plain", "html"] = "plain",
    from_email: Optional[str] = None,
    from_name: Optional[str] = None,
    attachments: Optional[List[Dict[str, str]]] = None,
) -> tuple[str, Optional[str]]:
    """
    Prepare a Gmail message with threading and attachment support.

    Args:
        subject: Email subject
        body: Email body content
        to: Optional recipient email address
        cc: Optional CC email address
        bcc: Optional BCC email address
        thread_id: Optional Gmail thread ID to reply within
        in_reply_to: Optional Message-ID of the message being replied to
        references: Optional chain of Message-IDs for proper threading
        body_format: Content type for the email body ('plain' or 'html')
        from_email: Optional sender email address
        from_name: Optional sender display name (e.g., "Peter Hartree")
        attachments: Optional list of attachments. Each can have 'path' (file path) OR 'content' (base64) + 'filename'

    Returns:
        Tuple of (raw_message, thread_id) where raw_message is base64 encoded
    """
    # Handle reply subject formatting
    reply_subject = subject
    if in_reply_to and not subject.lower().startswith("re:"):
        reply_subject = f"Re: {subject}"

    # Prepare the email
    normalized_format = body_format.lower()
    if normalized_format not in {"plain", "html"}:
        raise ValueError("body_format must be either 'plain' or 'html'.")

    # Use multipart if attachments are provided
    if attachments:
        message = MIMEMultipart()
        message.attach(MIMEText(body, normalized_format))

        # Process attachments
        for attachment in attachments:
            file_path = attachment.get("path")
            filename = attachment.get("filename")
            content_base64 = attachment.get("content")
            mime_type = attachment.get("mime_type")

            try:
                # If path is provided, read and encode the file
                if file_path:
                    path_obj = Path(file_path)
                    if not path_obj.exists():
                        logger.error(f"File not found: {file_path}")
                        continue

                    # Read file content
                    with open(path_obj, "rb") as f:
                        file_data = f.read()

                    # Use provided filename or extract from path
                    if not filename:
                        filename = path_obj.name

                    # Auto-detect MIME type if not provided
                    if not mime_type:
                        mime_type, _ = mimetypes.guess_type(str(path_obj))
                        if not mime_type:
                            mime_type = "application/octet-stream"

                # If content is provided (base64), decode it
                elif content_base64:
                    if not filename:
                        logger.warning("Skipping attachment: missing filename")
                        continue

                    file_data = base64.b64decode(content_base64)

                    if not mime_type:
                        mime_type = "application/octet-stream"

                else:
                    logger.warning("Skipping attachment: missing both path and content")
                    continue

                # Create MIME attachment
                main_type, sub_type = mime_type.split("/", 1)
                part = MIMEBase(main_type, sub_type)
                part.set_payload(file_data)
                encoders.encode_base64(part)

                # Sanitize filename to prevent header injection and ensure valid quoting
                safe_filename = (
                    (filename or "")
                    .replace("\r", "")
                    .replace("\n", "")
                    .replace("\\", "\\\\")
                    .replace('"', r"\"")
                )

                part.add_header(
                    "Content-Disposition", f'attachment; filename="{safe_filename}"'
                )

                message.attach(part)
                logger.info(f"Attached file: {filename} ({len(file_data)} bytes)")
            except Exception as e:
                logger.error(f"Failed to attach {filename or file_path}: {e}")
                continue
    else:
        message = MIMEText(body, normalized_format)

    message["Subject"] = reply_subject

    # Add sender if provided
    if from_email:
        if from_name:
            # Sanitize from_name to prevent header injection
            safe_name = (
                from_name.replace("\r", "").replace("\n", "").replace("\x00", "")
            )
            message["From"] = formataddr((safe_name, from_email))
        else:
            message["From"] = from_email

    # Add recipients if provided
    if to:
        message["To"] = to
    if cc:
        message["Cc"] = cc
    if bcc:
        message["Bcc"] = bcc

    # Add reply headers for threading
    if in_reply_to:
        message["In-Reply-To"] = in_reply_to

    if references:
        message["References"] = references

    # Encode message
    raw_message = base64.urlsafe_b64encode(message.as_bytes()).decode()

    return raw_message, thread_id


def _generate_gmail_web_url(item_id: str, account_index: int = 0) -> str:
    """
    Generate Gmail web interface URL for a message or thread ID.
    Uses #all to access messages from any Gmail folder/label (not just inbox).

    Args:
        item_id: Gmail message ID or thread ID
        account_index: Google account index (default 0 for primary account)

    Returns:
        Gmail web interface URL that opens the message/thread in Gmail web interface
    """
    return f"https://mail.google.com/mail/u/{account_index}/#all/{item_id}"


def _format_gmail_results_plain(
    messages: list, query: str, next_page_token: Optional[str] = None
) -> str:
    """Format Gmail search results in clean, LLM-friendly plain text."""
    if not messages:
        return f"No messages found for query: '{query}'"

    lines = [
        f"Found {len(messages)} messages matching '{query}':",
        "",
        "📧 MESSAGES:",
    ]

    for i, msg in enumerate(messages, 1):
        # Handle potential null/undefined message objects
        if not msg or not isinstance(msg, dict):
            lines.extend(
                [
                    f"  {i}. Message: Invalid message data",
                    "     Error: Message object is null or malformed",
                    "",
                ]
            )
            continue

        # Handle potential null/undefined values from Gmail API
        message_id = msg.get("id")
        thread_id = msg.get("threadId")

        # Convert None, empty string, or missing values to "unknown"
        if not message_id:
            message_id = "unknown"
        if not thread_id:
            thread_id = "unknown"

        if message_id != "unknown":
            message_url = _generate_gmail_web_url(message_id)
        else:
            message_url = "N/A"

        if thread_id != "unknown":
            thread_url = _generate_gmail_web_url(thread_id)
        else:
            thread_url = "N/A"

        lines.extend(
            [
                f"  {i}. Message ID: {message_id}",
                f"     Web Link: {message_url}",
                f"     Thread ID: {thread_id}",
                f"     Thread Link: {thread_url}",
                "",
            ]
        )

    lines.extend(
        [
            "💡 USAGE:",
            "  • Pass the Message IDs **as a list** to get_gmail_messages_content_batch()",
            "    e.g. get_gmail_messages_content_batch(message_ids=[...])",
            "  • Pass the Thread IDs to get_gmail_thread_content() (single) or get_gmail_threads_content_batch() (batch)",
        ]
    )

    # Add pagination info if there's a next page
    if next_page_token:
        lines.append("")
        lines.append(
            f"📄 PAGINATION: To get the next page, call search_gmail_messages again with page_token='{next_page_token}'"
        )

    return "\n".join(lines)


@server.tool(output_schema=GMAIL_SEARCH_RESULT_SCHEMA)
@handle_http_errors("search_gmail_messages", is_read_only=True, service_type="gmail")
@require_google_service("gmail", "gmail_read")
async def search_gmail_messages(
    service,
    query: str,
    page_size: int = 10,
    page_token: Optional[str] = None,
) -> ToolResult:
    """
    Searches messages in a user's Gmail account based on a query.
    Returns both Message IDs and Thread IDs for each found message, along with Gmail web interface links for manual verification.
    Supports pagination via page_token parameter.

    Args:
        query (str): The search query. Supports standard Gmail search operators.
        page_size (int): The maximum number of messages to return. Defaults to 10.
        page_token (Optional[str]): Token for retrieving the next page of results. Use the next_page_token from a previous response.

    Returns:
        ToolResult: LLM-friendly structured results with Message IDs, Thread IDs, and clickable Gmail web interface URLs for each found message.
        Includes pagination token if more results are available. Also includes structured_content for machine parsing.
    """
    logger.info(f"[search_gmail_messages] Query: '{query}', Page size: {page_size}")

    # Build the API request parameters
    request_params = {"userId": "me", "q": query, "maxResults": page_size}

    # Add page token if provided
    if page_token:
        request_params["pageToken"] = page_token
        logger.info("[search_gmail_messages] Using page_token for pagination")

    response = await asyncio.to_thread(
        service.users().messages().list(**request_params).execute
    )

    # Handle potential null response (but empty dict {} is valid)
    if response is None:
        logger.warning("[search_gmail_messages] Null response from Gmail API")
        return create_tool_result(
            text=f"No response received from Gmail API for query: '{query}'",
            data=GmailSearchResult(query=query, total_found=0, messages=[]),
        )

    messages = response.get("messages", [])
    # Additional safety check for null messages array
    if messages is None:
        messages = []

    # Extract next page token for pagination
    next_page_token = response.get("nextPageToken")

    # Build structured output
    message_summaries = []
    for msg in messages:
        if not msg or not isinstance(msg, dict):
            continue
        message_id = msg.get("id") or "unknown"
        thread_id = msg.get("threadId") or "unknown"
        message_summaries.append(
            GmailMessageSummary(
                message_id=message_id,
                thread_id=thread_id,
                web_link=_generate_gmail_web_url(message_id)
                if message_id != "unknown"
                else "N/A",
                thread_link=_generate_gmail_web_url(thread_id)
                if thread_id != "unknown"
                else "N/A",
            )
        )

    structured_result = GmailSearchResult(
        query=query,
        total_found=len(message_summaries),
        messages=message_summaries,
        next_page_token=next_page_token,
    )

    formatted_output = _format_gmail_results_plain(messages, query, next_page_token)

    logger.info(f"[search_gmail_messages] Found {len(messages)} messages")
    if next_page_token:
        logger.info(
            "[search_gmail_messages] More results available (next_page_token present)"
        )

    return create_tool_result(text=formatted_output, data=structured_result)


@server.tool(output_schema=GMAIL_MESSAGE_CONTENT_SCHEMA)
@handle_http_errors(
    "get_gmail_message_content", is_read_only=True, service_type="gmail"
)
@require_google_service("gmail", "gmail_read")
async def get_gmail_message_content(service, message_id: str) -> ToolResult:
    """
    Retrieves the full content (subject, sender, recipients, plain text body) of a specific Gmail message.

    Args:
        message_id (str): The unique ID of the Gmail message to retrieve.

    Returns:
        ToolResult: The message details including subject, sender, date, Message-ID, recipients (To, Cc), and body content.
        Also includes structured_content for machine parsing.
    """
    logger.info(f"[get_gmail_message_content] Invoked. Message ID: '{message_id}'")

    # Fetch message metadata first to get headers
    message_metadata = await asyncio.to_thread(
        service.users()
        .messages()
        .get(
            userId="me",
            id=message_id,
            format="metadata",
            metadataHeaders=GMAIL_METADATA_HEADERS,
        )
        .execute
    )

    headers = _extract_headers(
        message_metadata.get("payload", {}), GMAIL_METADATA_HEADERS
    )
    subject = headers.get("Subject", "(no subject)")
    sender = headers.get("From", "(unknown sender)")
    to = headers.get("To", "")
    cc = headers.get("Cc", "")
    date = headers.get("Date", "(unknown date)")
    rfc822_msg_id = headers.get("Message-ID", "")

    # Now fetch the full message to get the body parts
    message_full = await asyncio.to_thread(
        service.users()
        .messages()
        .get(
            userId="me",
            id=message_id,
            format="full",  # Request full payload for body
        )
        .execute
    )

    # Extract both text and HTML bodies using enhanced helper function
    payload = message_full.get("payload", {})
    bodies = _extract_message_bodies(payload)
    text_body = bodies.get("text", "")
    html_body = bodies.get("html", "")

    # Format body content with HTML fallback
    body_data = _format_body_content(text_body, html_body)

    # Extract attachment metadata
    attachments = _extract_attachments(payload)

    content_lines = [
        f"Subject: {subject}",
        f"From:    {sender}",
        f"Date:    {date}",
    ]

    if rfc822_msg_id:
        content_lines.append(f"Message-ID: {rfc822_msg_id}")

    if to:
        content_lines.append(f"To:      {to}")
    if cc:
        content_lines.append(f"Cc:      {cc}")

    content_lines.append(f"\n--- BODY ---\n{body_data or '[No text/plain body found]'}")

    # Add attachment information if present
    if attachments:
        content_lines.append("\n--- ATTACHMENTS ---")
        for i, att in enumerate(attachments, 1):
            size_kb = att["size"] / 1024
            content_lines.append(
                f"{i}. {att['filename']} ({att['mimeType']}, {size_kb:.1f} KB)\n"
                f"   Attachment ID: {att['attachmentId']}\n"
                f"   Use get_gmail_attachment_content(message_id='{message_id}', attachment_id='{att['attachmentId']}') to download"
            )

    # Build structured output
    structured_attachments = [
        GmailAttachment(
            filename=att["filename"],
            mime_type=att["mimeType"],
            size_bytes=att["size"],
            attachment_id=att["attachmentId"],
        )
        for att in attachments
    ]

    structured_result = GmailMessageContent(
        message_id=message_id,
        subject=subject,
        sender=sender,
        date=date,
        to=to if to else None,
        cc=cc if cc else None,
        rfc822_message_id=rfc822_msg_id if rfc822_msg_id else None,
        body=body_data or "",
        attachments=structured_attachments,
    )

    return create_tool_result(text="\n".join(content_lines), data=structured_result)


@server.tool()
@handle_http_errors(
    "get_gmail_messages_content_batch", is_read_only=True, service_type="gmail"
)
@require_google_service("gmail", "gmail_read")
async def get_gmail_messages_content_batch(
    service,
    message_ids: List[str],
    format: Literal["full", "metadata"] = "full",
) -> str:
    """
    Retrieves the content of multiple Gmail messages in a single batch request.
    Supports up to 25 messages per batch to prevent SSL connection exhaustion.

    Args:
        message_ids (List[str]): List of Gmail message IDs to retrieve (max 25 per batch).
        format (Literal["full", "metadata"]): Message format. "full" includes body, "metadata" only headers.

    Returns:
        str: A formatted list of message contents including subject, sender, date, Message-ID, recipients (To, Cc), and body (if full format).
    """
    logger.info(
        f"[get_gmail_messages_content_batch] Invoked. Message count: {len(message_ids)}"
    )

    if not message_ids:
        raise Exception("No message IDs provided")

    output_messages = []

    # Process in smaller chunks to prevent SSL connection exhaustion
    for chunk_start in range(0, len(message_ids), GMAIL_BATCH_SIZE):
        chunk_ids = message_ids[chunk_start : chunk_start + GMAIL_BATCH_SIZE]
        results: Dict[str, Dict] = {}

        def _batch_callback(request_id, response, exception):
            """Callback for batch requests"""
            results[request_id] = {"data": response, "error": exception}

        # Try to use batch API
        try:
            batch = service.new_batch_http_request(callback=_batch_callback)

            for mid in chunk_ids:
                if format == "metadata":
                    req = (
                        service.users()
                        .messages()
                        .get(
                            userId="me",
                            id=mid,
                            format="metadata",
                            metadataHeaders=GMAIL_METADATA_HEADERS,
                        )
                    )
                else:
                    req = (
                        service.users()
                        .messages()
                        .get(userId="me", id=mid, format="full")
                    )
                batch.add(req, request_id=mid)

            # Execute batch request
            await asyncio.to_thread(batch.execute)

        except Exception as batch_error:
            # Fallback to sequential processing instead of parallel to prevent SSL exhaustion
            logger.warning(
                f"[get_gmail_messages_content_batch] Batch API failed, falling back to sequential processing: {batch_error}"
            )

            async def fetch_message_with_retry(mid: str, max_retries: int = 3):
                """Fetch a single message with exponential backoff retry for SSL errors"""
                for attempt in range(max_retries):
                    try:
                        if format == "metadata":
                            msg = await asyncio.to_thread(
                                service.users()
                                .messages()
                                .get(
                                    userId="me",
                                    id=mid,
                                    format="metadata",
                                    metadataHeaders=GMAIL_METADATA_HEADERS,
                                )
                                .execute
                            )
                        else:
                            msg = await asyncio.to_thread(
                                service.users()
                                .messages()
                                .get(userId="me", id=mid, format="full")
                                .execute
                            )
                        return mid, msg, None
                    except ssl.SSLError as ssl_error:
                        if attempt < max_retries - 1:
                            # Exponential backoff: 1s, 2s, 4s
                            delay = 2**attempt
                            logger.warning(
                                f"[get_gmail_messages_content_batch] SSL error for message {mid} on attempt {attempt + 1}: {ssl_error}. Retrying in {delay}s..."
                            )
                            await asyncio.sleep(delay)
                        else:
                            logger.error(
                                f"[get_gmail_messages_content_batch] SSL error for message {mid} on final attempt: {ssl_error}"
                            )
                            return mid, None, ssl_error
                    except Exception as e:
                        return mid, None, e

            # Process messages sequentially with small delays to prevent connection exhaustion
            for mid in chunk_ids:
                mid_result, msg_data, error = await fetch_message_with_retry(mid)
                results[mid_result] = {"data": msg_data, "error": error}
                # Brief delay between requests to allow connection cleanup
                await asyncio.sleep(GMAIL_REQUEST_DELAY)

        # Process results for this chunk
        for mid in chunk_ids:
            entry = results.get(mid, {"data": None, "error": "No result"})

            if entry["error"]:
                output_messages.append(f"⚠️ Message {mid}: {entry['error']}\n")
            else:
                message = entry["data"]
                if not message:
                    output_messages.append(f"⚠️ Message {mid}: No data returned\n")
                    continue

                # Extract content based on format
                payload = message.get("payload", {})

                if format == "metadata":
                    headers = _extract_headers(payload, GMAIL_METADATA_HEADERS)
                    subject = headers.get("Subject", "(no subject)")
                    sender = headers.get("From", "(unknown sender)")
                    to = headers.get("To", "")
                    cc = headers.get("Cc", "")
                    rfc822_msg_id = headers.get("Message-ID", "")

                    msg_output = (
                        f"Message ID: {mid}\nSubject: {subject}\nFrom: {sender}\n"
                        f"Date: {headers.get('Date', '(unknown date)')}\n"
                    )
                    if rfc822_msg_id:
                        msg_output += f"Message-ID: {rfc822_msg_id}\n"

                    if to:
                        msg_output += f"To: {to}\n"
                    if cc:
                        msg_output += f"Cc: {cc}\n"
                    msg_output += f"Web Link: {_generate_gmail_web_url(mid)}\n"

                    output_messages.append(msg_output)
                else:
                    # Full format - extract body too
                    headers = _extract_headers(payload, GMAIL_METADATA_HEADERS)
                    subject = headers.get("Subject", "(no subject)")
                    sender = headers.get("From", "(unknown sender)")
                    to = headers.get("To", "")
                    cc = headers.get("Cc", "")
                    rfc822_msg_id = headers.get("Message-ID", "")

                    # Extract both text and HTML bodies using enhanced helper function
                    bodies = _extract_message_bodies(payload)
                    text_body = bodies.get("text", "")
                    html_body = bodies.get("html", "")

                    # Format body content with HTML fallback
                    body_data = _format_body_content(text_body, html_body)

                    msg_output = (
                        f"Message ID: {mid}\nSubject: {subject}\nFrom: {sender}\n"
                        f"Date: {headers.get('Date', '(unknown date)')}\n"
                    )
                    if rfc822_msg_id:
                        msg_output += f"Message-ID: {rfc822_msg_id}\n"

                    if to:
                        msg_output += f"To: {to}\n"
                    if cc:
                        msg_output += f"Cc: {cc}\n"
                    msg_output += (
                        f"Web Link: {_generate_gmail_web_url(mid)}\n\n{body_data}\n"
                    )

                    output_messages.append(msg_output)

    # Combine all messages with separators
    final_output = f"Retrieved {len(message_ids)} messages:\n\n"
    final_output += "\n---\n\n".join(output_messages)

    return final_output


@server.tool()
@handle_http_errors(
    "get_gmail_attachment_content", is_read_only=True, service_type="gmail"
)
@require_google_service("gmail", "gmail_read")
async def get_gmail_attachment_content(
    service,
    message_id: str,
    attachment_id: str,
) -> str:
    """
    Downloads the content of a specific email attachment.

    Args:
        message_id (str): The ID of the Gmail message containing the attachment.
        attachment_id (str): The ID of the attachment to download.

    Returns:
        str: Attachment metadata and base64-encoded content that can be decoded and saved.
    """
    logger.info(f"[get_gmail_attachment_content] Invoked. Message ID: '{message_id}'")

    # Download attachment directly without refetching message metadata.
    #
    # Important: Gmail attachment IDs are ephemeral and change between API calls for the
    # same message. If we refetch the message here to get metadata, the new attachment IDs
    # won't match the attachment_id parameter provided by the caller, causing the function
    # to fail. The attachment download endpoint returns size information, and filename/mime
    # type should be obtained from the original message content call that provided this ID.
    try:
        attachment = await asyncio.to_thread(
            service.users()
            .messages()
            .attachments()
            .get(userId="me", messageId=message_id, id=attachment_id)
            .execute
        )
    except Exception as e:
        logger.error(
            f"[get_gmail_attachment_content] Failed to download attachment: {e}"
        )
        return (
            f"Error: Failed to download attachment. The attachment ID may have changed.\n"
            f"Please fetch the message content again to get an updated attachment ID.\n\n"
            f"Error details: {str(e)}"
        )

    # Format response with attachment data
    size_bytes = attachment.get("size", 0)
    size_kb = size_bytes / 1024 if size_bytes else 0
    base64_data = attachment.get("data", "")

    # Check if we're in stateless mode (can't save files)
    from auth.oauth_config import is_stateless_mode

    if is_stateless_mode():
        result_lines = [
            "Attachment downloaded successfully!",
            f"Message ID: {message_id}",
            f"Size: {size_kb:.1f} KB ({size_bytes} bytes)",
            "\n⚠️ Stateless mode: File storage disabled.",
            "\nBase64-encoded content (first 100 characters shown):",
            f"{base64_data[:100]}...",
            "\nNote: Attachment IDs are ephemeral. Always use IDs from the most recent message fetch.",
        ]
        logger.info(
            f"[get_gmail_attachment_content] Successfully downloaded {size_kb:.1f} KB attachment (stateless mode)"
        )
        return "\n".join(result_lines)

    # Save attachment and generate URL
    try:
        from core.attachment_storage import get_attachment_storage, get_attachment_url

        storage = get_attachment_storage()

        # Try to get filename and mime type from message (optional - attachment IDs are ephemeral)
        filename = None
        mime_type = None
        try:
            # Quick metadata fetch to try to get attachment info
            # Note: This might fail if attachment IDs changed, but worth trying
            message_metadata = await asyncio.to_thread(
                service.users()
                .messages()
                .get(userId="me", id=message_id, format="metadata")
                .execute
            )
            payload = message_metadata.get("payload", {})
            attachments = _extract_attachments(payload)
            for att in attachments:
                if att.get("attachmentId") == attachment_id:
                    filename = att.get("filename")
                    mime_type = att.get("mimeType")
                    break
        except Exception:
            # If we can't get metadata, use defaults
            logger.debug(
                f"Could not fetch attachment metadata for {attachment_id}, using defaults"
            )

        # Save attachment
        file_id = storage.save_attachment(
            base64_data=base64_data, filename=filename, mime_type=mime_type
        )

        # Generate URL
        attachment_url = get_attachment_url(file_id)

        result_lines = [
            "Attachment downloaded successfully!",
            f"Message ID: {message_id}",
            f"Size: {size_kb:.1f} KB ({size_bytes} bytes)",
            f"\n📎 Download URL: {attachment_url}",
            "\nThe attachment has been saved and is available at the URL above.",
            "The file will expire after 1 hour.",
            "\nNote: Attachment IDs are ephemeral. Always use IDs from the most recent message fetch.",
        ]

        logger.info(
            f"[get_gmail_attachment_content] Successfully saved {size_kb:.1f} KB attachment as {file_id}"
        )
        return "\n".join(result_lines)

    except Exception as e:
        logger.error(
            f"[get_gmail_attachment_content] Failed to save attachment: {e}",
            exc_info=True,
        )
        # Fallback to showing base64 preview
        result_lines = [
            "Attachment downloaded successfully!",
            f"Message ID: {message_id}",
            f"Size: {size_kb:.1f} KB ({size_bytes} bytes)",
            "\n⚠️ Failed to save attachment file. Showing preview instead.",
            "\nBase64-encoded content (first 100 characters shown):",
            f"{base64_data[:100]}...",
            f"\nError: {str(e)}",
            "\nNote: Attachment IDs are ephemeral. Always use IDs from the most recent message fetch.",
        ]
        return "\n".join(result_lines)


@server.tool(output_schema=GMAIL_SEND_RESULT_SCHEMA)
@handle_http_errors("send_gmail_message", service_type="gmail")
@require_google_service("gmail", GMAIL_SEND_SCOPE)
async def send_gmail_message(
    service,
    to: str = Body(..., description="Recipient email address."),
    subject: str = Body(..., description="Email subject."),
    body: str = Body(..., description="Email body content (plain text or HTML)."),
    body_format: Literal["plain", "html"] = Body(
        "plain",
        description="Email body format. Use 'plain' for plaintext or 'html' for HTML content.",
    ),
    cc: Optional[str] = Body(None, description="Optional CC email address."),
    bcc: Optional[str] = Body(None, description="Optional BCC email address."),
    from_name: Optional[str] = Body(
        None,
        description="Optional sender display name (e.g., 'Peter Hartree'). If provided, the From header will be formatted as 'Name <email>'.",
    ),
    from_email: Optional[str] = Body(
        None,
        description="Optional 'Send As' alias email address. Must be configured in Gmail settings (Settings > Accounts > Send mail as). If not provided, uses the authenticated user's email.",
    ),
    thread_id: Optional[str] = Body(
        None, description="Optional Gmail thread ID to reply within."
    ),
    in_reply_to: Optional[str] = Body(
        None, description="Optional Message-ID of the message being replied to."
    ),
    references: Optional[str] = Body(
        None, description="Optional chain of Message-IDs for proper threading."
    ),
    attachments: Optional[List[Dict[str, str]]] = Body(
        None,
        description='Optional list of attachments. Each can have: "path" (file path, auto-encodes), OR "content" (standard base64, not urlsafe) + "filename". Optional "mime_type". Example: [{"path": "/path/to/file.pdf"}] or [{"filename": "doc.pdf", "content": "base64data", "mime_type": "application/pdf"}]',
    ),
) -> ToolResult:
    """
    Sends an email using the user's Gmail account. Supports both new emails and replies with optional attachments.
    Supports Gmail's "Send As" feature to send from configured alias addresses.

    Args:
        to (str): Recipient email address.
        subject (str): Email subject.
        body (str): Email body content.
        body_format (Literal['plain', 'html']): Email body format. Defaults to 'plain'.
        attachments (Optional[List[Dict[str, str]]]): Optional list of attachments. Each dict can contain:
            Option 1 - File path (auto-encodes):
              - 'path' (required): File path to attach
              - 'filename' (optional): Override filename
              - 'mime_type' (optional): Override MIME type (auto-detected if not provided)
            Option 2 - Base64 content:
              - 'content' (required): Standard base64-encoded file content (not urlsafe)
              - 'filename' (required): Name of the file
              - 'mime_type' (optional): MIME type (defaults to 'application/octet-stream')
        cc (Optional[str]): Optional CC email address.
        bcc (Optional[str]): Optional BCC email address.
        from_name (Optional[str]): Optional sender display name. If provided, the From header will be formatted as 'Name <email>'.
        from_email (Optional[str]): Optional 'Send As' alias email address. The alias must be
            configured in Gmail settings (Settings > Accounts > Send mail as). If not provided,
            the email will be sent from the authenticated user's primary email address.
        thread_id (Optional[str]): Optional Gmail thread ID to reply within. When provided, sends a reply.
        in_reply_to (Optional[str]): Optional Message-ID of the message being replied to. Used for proper threading.
        references (Optional[str]): Optional chain of Message-IDs for proper threading. Should include all previous Message-IDs.

    Returns:
        ToolResult: Confirmation message with the sent email's message ID.
        Also includes structured_content for machine parsing.

    Examples:
        # Send a new email
        send_gmail_message(to="user@example.com", subject="Hello", body="Hi there!")

        # Send with a custom display name
        send_gmail_message(to="user@example.com", subject="Hello", body="Hi there!", from_name="John Doe")

        # Send an HTML email
        send_gmail_message(
            to="user@example.com",
            subject="Hello",
            body="<strong>Hi there!</strong>",
            body_format="html"
        )

        # Send from a configured alias (Send As)
        send_gmail_message(
            to="user@example.com",
            subject="Business Inquiry",
            body="Hello from my business address...",
            from_email="business@mydomain.com"
        )

        # Send an email with CC and BCC
        send_gmail_message(
            to="user@example.com",
            cc="manager@example.com",
            bcc="archive@example.com",
            subject="Project Update",
            body="Here's the latest update..."
        )

        # Send an email with attachments (using file path)
        send_gmail_message(
            to="user@example.com",
            subject="Report",
            body="Please see attached report.",
            attachments=[{
                "path": "/path/to/report.pdf"
            }]
        )

        # Send an email with attachments (using base64 content)
        send_gmail_message(
            to="user@example.com",
            subject="Report",
            body="Please see attached report.",
            attachments=[{
                "filename": "report.pdf",
                "content": "JVBERi0xLjQK...",  # base64 encoded PDF
                "mime_type": "application/pdf"
            }]
        )

        # Send a reply
        send_gmail_message(
            to="user@example.com",
            subject="Re: Meeting tomorrow",
            body="Thanks for the update!",
            thread_id="thread_123",
            in_reply_to="<message123@gmail.com>",
            references="<original@gmail.com> <message123@gmail.com>"
        )
    """
    logger.info(
        f"[send_gmail_message] Invoked. Subject: '{subject}', Attachments: {len(attachments) if attachments else 0}"
    )

    # Prepare the email message
    raw_message, thread_id_final = _prepare_gmail_message(
        subject=subject,
        body=body,
        to=to,
        cc=cc,
        bcc=bcc,
        thread_id=thread_id,
        in_reply_to=in_reply_to,
        references=references,
        body_format=body_format,
        from_email=from_email,
        from_name=from_name,
        attachments=attachments if attachments else None,
    )

    send_body = {"raw": raw_message}

    # Associate with thread if provided
    if thread_id_final:
        send_body["threadId"] = thread_id_final

    # Send the message
    sent_message = await asyncio.to_thread(
        service.users().messages().send(userId="me", body=send_body).execute
    )
    message_id = sent_message.get("id")
    result_thread_id = sent_message.get("threadId")
    attachment_count = len(attachments) if attachments else 0

    # Build text output
    if attachment_count > 0:
        text_output = f"Email sent with {attachment_count} attachment(s)! Message ID: {message_id}"
    else:
        text_output = f"Email sent! Message ID: {message_id}"

    # Build structured output
    structured_result = GmailSendResult(
        message_id=message_id,
        thread_id=result_thread_id,
        attachment_count=attachment_count,
    )

    return create_tool_result(text=text_output, data=structured_result)


@server.tool()
@handle_http_errors("draft_gmail_message", service_type="gmail")
@require_google_service("gmail", GMAIL_COMPOSE_SCOPE)
async def draft_gmail_message(
    service,
    subject: str = Body(..., description="Email subject."),
    body: str = Body(..., description="Email body (plain text)."),
    body_format: Literal["plain", "html"] = Body(
        "plain",
        description="Email body format. Use 'plain' for plaintext or 'html' for HTML content.",
    ),
    to: Optional[str] = Body(None, description="Optional recipient email address."),
    cc: Optional[str] = Body(None, description="Optional CC email address."),
    bcc: Optional[str] = Body(None, description="Optional BCC email address."),
    from_name: Optional[str] = Body(
        None,
        description="Optional sender display name (e.g., 'Peter Hartree'). If provided, the From header will be formatted as 'Name <email>'.",
    ),
    from_email: Optional[str] = Body(
        None,
        description="Optional 'Send As' alias email address. Must be configured in Gmail settings (Settings > Accounts > Send mail as). If not provided, uses the authenticated user's email.",
    ),
    thread_id: Optional[str] = Body(
        None, description="Optional Gmail thread ID to reply within."
    ),
    in_reply_to: Optional[str] = Body(
        None, description="Optional Message-ID of the message being replied to."
    ),
    references: Optional[str] = Body(
        None, description="Optional chain of Message-IDs for proper threading."
    ),
    attachments: Optional[List[Dict[str, str]]] = Body(
        None,
        description="Optional list of attachments. Each can have: 'path' (file path, auto-encodes), OR 'content' (standard base64, not urlsafe) + 'filename'. Optional 'mime_type' (auto-detected from path if not provided).",
    ),
) -> str:
    """
    Creates a draft email in the user's Gmail account. Supports both new drafts and reply drafts with optional attachments.
    Supports Gmail's "Send As" feature to draft from configured alias addresses.

    Args:
        subject (str): Email subject.
        body (str): Email body (plain text).
        body_format (Literal['plain', 'html']): Email body format. Defaults to 'plain'.
        to (Optional[str]): Optional recipient email address. Can be left empty for drafts.
        cc (Optional[str]): Optional CC email address.
        bcc (Optional[str]): Optional BCC email address.
        from_name (Optional[str]): Optional sender display name. If provided, the From header will be formatted as 'Name <email>'.
        from_email (Optional[str]): Optional 'Send As' alias email address. The alias must be
            configured in Gmail settings (Settings > Accounts > Send mail as). If not provided,
            the draft will be from the authenticated user's primary email address.
        thread_id (Optional[str]): Optional Gmail thread ID to reply within. When provided, creates a reply draft.
        in_reply_to (Optional[str]): Optional Message-ID of the message being replied to. Used for proper threading.
        references (Optional[str]): Optional chain of Message-IDs for proper threading. Should include all previous Message-IDs.
        attachments (List[Dict[str, str]]): Optional list of attachments. Each dict can contain:
            Option 1 - File path (auto-encodes):
              - 'path' (required): File path to attach
              - 'filename' (optional): Override filename
              - 'mime_type' (optional): Override MIME type (auto-detected if not provided)
            Option 2 - Base64 content:
              - 'content' (required): Standard base64-encoded file content (not urlsafe)
              - 'filename' (required): Name of the file
              - 'mime_type' (optional): MIME type (defaults to 'application/octet-stream')

    Returns:
        str: Confirmation message with the created draft's ID.

    Examples:
        # Create a new draft
        draft_gmail_message(subject="Hello", body="Hi there!", to="user@example.com")

        # Create a draft from a configured alias (Send As)
        draft_gmail_message(
            subject="Business Inquiry",
            body="Hello from my business address...",
            to="user@example.com",
            from_email="business@mydomain.com"
        )

        # Create a plaintext draft with CC and BCC
        draft_gmail_message(
            subject="Project Update",
            body="Here's the latest update...",
            to="user@example.com",
            cc="manager@example.com",
            bcc="archive@example.com"
        )

        # Create a HTML draft with CC and BCC
        draft_gmail_message(
            subject="Project Update",
            body="<strong>Hi there!</strong>",
            body_format="html",
            to="user@example.com",
            cc="manager@example.com",
            bcc="archive@example.com"
        )

        # Create a reply draft in plaintext
        draft_gmail_message(
            subject="Re: Meeting tomorrow",
            body="Thanks for the update!",
            to="user@example.com",
            thread_id="thread_123",
            in_reply_to="<message123@gmail.com>",
            references="<original@gmail.com> <message123@gmail.com>"
        )

        # Create a reply draft in HTML
        draft_gmail_message(
            subject="Re: Meeting tomorrow",
            body="<strong>Thanks for the update!</strong>",
            body_format="html",
            to="user@example.com",
            thread_id="thread_123",
            in_reply_to="<message123@gmail.com>",
            references="<original@gmail.com> <message123@gmail.com>"
        )
    """
    logger.info(f"[draft_gmail_message] Invoked. Subject: '{subject}'")

    # Prepare the email message
    raw_message, thread_id_final = _prepare_gmail_message(
        subject=subject,
        body=body,
        body_format=body_format,
        to=to,
        cc=cc,
        bcc=bcc,
        thread_id=thread_id,
        in_reply_to=in_reply_to,
        references=references,
        from_email=from_email,
        from_name=from_name,
        attachments=attachments,
    )

    # Create a draft instead of sending
    draft_body = {"message": {"raw": raw_message}}

    # Associate with thread if provided
    if thread_id_final:
        draft_body["message"]["threadId"] = thread_id_final

    # Create the draft
    created_draft = await asyncio.to_thread(
        service.users().drafts().create(userId="me", body=draft_body).execute
    )
    draft_id = created_draft.get("id")
    attachment_info = f" with {len(attachments)} attachment(s)" if attachments else ""
    return f"Draft created{attachment_info}! Draft ID: {draft_id}"


def _format_thread_content(thread_data: dict, thread_id: str) -> str:
    """
    Helper function to format thread content from Gmail API response.

    Args:
        thread_data (dict): Thread data from Gmail API
        thread_id (str): Thread ID for display

    Returns:
        str: Formatted thread content
    """
    messages = thread_data.get("messages", [])
    if not messages:
        return f"No messages found in thread '{thread_id}'."

    # Extract thread subject from the first message
    first_message = messages[0]
    first_headers = {
        h["name"]: h["value"]
        for h in first_message.get("payload", {}).get("headers", [])
    }
    thread_subject = first_headers.get("Subject", "(no subject)")

    # Build the thread content
    content_lines = [
        f"Thread ID: {thread_id}",
        f"Subject: {thread_subject}",
        f"Messages: {len(messages)}",
        "",
    ]

    # Process each message in the thread
    for i, message in enumerate(messages, 1):
        # Extract headers
        headers = {
            h["name"]: h["value"] for h in message.get("payload", {}).get("headers", [])
        }

        sender = headers.get("From", "(unknown sender)")
        date = headers.get("Date", "(unknown date)")
        subject = headers.get("Subject", "(no subject)")

        # Extract both text and HTML bodies
        payload = message.get("payload", {})
        bodies = _extract_message_bodies(payload)
        text_body = bodies.get("text", "")
        html_body = bodies.get("html", "")

        # Format body content with HTML fallback
        body_data = _format_body_content(text_body, html_body)

        # Add message to content
        content_lines.extend(
            [
                f"=== Message {i} ===",
                f"From: {sender}",
                f"Date: {date}",
            ]
        )

        # Only show subject if it's different from thread subject
        if subject != thread_subject:
            content_lines.append(f"Subject: {subject}")

        content_lines.extend(
            [
                "",
                body_data,
                "",
            ]
        )

    return "\n".join(content_lines)


@server.tool()
@require_google_service("gmail", "gmail_read")
@handle_http_errors("get_gmail_thread_content", is_read_only=True, service_type="gmail")
async def get_gmail_thread_content(service, thread_id: str) -> str:
    """
    Retrieves the complete content of a Gmail conversation thread, including all messages.

    Args:
        thread_id (str): The unique ID of the Gmail thread to retrieve.

    Returns:
        str: The complete thread content with all messages formatted for reading.
    """
    logger.info(f"[get_gmail_thread_content] Invoked. Thread ID: '{thread_id}'")

    # Fetch the complete thread with all messages
    thread_response = await asyncio.to_thread(
        service.users().threads().get(userId="me", id=thread_id, format="full").execute
    )

    return _format_thread_content(thread_response, thread_id)


@server.tool()
@require_google_service("gmail", "gmail_read")
@handle_http_errors(
    "get_gmail_threads_content_batch", is_read_only=True, service_type="gmail"
)
async def get_gmail_threads_content_batch(
    service,
    thread_ids: List[str],
) -> str:
    """
    Retrieves the content of multiple Gmail threads in a single batch request.
    Supports up to 25 threads per batch to prevent SSL connection exhaustion.

    Args:
        thread_ids (List[str]): A list of Gmail thread IDs to retrieve. The function will automatically batch requests in chunks of 25.

    Returns:
        str: A formatted list of thread contents with separators.
    """
    logger.info(
        f"[get_gmail_threads_content_batch] Invoked. Thread count: {len(thread_ids)}"
    )

    if not thread_ids:
        raise ValueError("No thread IDs provided")

    output_threads = []

    def _batch_callback(request_id, response, exception):
        """Callback for batch requests"""
        results[request_id] = {"data": response, "error": exception}

    # Process in smaller chunks to prevent SSL connection exhaustion
    for chunk_start in range(0, len(thread_ids), GMAIL_BATCH_SIZE):
        chunk_ids = thread_ids[chunk_start : chunk_start + GMAIL_BATCH_SIZE]
        results: Dict[str, Dict] = {}

        # Try to use batch API
        try:
            batch = service.new_batch_http_request(callback=_batch_callback)

            for tid in chunk_ids:
                req = service.users().threads().get(userId="me", id=tid, format="full")
                batch.add(req, request_id=tid)

            # Execute batch request
            await asyncio.to_thread(batch.execute)

        except Exception as batch_error:
            # Fallback to sequential processing instead of parallel to prevent SSL exhaustion
            logger.warning(
                f"[get_gmail_threads_content_batch] Batch API failed, falling back to sequential processing: {batch_error}"
            )

            async def fetch_thread_with_retry(tid: str, max_retries: int = 3):
                """Fetch a single thread with exponential backoff retry for SSL errors"""
                for attempt in range(max_retries):
                    try:
                        thread = await asyncio.to_thread(
                            service.users()
                            .threads()
                            .get(userId="me", id=tid, format="full")
                            .execute
                        )
                        return tid, thread, None
                    except ssl.SSLError as ssl_error:
                        if attempt < max_retries - 1:
                            # Exponential backoff: 1s, 2s, 4s
                            delay = 2**attempt
                            logger.warning(
                                f"[get_gmail_threads_content_batch] SSL error for thread {tid} on attempt {attempt + 1}: {ssl_error}. Retrying in {delay}s..."
                            )
                            await asyncio.sleep(delay)
                        else:
                            logger.error(
                                f"[get_gmail_threads_content_batch] SSL error for thread {tid} on final attempt: {ssl_error}"
                            )
                            return tid, None, ssl_error
                    except Exception as e:
                        return tid, None, e

            # Process threads sequentially with small delays to prevent connection exhaustion
            for tid in chunk_ids:
                tid_result, thread_data, error = await fetch_thread_with_retry(tid)
                results[tid_result] = {"data": thread_data, "error": error}
                # Brief delay between requests to allow connection cleanup
                await asyncio.sleep(GMAIL_REQUEST_DELAY)

        # Process results for this chunk
        for tid in chunk_ids:
            entry = results.get(tid, {"data": None, "error": "No result"})

            if entry["error"]:
                output_threads.append(f"⚠️ Thread {tid}: {entry['error']}\n")
            else:
                thread = entry["data"]
                if not thread:
                    output_threads.append(f"⚠️ Thread {tid}: No data returned\n")
                    continue

                output_threads.append(_format_thread_content(thread, tid))

    # Combine all threads with separators
    header = f"Retrieved {len(thread_ids)} threads:"
    return header + "\n\n" + "\n---\n\n".join(output_threads)


@server.tool()
@handle_http_errors("get_gmail_user_email", is_read_only=True, service_type="gmail")
@require_google_service("gmail", "gmail_read")
async def get_gmail_user_email(service) -> str:
    """
    Retrieves the email address of the currently authenticated Gmail user.

    Returns:
        str: The user's email address.
    """
    logger.info("[get_gmail_user_email] Invoked")

    profile = await asyncio.to_thread(service.users().getProfile(userId="me").execute)

    email = profile.get("emailAddress", "")
    if not email:
        return "Unable to retrieve user email address."

    return f"Current user email: {email}"


@server.tool()
@handle_http_errors("list_gmail_labels", is_read_only=True, service_type="gmail")
@require_google_service("gmail", "gmail_read")
async def list_gmail_labels(service) -> str:
    """
    Lists all labels in the user's Gmail account.

    Returns:
        str: A formatted list of all labels with their IDs, names, and types.
    """
    logger.info("[list_gmail_labels] Invoked")

    response = await asyncio.to_thread(
        service.users().labels().list(userId="me").execute
    )
    labels = response.get("labels", [])

    if not labels:
        return "No labels found."

    lines = [f"Found {len(labels)} labels:", ""]

    system_labels = []
    user_labels = []

    for label in labels:
        if label.get("type") == "system":
            system_labels.append(label)
        else:
            user_labels.append(label)

    if system_labels:
        lines.append("📂 SYSTEM LABELS:")
        for label in system_labels:
            lines.append(f"  • {label['name']} (ID: {label['id']})")
        lines.append("")

    if user_labels:
        lines.append("🏷️  USER LABELS:")
        for label in user_labels:
            lines.append(f"  • {label['name']} (ID: {label['id']})")

    return "\n".join(lines)


@server.tool()
@handle_http_errors("manage_gmail_label", service_type="gmail")
@require_google_service("gmail", GMAIL_LABELS_SCOPE)
async def manage_gmail_label(
    service,
    action: Literal["create", "update", "delete"],
    name: Optional[str] = None,
    label_id: Optional[str] = None,
    label_list_visibility: Literal["labelShow", "labelHide"] = "labelShow",
    message_list_visibility: Literal["show", "hide"] = "show",
) -> str:
    """
    Manages Gmail labels: create, update, or delete labels.

    Args:
        action (Literal["create", "update", "delete"]): Action to perform on the label.
        name (Optional[str]): Label name. Required for create, optional for update.
        label_id (Optional[str]): Label ID. Required for update and delete operations.
        label_list_visibility (Literal["labelShow", "labelHide"]): Whether the label is shown in the label list.
        message_list_visibility (Literal["show", "hide"]): Whether the label is shown in the message list.

    Returns:
        str: Confirmation message of the label operation.
    """
    logger.info(f"[manage_gmail_label] Invoked. Action: '{action}'")

    if action == "create" and not name:
        raise Exception("Label name is required for create action.")

    if action in ["update", "delete"] and not label_id:
        raise Exception("Label ID is required for update and delete actions.")

    if action == "create":
        label_object = {
            "name": name,
            "labelListVisibility": label_list_visibility,
            "messageListVisibility": message_list_visibility,
        }
        created_label = await asyncio.to_thread(
            service.users().labels().create(userId="me", body=label_object).execute
        )
        return f"Label created successfully!\nName: {created_label['name']}\nID: {created_label['id']}"

    elif action == "update":
        current_label = await asyncio.to_thread(
            service.users().labels().get(userId="me", id=label_id).execute
        )

        label_object = {
            "id": label_id,
            "name": name if name is not None else current_label["name"],
            "labelListVisibility": label_list_visibility,
            "messageListVisibility": message_list_visibility,
        }

        updated_label = await asyncio.to_thread(
            service.users()
            .labels()
            .update(userId="me", id=label_id, body=label_object)
            .execute
        )
        return f"Label updated successfully!\nName: {updated_label['name']}\nID: {updated_label['id']}"

    elif action == "delete":
        label = await asyncio.to_thread(
            service.users().labels().get(userId="me", id=label_id).execute
        )
        label_name = label["name"]

        await asyncio.to_thread(
            service.users().labels().delete(userId="me", id=label_id).execute
        )
        return f"Label '{label_name}' (ID: {label_id}) deleted successfully!"


@server.tool()
@handle_http_errors("list_gmail_filters", is_read_only=True, service_type="gmail")
@require_google_service("gmail", "gmail_settings_basic")
async def list_gmail_filters(service) -> str:
    """
    Lists all Gmail filters configured in the user's mailbox.

    Returns:
        str: A formatted list of filters with their criteria and actions.
    """
    logger.info("[list_gmail_filters] Invoked")

    response = await asyncio.to_thread(
        service.users().settings().filters().list(userId="me").execute
    )

    filters = response.get("filter") or response.get("filters") or []

    if not filters:
        return "No filters found."

    lines = [f"Found {len(filters)} filters:", ""]

    for filter_obj in filters:
        filter_id = filter_obj.get("id", "(no id)")
        criteria = filter_obj.get("criteria", {})
        action = filter_obj.get("action", {})

        lines.append(f"🔹 Filter ID: {filter_id}")
        lines.append("  Criteria:")

        criteria_lines = []
        if criteria.get("from"):
            criteria_lines.append(f"From: {criteria['from']}")
        if criteria.get("to"):
            criteria_lines.append(f"To: {criteria['to']}")
        if criteria.get("subject"):
            criteria_lines.append(f"Subject: {criteria['subject']}")
        if criteria.get("query"):
            criteria_lines.append(f"Query: {criteria['query']}")
        if criteria.get("negatedQuery"):
            criteria_lines.append(f"Exclude Query: {criteria['negatedQuery']}")
        if criteria.get("hasAttachment"):
            criteria_lines.append("Has attachment")
        if criteria.get("excludeChats"):
            criteria_lines.append("Exclude chats")
        if criteria.get("size"):
            comparison = criteria.get("sizeComparison", "")
            criteria_lines.append(
                f"Size {comparison or ''} {criteria['size']} bytes".strip()
            )

        if not criteria_lines:
            criteria_lines.append("(none)")

        lines.extend([f"    • {line}" for line in criteria_lines])

        lines.append("  Actions:")
        action_lines = []
        if action.get("forward"):
            action_lines.append(f"Forward to: {action['forward']}")
        if action.get("removeLabelIds"):
            action_lines.append(f"Remove labels: {', '.join(action['removeLabelIds'])}")
        if action.get("addLabelIds"):
            action_lines.append(f"Add labels: {', '.join(action['addLabelIds'])}")

        if not action_lines:
            action_lines.append("(none)")

        lines.extend([f"    • {line}" for line in action_lines])
        lines.append("")

    return "\n".join(lines).rstrip()


@server.tool()
@handle_http_errors("create_gmail_filter", service_type="gmail")
@require_google_service("gmail", "gmail_settings_basic")
async def create_gmail_filter(
    service,
    criteria: Dict[str, Any] = Body(
        ..., description="Filter criteria object as defined in the Gmail API."
    ),
    action: Dict[str, Any] = Body(
        ..., description="Filter action object as defined in the Gmail API."
    ),
) -> str:
    """
    Creates a Gmail filter using the users.settings.filters API.

    Args:
        criteria (Dict[str, Any]): Criteria for matching messages.
        action (Dict[str, Any]): Actions to apply to matched messages.

    Returns:
        str: Confirmation message with the created filter ID.
    """
    logger.info("[create_gmail_filter] Invoked")

    filter_body = {"criteria": criteria, "action": action}

    created_filter = await asyncio.to_thread(
        service.users()
        .settings()
        .filters()
        .create(userId="me", body=filter_body)
        .execute
    )

    filter_id = created_filter.get("id", "(unknown)")
    return f"Filter created successfully!\nFilter ID: {filter_id}"


@server.tool()
@handle_http_errors("delete_gmail_filter", service_type="gmail")
@require_google_service("gmail", "gmail_settings_basic")
async def delete_gmail_filter(
    service,
    filter_id: str = Field(..., description="ID of the filter to delete."),
) -> str:
    """
    Deletes a Gmail filter by ID.

    Args:
        filter_id (str): The ID of the filter to delete.

    Returns:
        str: Confirmation message for the deletion.
    """
    logger.info(f"[delete_gmail_filter] Invoked. Filter ID: '{filter_id}'")

    filter_details = await asyncio.to_thread(
        service.users().settings().filters().get(userId="me", id=filter_id).execute
    )

    await asyncio.to_thread(
        service.users().settings().filters().delete(userId="me", id=filter_id).execute
    )

    criteria = filter_details.get("criteria", {})
    action = filter_details.get("action", {})

    return (
        "Filter deleted successfully!\n"
        f"Filter ID: {filter_id}\n"
        f"Criteria: {criteria or '(none)'}\n"
        f"Action: {action or '(none)'}"
    )


@server.tool()
@handle_http_errors("modify_gmail_message_labels", service_type="gmail")
@require_google_service("gmail", GMAIL_MODIFY_SCOPE)
async def modify_gmail_message_labels(
    service,
    message_id: str,
    add_label_ids: List[str] = Field(
        default=[], description="Label IDs to add to the message."
    ),
    remove_label_ids: List[str] = Field(
        default=[], description="Label IDs to remove from the message."
    ),
) -> str:
    """
    Adds or removes labels from a Gmail message.
    To archive an email, remove the INBOX label.
    To delete an email, add the TRASH label.

    Args:
        message_id (str): The ID of the message to modify.
        add_label_ids (Optional[List[str]]): List of label IDs to add to the message.
        remove_label_ids (Optional[List[str]]): List of label IDs to remove from the message.

    Returns:
        str: Confirmation message of the label changes applied to the message.
    """
    logger.info(f"[modify_gmail_message_labels] Invoked. Message ID: '{message_id}'")

    if not add_label_ids and not remove_label_ids:
        raise Exception(
            "At least one of add_label_ids or remove_label_ids must be provided."
        )

    body = {}
    if add_label_ids:
        body["addLabelIds"] = add_label_ids
    if remove_label_ids:
        body["removeLabelIds"] = remove_label_ids

    await asyncio.to_thread(
        service.users().messages().modify(userId="me", id=message_id, body=body).execute
    )

    actions = []
    if add_label_ids:
        actions.append(f"Added labels: {', '.join(add_label_ids)}")
    if remove_label_ids:
        actions.append(f"Removed labels: {', '.join(remove_label_ids)}")

    return f"Message labels updated successfully!\nMessage ID: {message_id}\n{'; '.join(actions)}"


@server.tool()
@handle_http_errors("batch_modify_gmail_message_labels", service_type="gmail")
@require_google_service("gmail", GMAIL_MODIFY_SCOPE)
async def batch_modify_gmail_message_labels(
    service,
    message_ids: List[str],
    add_label_ids: List[str] = Field(
        default=[], description="Label IDs to add to messages."
    ),
    remove_label_ids: List[str] = Field(
        default=[], description="Label IDs to remove from messages."
    ),
) -> str:
    """
    Adds or removes labels from multiple Gmail messages in a single batch request.

    Args:
        message_ids (List[str]): A list of message IDs to modify.
        add_label_ids (Optional[List[str]]): List of label IDs to add to the messages.
        remove_label_ids (Optional[List[str]]): List of label IDs to remove from the messages.

    Returns:
        str: Confirmation message of the label changes applied to the messages.
    """
    logger.info(
        f"[batch_modify_gmail_message_labels] Invoked. Message IDs: '{message_ids}'"
    )

    if not add_label_ids and not remove_label_ids:
        raise Exception(
            "At least one of add_label_ids or remove_label_ids must be provided."
        )

    body = {"ids": message_ids}
    if add_label_ids:
        body["addLabelIds"] = add_label_ids
    if remove_label_ids:
        body["removeLabelIds"] = remove_label_ids

    await asyncio.to_thread(
        service.users().messages().batchModify(userId="me", body=body).execute
    )

    actions = []
    if add_label_ids:
        actions.append(f"Added labels: {', '.join(add_label_ids)}")
    if remove_label_ids:
        actions.append(f"Removed labels: {', '.join(remove_label_ids)}")

    return f"Labels updated for {len(message_ids)} messages: {'; '.join(actions)}"


# ── MCP Resource Templates ──────────────────────────────────────────────


@server.resource(
    "gmail://messages/{message_id}/attachments/{attachment_id}",
    name="gmail_attachment",
    description="Raw attachment content from a Gmail message, returned as base64-encoded bytes.",
    mime_type="application/octet-stream",
)
@require_google_service("gmail", "gmail_read")
async def gmail_attachment_resource(
    service,
    message_id: str,
    attachment_id: str,
) -> bytes:
    """Fetch raw attachment bytes from a Gmail message."""
    attachment = await asyncio.to_thread(
        service.users()
        .messages()
        .attachments()
        .get(userId="me", messageId=message_id, id=attachment_id)
        .execute
    )
    base64_data = attachment.get("data", "")
    return base64.urlsafe_b64decode(base64_data)