team-tryouts/app/discord_bot.py

"""Unified Discord bot for Team Tryouts notifications.

This module provides a persistent bot that handles:
- One on One request approvals/rejections via reactions
- Match/tryout schedule addition notifications with attendance confirmation
- Daily reminders at 18:00 EDT for upcoming events
"""

import os
import json
import logging
import tempfile
import time
import asyncio
import threading
import traceback
from datetime import datetime, timedelta
from zoneinfo import ZoneInfo
from queue import Queue, Empty
from discord import Intents
from discord.ext import commands
from apscheduler.schedulers.asyncio import AsyncIOScheduler
from apscheduler.triggers.cron import CronTrigger
from dotenv import load_dotenv

load_dotenv()
DISCORD_BOT_TOKEN = os.getenv('DISCORD_BOT_TOKEN')

# Configure logging
logger = logging.getLogger(__name__)

# File for persisting pending requests across bot restarts
PENDING_FILE = os.path.join(
    os.path.dirname(os.path.dirname(os.path.abspath(__file__))), 'discord_pending.json'
)

# Emoji constants
#: Entries older than this are dropped when the file is loaded: a message
#: nobody reacted to in a month will not be reacted to (OPS-007).
PENDING_MAX_AGE_DAYS = 30

#: How late the daily reminder may still be sent. Long enough to survive a
#: restart or a slow start-up, short of the next day's occurrence.
REMINDER_GRACE_SECONDS = 3600

CHECK_EMOJI = '✅'  # Green checkmark
CROSS_EMOJI = '❌'  # Red X


class TeamTryoutsBot(commands.Bot):
    """Unified Discord bot for Team Tryouts notifications.

    Handles One on One requests, schedule additions, and daily reminders.
    """

    def __init__(self, flask_app=None):
        # Only what the bot actually reads. `members` — the privileged
        # GUILD_MEMBERS intent — was requested and never used: nothing here
        # lists or looks up guild members, the bot reaches people through
        # the discord_user_id stored on their account (OPS-014).
        #
        # `message_content` stays: on_raw_reaction_add reads the text of a
        # coach's reply to record a refusal note.
        intents = Intents.default()
        intents.message_content = True
        intents.dm_messages = True
        intents.dm_reactions = True
        intents.reactions = True
        intents.guilds = True

        super().__init__(command_prefix='!', intents=intents)
        self.flask_app = flask_app
        self.pending_requests = {}  # Maps message_id to {type, id} for reaction handling
        self.message_queue = Queue()  # Thread-safe queue for messages from Flask
        self.scheduler = AsyncIOScheduler()
        self.timezone = ZoneInfo('America/Toronto')  # EDT timezone

    def _load_pending(self):
        """Load pending requests from the JSON file.

        A corrupt file used to be logged at error level and then silently
        replaced by an empty dict: every in-flight Discord reaction stopped
        having any effect, and nothing said so (OPS-006). The file is now
        moved aside instead of overwritten, so the mapping can be recovered
        by hand, and the message says what was lost.

        Entries older than PENDING_MAX_AGE_DAYS are dropped here rather
        than kept forever (OPS-007). A message nobody reacted to in a month
        is not going to be reacted to.
        """
        if not os.path.exists(PENDING_FILE):
            logger.info('No pending requests file found, starting fresh.')
            return

        try:
            with open(PENDING_FILE, encoding='utf-8') as handle:
                data = json.load(handle)
            if not isinstance(data, dict):
                raise ValueError(f'expected an object, found {type(data).__name__}')
            # Keys are Discord message ids; JSON turns them into strings.
            loaded = {int(key): value for key, value in data.items()}
        except (OSError, ValueError) as exc:
            quarantine = f'{PENDING_FILE}.corrupt-{int(time.time())}'
            try:
                os.replace(PENDING_FILE, quarantine)
            except OSError:
                quarantine = '(could not be moved aside)'
            logger.error(
                'Pending requests file unreadable (%s). Moved to %s. Reactions on '
                'messages already sent will no longer be recognised until those '
                'requests are answered in the web interface.',
                exc,
                quarantine,
            )
            return

        kept, expired = self._drop_expired(loaded)
        self.pending_requests = kept
        logger.info(
            'Loaded %d pending requests from %s (%d expired and dropped)',
            len(kept),
            PENDING_FILE,
            expired,
        )
        if expired:
            self._save_pending()

    @staticmethod
    def _drop_expired(entries):
        """Split loaded entries into the ones still worth keeping.

        Args:
            entries: message_id → record.

        Returns:
            tuple[dict, int]: Entries to keep, and how many were dropped.
            A record without a timestamp predates this field and is kept —
            dropping it would be guessing.
        """
        cutoff = time.time() - PENDING_MAX_AGE_DAYS * 86400
        kept = {}
        expired = 0
        for message_id, record in entries.items():
            created = record.get('created_at') if isinstance(record, dict) else None
            if created is not None and created < cutoff:
                expired += 1
                continue
            kept[message_id] = record
        return kept, expired

    def _save_pending(self):
        """Write the pending requests to disk, atomically.

        The previous version opened the destination for writing and then
        serialised into it: an interruption anywhere in between left a
        truncated JSON file, which the loader could not read. Writing to a
        neighbouring temporary file and renaming means the destination is
        either the old content or the new one, never half of either.
        """
        directory = os.path.dirname(PENDING_FILE) or '.'
        try:
            with tempfile.NamedTemporaryFile(
                'w', encoding='utf-8', dir=directory, prefix='.pending-', delete=False
            ) as handle:
                json.dump(self.pending_requests, handle, indent=2)
                handle.flush()
                os.fsync(handle.fileno())
                temporary = handle.name
            os.replace(temporary, PENDING_FILE)
        except OSError as exc:
            logger.error('Could not save pending requests: %s', exc)

    async def setup_hook(self):
        """Called when the bot is ready."""
        self._load_pending()
        logger.info(f'TeamTryoutsBot logged in as {self.user}')

    async def on_ready(self):
        """Log when the bot is ready and start background tasks."""
        try:
            guilds = [g.name for g in self.guilds]
            logger.info(f'TeamTryoutsBot is ready! Logged in as {self.user} | Guilds: {guilds}')
        except Exception:
            logger.info(f'TeamTryoutsBot is ready! Logged in as {self.user}')

        # Start the queue processing task
        self.loop.create_task(self.process_queue())

        # Start the daily reminder scheduler
        self.loop.create_task(self.start_scheduler())

    async def start_scheduler(self):
        """Start the APScheduler for daily reminders.

        `coalesce` and `misfire_grace_time` are the two settings this job
        needs and did not have (OPS-005). Without a grace time, a restart at
        18:05 dropped the day's reminders with no trace; without coalescing,
        a scheduler that wakes up behind schedule fires once per missed run,
        so players receive the same reminder several times.

        The grace period is deliberately short of the next occurrence: a
        reminder for tonight is worth sending an hour late, not tomorrow.
        """
        try:
            self.scheduler.add_job(
                self.send_daily_reminders,
                trigger=CronTrigger(hour=18, minute=0, timezone=self.timezone),
                id='daily_reminders',
                replace_existing=True,
                coalesce=True,
                misfire_grace_time=REMINDER_GRACE_SECONDS,
                max_instances=1,
            )
            self.scheduler.start()
            logger.info('Daily reminder scheduler started (18:00 EDT)')
        except Exception as e:
            logger.error(f'Error starting scheduler: {e}')

    async def process_queue(self):
        """Process messages from the queue (runs continuously)."""
        while True:
            try:
                try:
                    item = self.message_queue.get_nowait()
                except Empty:
                    await asyncio.sleep(0.5)
                    continue

                if item.get('type') == 'one_on_one_request':
                    await self._send_one_on_one_dm(**item['data'])
                elif item.get('type') == 'schedule_addition':
                    if self.flask_app:
                        with self.flask_app.app_context():
                            await self._send_schedule_notification(**item['data'])
                    else:
                        await self._send_schedule_notification(**item['data'])
                elif item.get('type') == 'one_on_one_response':
                    await self._send_one_on_one_response_dm(**item['data'])

            except Exception as e:
                logger.error(f"Error processing queue: {e}\n{traceback.format_exc()}")
            await asyncio.sleep(0.1)

    def is_dm_channel(self, channel) -> bool:
        """Check if a channel is a DM channel."""
        return hasattr(channel, 'recipient') or hasattr(channel, 'recipients')

    async def on_raw_reaction_add(self, payload):
        """Handle when a reaction is added to a message (works even after bot restart)."""
        # Ignore bot's own reactions
        if payload.user_id == self.user.id:
            return

        # Check if this is a pending request we're tracking
        if payload.message_id not in self.pending_requests:
            return

        # Fetch the channel and check if it's a DM
        try:
            channel = await self.fetch_channel(payload.channel_id)
        except Exception:
            return

        if not self.is_dm_channel(channel):
            return

        # Fetch the user who reacted
        try:
            user = await self.fetch_user(payload.user_id)
        except Exception:
            return

        if user is None:
            return

        request_info = self.pending_requests[payload.message_id]
        emoji_str = str(payload.emoji)

        handler_type = request_info.get('type')
        request_id = request_info.get('id')

        if emoji_str == CHECK_EMOJI:
            if handler_type == 'one_on_one':
                if self.flask_app:
                    with self.flask_app.app_context():
                        await self.handle_one_on_one_approve(
                            user, payload.message_id, request_id, channel
                        )
                else:
                    await self.handle_one_on_one_approve(
                        user, payload.message_id, request_id, channel
                    )
            elif handler_type == 'schedule_addition':
                if self.flask_app:
                    with self.flask_app.app_context():
                        await self.handle_attendance_confirm(
                            user, payload.message_id, request_id, channel
                        )
                else:
                    await self.handle_attendance_confirm(
                        user, payload.message_id, request_id, channel
                    )
        elif emoji_str == CROSS_EMOJI:
            if handler_type == 'one_on_one':
                if self.flask_app:
                    with self.flask_app.app_context():
                        await self.handle_one_on_one_reject(
                            user, payload.message_id, request_id, channel
                        )
                else:
                    await self.handle_one_on_one_reject(
                        user, payload.message_id, request_id, channel
                    )
            elif handler_type == 'schedule_addition':
                if self.flask_app:
                    with self.flask_app.app_context():
                        await self.handle_attendance_decline(
                            user, payload.message_id, request_id, channel
                        )
                else:
                    await self.handle_attendance_decline(
                        user, payload.message_id, request_id, channel
                    )

    async def _send_one_on_one_dm(
        self,
        coach_name: str,
        coach_discord_id: str,
        player_name: str,
        team_name: str,
        date_str: str,
        start_time: str,
        end_time: str,
        points: str,
        request_id: int,
    ) -> int:
        """Send a One on One request DM to a coach with reactions."""
        try:
            user_id = int(coach_discord_id)
        except (ValueError, TypeError):
            logger.warning(f"Invalid coach_discord_id '{coach_discord_id}'")
            return None

        try:
            user = await self.fetch_user(user_id)
            if not user:
                return None

            message = (
                "📅 **One on One Request**\n\n"
                f"**Player:** {player_name}\n"
                f"**Team:** {team_name or 'Unknown Team'}\n"
                f"**Date:** {date_str}\n"
                f"**Time:** {start_time} - {end_time}\n"
                f"**Discussion Points:** {points or 'No specific points provided'}\n\n"
                "Please respond by clicking a reaction below:\n"
                f"{CHECK_EMOJI} - Confirm the meeting\n"
                f"{CROSS_EMOJI} - Decline (you can add a reason by replying before clicking)"
            )

            msg = await user.send(message)
            await msg.add_reaction(CHECK_EMOJI)
            await msg.add_reaction(CROSS_EMOJI)

            # Track this pending request
            self.pending_requests[msg.id] = {
                'type': 'one_on_one',
                'id': request_id,
                'created_at': time.time(),
            }
            self._save_pending()

            logger.info(f"Sent One on One DM with reactions, message_id={msg.id}")
            return msg.id

        except Exception as e:
            logger.error(f"Error sending One on One DM: {e}")
        return None

    async def _send_schedule_notification(
        self,
        user_id: int,
        event_type: str,
        event_title: str,
        event_date: str,
        event_time: str,
        reference_id: int,
    ) -> int:
        """Send a schedule addition notification to a player.

        Args:
            user_id: Database primary key of the User (NOT Discord user ID).
            event_type: 'match' or 'tryout'.
            event_title: Title of the event.
            event_date: Date string.
            event_time: Time string.
            reference_id: ID of the MatchParticipant or TryoutRegistration record.
        """
        try:
            # Look up the DB user to get their Discord user ID
            from app.models import User as DBUser

            db_user = DBUser.query.get(user_id)
            if not db_user:
                logger.warning(f"DB user {user_id} not found for schedule notification")
                return None

            if not db_user.discord_user_id:
                logger.warning(f"User {db_user.username} has no Discord user ID, cannot send DM")
                return None

            discord_uid = int(db_user.discord_user_id)
            user = await self.fetch_user(discord_uid)
            if not user:
                logger.warning(f"Could not fetch Discord user {discord_uid}")
                return None

            event_name = "Match" if event_type == 'match' else "Tryout"

            message = (
                f"📅 **{event_name} Scheduled**\n\n"
                f"You have been added to the following {event_type}:\n"
                f"**{event_title}**\n"
                f"**Date:** {event_date}\n"
                f"**Time:** {event_time}\n\n"
                "Please confirm your attendance:\n"
                f"{CHECK_EMOJI} - Confirm attendance\n"
                f"{CROSS_EMOJI} - Decline"
            )

            msg = await user.send(message)
            await msg.add_reaction(CHECK_EMOJI)
            await msg.add_reaction(CROSS_EMOJI)

            # Track this pending request
            self.pending_requests[msg.id] = {
                'type': 'schedule_addition',
                'id': reference_id,
                'event_type': event_type,
                'created_at': time.time(),
            }
            self._save_pending()

            logger.info(
                f"Sent {event_type} schedule notification to {db_user.username}, message_id={msg.id}"
            )
            return msg.id

        except Exception as e:
            logger.error(f"Error sending schedule notification: {e}")
        return None

    async def handle_one_on_one_approve(self, coach, message_id, request_id, channel):
        """Handle coach approving a One on One request."""
        try:
            from app.models import OneOnOneRequest
            from app.extensions import db

            request = OneOnOneRequest.query.get(request_id)
            if not request:
                return

            if request.coach.discord_user_id != str(coach.id):
                await channel.send("⚠️ You are not the intended recipient.")
                return

            # Re-attach to current session (object may be detached across app contexts)
            request = db.session.merge(request)

            # Capture data before commit
            player_full_name = request.player.full_name if request.player else 'Unknown'
            player_discord_id = request.player.discord_user_id if request.player else None
            coach_obj = request.coach

            request.status = 'approved'
            request.responded_at = datetime.utcnow()
            db.session.commit()

            await channel.send(
                f"✅ You have **approved** the One on One session with {player_full_name}."
            )

            # Notify player via Discord
            if player_discord_id:
                await self.notify_player_about_one_on_one_direct(
                    player_discord_id=player_discord_id,
                    player_full_name=player_full_name,
                    coach_full_name=coach_obj.full_name if coach_obj else 'Coach',
                    request=request,
                    approved=True,
                )
            del self.pending_requests[message_id]
            self._save_pending()

        except Exception as e:
            logger.error(f"Error handling approval: {e}\n{traceback.format_exc()}")

    async def handle_one_on_one_reject(self, coach, message_id, request_id, channel):
        """Handle coach rejecting a One on One request."""
        try:
            from app.models import OneOnOneRequest
            from app.extensions import db

            request = OneOnOneRequest.query.get(request_id)
            if not request:
                return

            if request.coach.discord_user_id != str(coach.id):
                await channel.send("⚠️ You are not the intended recipient.")
                return

            # Re-attach to current session (object may be detached across app contexts)
            request = db.session.merge(request)

            player_full_name = request.player.full_name if request.player else 'Unknown'
            player_discord_id = request.player.discord_user_id if request.player else None
            coach_obj = request.coach

            refusal_note = None
            try:
                async for reply in channel.history(limit=20):
                    if (
                        reply.author.id == coach.id
                        and reply.reference
                        and reply.reference.message_id == message_id
                    ):
                        refusal_note = reply.content
                        break
            except Exception as e:
                logger.warning(f"Could not check for reply message: {e}")

            request.status = 'rejected'
            request.responded_at = datetime.utcnow()
            if refusal_note:
                request.coach_rejection_message = refusal_note
            db.session.commit()

            rejection_msg = (
                f"❌ You have **rejected** the One on One session with {player_full_name}."
            )
            if refusal_note:
                rejection_msg += f"\n**Reason:** {refusal_note}"
            else:
                rejection_msg += "\n\nℹ️ The player has been notified that you are not available."

            await channel.send(rejection_msg)
            if player_discord_id:
                await self.notify_player_about_one_on_one_direct(
                    player_discord_id=player_discord_id,
                    player_full_name=player_full_name,
                    coach_full_name=coach_obj.full_name if coach_obj else 'Coach',
                    request=request,
                    approved=False,
                    refusal_note=refusal_note,
                )
            del self.pending_requests[message_id]
            self._save_pending()

        except Exception as e:
            logger.error(f"Error handling rejection: {e}\n{traceback.format_exc()}")

    @staticmethod
    def _attendance_record(event_type, reference_id):
        """The row an attendance reaction refers to, and whose it is.

        Args:
            event_type: 'match' or 'tryout'.
            reference_id: Primary key of the participation row.

        Returns:
            tuple: (row, player_id) — either may be None.
        """
        from app.models import MatchParticipant, TryoutRegistration

        if event_type == 'match':
            row = MatchParticipant.query.get(reference_id)
        elif event_type == 'tryout':
            row = TryoutRegistration.query.get(reference_id)
        else:
            row = None
        return row, getattr(row, 'player_id', None)

    @staticmethod
    def _reacting_user_owns(player_id, reacting_user):
        """Whether the Discord account that reacted is the row's owner.

        handle_one_on_one_approve and _reject have always compared the
        reacting account against the coach the request was sent to. The two
        attendance handlers did not (OPS-009) — same message shape, same
        threat, one of them checked. The asymmetry was the bug.
        """
        from app.models import User

        if not player_id:
            return False
        owner = User.query.get(player_id)
        return bool(owner and owner.discord_user_id == str(reacting_user.id))

    async def handle_attendance_confirm(self, player, message_id, reference_id, channel):
        """Handle player confirming attendance for a match/tryout."""
        try:
            from app.extensions import db

            request_info = self.pending_requests[message_id]
            event_type = request_info.get('event_type')
            row, player_id = self._attendance_record(event_type, reference_id)

            if row is not None and not self._reacting_user_owns(player_id, player):
                await channel.send("⚠️ You are not the intended recipient.")
                return

            if row is not None:
                row = db.session.merge(row)
                if event_type == 'match':
                    row.attendance_confirmed = True
                else:
                    # TryoutRegistration has no attendance_confirmed column
                    # (DB-008, waiting on Alembic). Assigning here sets a
                    # Python attribute that is never written, so the player
                    # was told "confirmed" and nothing was recorded. Still
                    # true — but no longer silent.
                    logger.warning(
                        'Tryout attendance confirmation from user_id=%s for '
                        'registration %s was not persisted: TryoutRegistration '
                        'has no attendance_confirmed column (DB-008).',
                        player.id,
                        reference_id,
                    )

            db.session.commit()

            await channel.send("✅ Your attendance has been confirmed!")
            del self.pending_requests[message_id]
            self._save_pending()

        except Exception as e:
            logger.error(f"Error handling attendance confirmation: {e}\n{traceback.format_exc()}")

    async def handle_attendance_decline(self, player, message_id, reference_id, channel):
        """Handle player declining attendance for a match/tryout."""
        try:
            from app.extensions import db

            request_info = self.pending_requests[message_id]
            event_type = request_info.get('event_type')
            row, player_id = self._attendance_record(event_type, reference_id)

            if row is not None and not self._reacting_user_owns(player_id, player):
                await channel.send("⚠️ You are not the intended recipient.")
                return

            if row is not None:
                row = db.session.merge(row)
                if event_type == 'match':
                    db.session.delete(row)
                else:
                    row.status = 'no_show'

            db.session.commit()

            await channel.send("❌ Your attendance has been declined.")
            del self.pending_requests[message_id]
            self._save_pending()

        except Exception as e:
            logger.error(f"Error handling attendance decline: {e}\n{traceback.format_exc()}")

    async def notify_player_about_one_on_one_direct(
        self,
        player_discord_id,
        player_full_name,
        coach_full_name,
        request,
        approved=True,
        refusal_note=None,
    ):
        """Send confirmation to player about One on One response using pre-fetched data.

        This method avoids session expiration issues by using data captured before
        the database commit.

        Args:
            player_discord_id: The player's Discord user ID string.
            player_full_name: The player's full name.
            coach_full_name: The coach's full name.
            request: The OneOnOneRequest object (for date/time/points data only).
            approved: Whether the session was approved.
            refusal_note: Optional coach refusal reason.
        """
        try:
            if not player_discord_id:
                logger.warning(f"Player has no Discord user ID for request {request.id}")
                return

            player_user = await self.fetch_user(int(player_discord_id))
            if not player_user:
                logger.warning(f"Could not fetch Discord user {player_discord_id}")
                return

            if approved:
                message = (
                    "🎉 **One on One Session Confirmed!**\n\n"
                    f"Your coach **{coach_full_name}** has approved your request:\n"
                    f"**Date:** {request.date.strftime('%A, %B %d, %Y')}\n"
                    f"**Time:** {request.start_time.strftime('%I:%M %p')} - {request.end_time.strftime('%I:%M %p')}\n"
                    f"**Discussion Points:** {request.points or 'No specific points provided'}\n\n"
                    "Please prepare for your session!"
                )
            else:
                if refusal_note:
                    message = (
                        "😞 **One on One Session Rejected**\n\n"
                        f"Your coach **{coach_full_name}** has declined:\n"
                        f"**Reason:** {refusal_note}\n\n"
                        "Please try selecting a different time slot."
                    )
                else:
                    message = (
                        "😞 **One on One Session Unavailable**\n\n"
                        f"Your coach **{coach_full_name}** is not available.\n\n"
                        "Please try selecting a different time slot."
                    )

            await player_user.send(message)
            logger.info(
                f"Sent One on One notification to player {player_full_name} (request {request.id})"
            )

        except Exception as e:
            logger.error(f"Error in direct One on One notification: {e}")

    async def send_daily_reminders(self):
        """Send daily reminders at 18:00 EDT for events in 24-48 hours."""
        try:
            if self.flask_app:
                with self.flask_app.app_context():
                    await self._send_daily_reminders_impl()
            else:
                await self._send_daily_reminders_impl()
        except Exception as e:
            logger.error(f"Error sending daily reminders: {e}\n{traceback.format_exc()}")

    async def _send_daily_reminders_impl(self):
        """Internal implementation of daily reminders with proper app context."""
        try:
            from app.models import (
                Match,
                Tryout,
                MatchParticipant,
                TryoutRegistration,
                OneOnOneRequest,
            )
            from sqlalchemy.orm import joinedload

            now = datetime.now(self.timezone)
            tomorrow = now.date() + timedelta(days=1)

            # Find matches for tomorrow
            matches = Match.query.filter(Match.date == tomorrow).all()
            for match in matches:
                participants = MatchParticipant.query.filter_by(match_id=match.id).all()
                for participant in participants:
                    if participant.player.discord_user_id:
                        await self.send_match_reminder(participant.player, match)

            # Find tryouts for tomorrow
            tryouts = Tryout.query.filter(Tryout.date == tomorrow).all()
            for tryout in tryouts:
                registrations = TryoutRegistration.query.filter_by(tryout_id=tryout.id).all()
                for reg in registrations:
                    if reg.player.discord_user_id:
                        await self.send_tryout_reminder(reg.player, tryout)

            # Find One on One sessions for tomorrow (only approved ones)
            one_on_ones = (
                OneOnOneRequest.query.options(
                    joinedload(OneOnOneRequest.player), joinedload(OneOnOneRequest.coach)
                )
                .filter(OneOnOneRequest.date == tomorrow, OneOnOneRequest.status == 'approved')
                .all()
            )
            for session in one_on_ones:
                if session.player and session.player.discord_user_id:
                    await self.send_one_on_one_reminder(session.player, session)

        except Exception as e:
            logger.error(f"Error sending daily reminders: {e}")

    async def send_match_reminder(self, player, match):
        """Send match reminder to player."""
        try:
            player_user = await self.fetch_user(int(player.discord_user_id))
            message = (
                "🔔 **Match Reminder**\n\n"
                f"Your match **{match.title}** is scheduled for tomorrow:\n"
                f"**Date:** {match.date.strftime('%A, %B %d, %Y')}\n"
                f"**Time:** {match.start_time.strftime('%I:%M %p') if match.start_time else 'TBD'} - "
                f"{match.end_time.strftime('%I:%M %p') if match.end_time else 'TBD'}\n"
                f"**Location:** {match.location or 'TBD'}\n\n"
                "Please confirm your attendance in the app."
            )
            await player_user.send(message)
        except Exception as e:
            logger.error(f"Error sending match reminder: {e}")

    async def send_tryout_reminder(self, player, tryout):
        """Send tryout reminder to player."""
        try:
            player_user = await self.fetch_user(int(player.discord_user_id))
            message = (
                "🔔 **Tryout Reminder**\n\n"
                f"Your tryout **{tryout.title}** is scheduled for tomorrow:\n"
                f"**Date:** {tryout.date.strftime('%A, %B %d, %Y')}\n"
                f"**Location:** {tryout.location or 'TBD'}\n\n"
                "Please confirm your attendance in the app."
            )
            await player_user.send(message)
        except Exception as e:
            logger.error(f"Error sending tryout reminder: {e}")

    async def _send_one_on_one_response_dm(
        self,
        player_discord_id: str,
        player_full_name: str,
        coach_full_name: str,
        date_str: str,
        start_time: str,
        end_time: str,
        points: str,
        approved: bool,
        refusal_note: str = None,
    ) -> bool:
        """Send a DM to a player notifying them of their One on One request response.

        Called from the message queue when a coach accepts/rejects via the web app.
        """
        try:
            if not player_discord_id:
                logger.warning("Cannot send response DM: no player_discord_id")
                return False

            player_user = await self.fetch_user(int(player_discord_id))
            if not player_user:
                logger.warning(f"Could not fetch Discord user {player_discord_id}")
                return False

            if approved:
                message = (
                    "🎉 **One on One Session Confirmed!**\n\n"
                    f"Your coach **{coach_full_name}** has approved your request:\n"
                    f"**Date:** {date_str}\n"
                    f"**Time:** {start_time} - {end_time}\n"
                    f"**Discussion Points:** {points or 'No specific points provided'}\n\n"
                    "Please prepare for your session!"
                )
            else:
                if refusal_note:
                    message = (
                        "😞 **One on One Session Rejected**\n\n"
                        f"Your coach **{coach_full_name}** has declined:\n"
                        f"**Reason:** {refusal_note}\n\n"
                        "Please try selecting a different time slot."
                    )
                else:
                    message = (
                        "😞 **One on One Session Unavailable**\n\n"
                        f"Your coach **{coach_full_name}** is not available.\n\n"
                        "Please try selecting a different time slot."
                    )

            await player_user.send(message)
            logger.info(
                f"Sent One on One response DM to player {player_full_name} (approved={approved})"
            )
            return True

        except Exception as e:
            logger.error(f"Error sending One on One response DM: {e}")
            return False

    async def send_one_on_one_reminder(self, player, session):
        """Send One on One reminder to player."""
        try:
            player_user = await self.fetch_user(int(player.discord_user_id))
            message = (
                "🔔 **One on One Reminder**\n\n"
                f"Your One on One session with **{session.coach.full_name}** is scheduled for tomorrow:\n"
                f"**Date:** {session.date.strftime('%A, %B %d, %Y')}\n"
                f"**Time:** {session.start_time.strftime('%I:%M %p')} - {session.end_time.strftime('%I:%M %p')}\n"
                f"**Discussion Points:** {session.points or 'No specific points provided'}\n\n"
                "Please prepare for your session!"
            )
            await player_user.send(message)
        except Exception as e:
            logger.error(f"Error sending One on One reminder: {e}")


# Global bot instance
bot_instance = None
bot_thread = None


def get_bot(flask_app=None):
    """Get or create the bot instance."""
    global bot_instance
    if bot_instance is None:
        bot_instance = TeamTryoutsBot(flask_app=flask_app)
    elif flask_app is not None and bot_instance.flask_app is None:
        bot_instance.flask_app = flask_app
    return bot_instance


def send_one_on_one_dm(
    coach_name: str,
    coach_discord_id: str,
    player_name: str,
    team_name: str,
    date_str: str,
    start_time: str,
    end_time: str,
    points: str,
    request_id: int,
) -> bool:
    """Queue a One on One request DM to be sent by the bot."""
    bot = get_bot()
    try:
        bot.message_queue.put(
            {
                'type': 'one_on_one_request',
                'data': {
                    'coach_name': coach_name,
                    'coach_discord_id': coach_discord_id,
                    'player_name': player_name,
                    'team_name': team_name,
                    'date_str': date_str,
                    'start_time': start_time,
                    'end_time': end_time,
                    'points': points,
                    'request_id': request_id,
                },
            }
        )
        return True
    except Exception as e:
        logger.error(f"Error queuing One on One DM: {e}")
        return False


def send_schedule_notification(
    user_id: int,
    event_type: str,
    event_title: str,
    event_date: str,
    event_time: str,
    reference_id: int,
) -> bool:
    """Queue a schedule addition notification to be sent by the bot."""
    bot = get_bot()
    try:
        bot.message_queue.put(
            {
                'type': 'schedule_addition',
                'data': {
                    'user_id': user_id,
                    'event_type': event_type,
                    'event_title': event_title,
                    'event_date': event_date,
                    'event_time': event_time,
                    'reference_id': reference_id,
                },
            }
        )
        return True
    except Exception as e:
        logger.error(f"Error queuing schedule notification: {e}")
        return False


def send_one_on_one_response(
    player_discord_id: str,
    player_full_name: str,
    coach_full_name: str,
    date_str: str,
    start_time: str,
    end_time: str,
    points: str,
    approved: bool,
    refusal_note: str = None,
) -> bool:
    """Queue a One on One response DM to be sent to the player by the bot.

    Called from Flask routes when a coach accepts/rejects via the web app.
    """
    bot = get_bot()
    try:
        bot.message_queue.put(
            {
                'type': 'one_on_one_response',
                'data': {
                    'player_discord_id': player_discord_id,
                    'player_full_name': player_full_name,
                    'coach_full_name': coach_full_name,
                    'date_str': date_str,
                    'start_time': start_time,
                    'end_time': end_time,
                    'points': points,
                    'approved': approved,
                    'refusal_note': refusal_note,
                },
            }
        )
        return True
    except Exception as e:
        logger.error(f"Error queuing One on One response DM: {e}")
        return False


def start_bot(flask_app=None):
    """Start the Discord bot in the background."""
    global bot_thread

    bot = get_bot(flask_app=flask_app)
    if DISCORD_BOT_TOKEN and bot_thread is None:

        def run_bot():
            try:
                bot.run(DISCORD_BOT_TOKEN)
            except Exception as e:
                logger.error(f"Bot error: {e}")
            finally:
                # bot.run() returning means the connection is gone for good:
                # discord.py reconnects on its own for anything recoverable.
                # Recording it is what makes bot_status() able to say 'stopped'
                # instead of reporting a dead thread as running.
                logger.error('Discord bot loop exited; notifications are no longer being sent')

        bot_thread = threading.Thread(target=run_bot, daemon=True)
        bot_thread.start()
        logger.info("TeamTryoutsBot started in background thread")
    elif not DISCORD_BOT_TOKEN:
        logger.warning("DISCORD_BOT_TOKEN not set, bot not started")


def bot_status():
    """What the bot is doing, for /health (OPS-012).

    The bot runs in a daemon thread inside the web process. When that
    thread dies — a revoked token, a fatal gateway error — the web
    application keeps serving pages and no notification is ever sent again.
    Nothing reported it, so nobody found out until someone asked why they
    had stopped receiving reminders.

    Returns:
        dict: `configured` (a token is set), `running` (the thread is
        alive), `connected` (the gateway session is up) and `pending`
        (reaction mappings held in memory).
    """
    running = bool(bot_thread and bot_thread.is_alive())
    instance = bot_instance
    connected = bool(instance and not instance.is_closed() and instance.is_ready())
    return {
        'configured': bool(DISCORD_BOT_TOKEN),
        'running': running,
        'connected': connected,
        'pending': len(instance.pending_requests) if instance else 0,
    }