mautrix-instagram/mautrix_instagram/portal.py

# mautrix-instagram - A Matrix-Instagram puppeting bridge.
# Copyright (C) 2022 Tulir Asokan
#
# This program is free software: you can redistribute it and/or modify
# it under the terms of the GNU Affero General Public License as published by
# the Free Software Foundation, either version 3 of the License, or
# (at your option) any later version.
#
# This program is distributed in the hope that it will be useful,
# but WITHOUT ANY WARRANTY; without even the implied warranty of
# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
# GNU Affero General Public License for more details.
#
# You should have received a copy of the GNU Affero General Public License
# along with this program.  If not, see <https://www.gnu.org/licenses/>.
from __future__ import annotations

from typing import TYPE_CHECKING, Any, AsyncGenerator, Awaitable, Callable, Union, cast
from collections import deque
from io import BytesIO
import asyncio
import json
import mimetypes
import re
import sqlite3
import time

import asyncpg
import magic

from mauigpapi.types import (
    AnimatedMediaItem,
    CommandResponse,
    ExpiredMediaItem,
    MediaShareItem,
    MediaType,
    MessageSyncMessage,
    Reaction,
    ReactionStatus,
    ReelMediaShareItem,
    ReelShareType,
    RegularMediaItem,
    Thread,
    ThreadItem,
    ThreadItemType,
    ThreadUser,
    ThreadUserLastSeenAt,
    TypingStatus,
    VoiceMediaItem,
)
from mautrix.appservice import AppService, IntentAPI
from mautrix.bridge import BasePortal, NotificationDisabler, async_getter_lock
from mautrix.errors import MatrixError, MForbidden, MNotFound, SessionNotFound
from mautrix.types import (
    AudioInfo,
    BeeperMessageStatusEventContent,
    ContentURI,
    EventID,
    EventType,
    Format,
    ImageInfo,
    LocationMessageEventContent,
    MediaMessageEventContent,
    MessageEventContent,
    MessageStatus,
    MessageStatusReason,
    MessageType,
    RelatesTo,
    RelationType,
    RoomID,
    TextMessageEventContent,
    UserID,
    VideoInfo,
)
from mautrix.util import ffmpeg
from mautrix.util.message_send_checkpoint import MessageSendCheckpointStatus
from mautrix.util.simple_lock import SimpleLock

from . import matrix as m, puppet as p, user as u
from .config import Config
from .db import Message as DBMessage, Portal as DBPortal, Reaction as DBReaction

if TYPE_CHECKING:
    from .__main__ import InstagramBridge

try:
    from mautrix.crypto.attachments import decrypt_attachment, encrypt_attachment
except ImportError:
    encrypt_attachment = decrypt_attachment = None

try:
    from PIL import Image
except ImportError:
    Image = None


StateBridge = EventType.find("m.bridge", EventType.Class.STATE)
StateHalfShotBridge = EventType.find("uk.half-shot.bridge", EventType.Class.STATE)
MediaData = Union[
    AnimatedMediaItem,
    ExpiredMediaItem,
    MediaShareItem,
    ReelMediaShareItem,
    RegularMediaItem,
    VoiceMediaItem,
]
MediaUploadFunc = Callable[["u.User", MediaData, IntentAPI], Awaitable[MediaMessageEventContent]]

# This doesn't need to capture all valid URLs, it's enough to catch most of them.
# False negatives simply mean the link won't be linkified on Instagram,
# but false positives will cause the message to fail to send.
SIMPLE_URL_REGEX = re.compile(
    r"(?P<url>https?://[\da-z.-]+\.[a-z]{2,}(?:/[^\s]*)?)", flags=re.IGNORECASE
)


class UnsupportedAttachmentError(NotImplementedError):
    pass


class Portal(DBPortal, BasePortal):
    by_mxid: dict[RoomID, Portal] = {}
    by_thread_id: dict[tuple[str, int], Portal] = {}
    config: Config
    matrix: m.MatrixHandler
    az: AppService
    private_chat_portal_meta: bool

    _main_intent: IntentAPI | None
    _create_room_lock: asyncio.Lock
    backfill_lock: SimpleLock
    _msgid_dedup: deque[str]
    _reqid_dedup: set[str]

    _last_participant_update: set[int]
    _reaction_lock: asyncio.Lock
    _backfill_leave: set[IntentAPI] | None
    _typing: set[UserID]

    def __init__(
        self,
        thread_id: str,
        receiver: int,
        other_user_pk: int | None,
        mxid: RoomID | None = None,
        name: str | None = None,
        avatar_url: ContentURI | None = None,
        encrypted: bool = False,
        name_set: bool = False,
        avatar_set: bool = False,
        relay_user_id: UserID | None = None,
    ) -> None:
        super().__init__(
            thread_id,
            receiver,
            other_user_pk,
            mxid,
            name,
            avatar_url,
            encrypted,
            name_set,
            avatar_set,
            relay_user_id,
        )
        self._create_room_lock = asyncio.Lock()
        self.log = self.log.getChild(thread_id)
        self._msgid_dedup = deque(maxlen=100)
        self._reqid_dedup = set()
        self._last_participant_update = set()

        self.backfill_lock = SimpleLock(
            "Waiting for backfilling to finish before handling %s", log=self.log
        )
        self._backfill_leave = None
        self._main_intent = None
        self._reaction_lock = asyncio.Lock()
        self._typing = set()
        self._relay_user = None

    @property
    def is_direct(self) -> bool:
        return self.other_user_pk is not None

    @property
    def main_intent(self) -> IntentAPI:
        if not self._main_intent:
            raise ValueError("Portal must be postinit()ed before main_intent can be used")
        return self._main_intent

    @classmethod
    def init_cls(cls, bridge: "InstagramBridge") -> None:
        cls.config = bridge.config
        cls.matrix = bridge.matrix
        cls.az = bridge.az
        cls.loop = bridge.loop
        cls.bridge = bridge
        cls.private_chat_portal_meta = cls.config["bridge.private_chat_portal_meta"]
        NotificationDisabler.puppet_cls = p.Puppet
        NotificationDisabler.config_enabled = cls.config["bridge.backfill.disable_notifications"]

    # region Misc

    async def _send_delivery_receipt(self, event_id: EventID) -> None:
        if event_id and self.config["bridge.delivery_receipts"]:
            try:
                await self.az.intent.mark_read(self.mxid, event_id)
            except Exception:
                self.log.exception("Failed to send delivery receipt for %s", event_id)

    async def _send_bridge_success(
        self,
        sender: u.User,
        event_id: EventID,
        event_type: EventType,
        msgtype: MessageType | None = None,
    ) -> None:
        sender.send_remote_checkpoint(
            status=MessageSendCheckpointStatus.SUCCESS,
            event_id=event_id,
            room_id=self.mxid,
            event_type=event_type,
            message_type=msgtype,
        )
        asyncio.create_task(self._send_message_status(event_id, err=None))
        await self._send_delivery_receipt(event_id)

    async def _send_bridge_error(
        self,
        sender: u.User,
        err: Exception,
        event_id: EventID,
        event_type: EventType,
        message_type: MessageType | None = None,
        confirmed: bool = False,
    ) -> None:
        sender.send_remote_checkpoint(
            self._status_from_exception(err),
            event_id,
            self.mxid,
            event_type,
            message_type=message_type,
            error=err,
        )

        if self.config["bridge.delivery_error_reports"]:
            event_type_str = {
                EventType.REACTION: "reaction",
                EventType.ROOM_REDACTION: "redaction",
            }.get(event_type, "message")
            error_type = "was not" if confirmed else "may not have been"
            await self._send_message(
                self.main_intent,
                TextMessageEventContent(
                    msgtype=MessageType.NOTICE,
                    body=f"\u26a0 Your {event_type_str} {error_type} bridged: {str(err)}",
                ),
            )
        asyncio.create_task(self._send_message_status(event_id, err))

    async def _send_message_status(self, event_id: EventID, err: Exception | None) -> None:
        if not self.config["bridge.message_status_events"]:
            return
        intent = self.az.intent if self.encrypted else self.main_intent
        status = BeeperMessageStatusEventContent(
            network=self.bridge_info_state_key,
            relates_to=RelatesTo(
                rel_type=RelationType.REFERENCE,
                event_id=event_id,
            ),
        )
        if err:
            status.error = str(err)
            if isinstance(err, NotImplementedError):
                if isinstance(err, UnsupportedAttachmentError):
                    status.message = str(err)
                status.reason = MessageStatusReason.UNSUPPORTED
                status.status = MessageStatus.FAIL
            else:
                status.reason = MessageStatusReason.GENERIC_ERROR
                status.status = MessageStatus.RETRIABLE
        else:
            status.status = MessageStatus.SUCCESS
        status.fill_legacy_booleans()

        await intent.send_message_event(
            room_id=self.mxid,
            event_type=EventType.BEEPER_MESSAGE_STATUS,
            content=status,
        )

    async def _upsert_reaction(
        self,
        existing: DBReaction | None,
        intent: IntentAPI,
        mxid: EventID,
        message: DBMessage,
        sender: u.User | p.Puppet,
        reaction: str,
        mx_timestamp: int,
    ) -> None:
        if existing:
            self.log.debug(
                f"_upsert_reaction redacting {existing.mxid} and inserting {mxid}"
                f" (message: {message.mxid})"
            )
            await intent.redact(existing.mx_room, existing.mxid)
            await existing.edit(
                reaction=reaction, mxid=mxid, mx_room=message.mx_room, mx_timestamp=mx_timestamp
            )
        else:
            self.log.debug(f"_upsert_reaction inserting {mxid} (message: {message.mxid})")
            await DBReaction(
                mxid=mxid,
                mx_room=message.mx_room,
                ig_item_id=message.item_id,
                ig_receiver=self.receiver,
                ig_sender=sender.igpk,
                reaction=reaction,
                mx_timestamp=mx_timestamp,
            ).insert()

    # endregion
    # region Matrix event handling

    @staticmethod
    def _status_from_exception(e: Exception) -> MessageSendCheckpointStatus:
        if isinstance(e, NotImplementedError):
            return MessageSendCheckpointStatus.UNSUPPORTED
        return MessageSendCheckpointStatus.PERM_FAILURE

    async def handle_matrix_message(
        self, sender: u.User, message: MessageEventContent, event_id: EventID
    ) -> None:
        try:
            await self._handle_matrix_message(sender, message, event_id)
        except Exception as e:
            self.log.exception(f"Error handling Matrix event {event_id}")
            await self._send_bridge_error(
                sender,
                e,
                event_id,
                EventType.ROOM_MESSAGE,
                message_type=message.msgtype,
                confirmed=True,
            )
        else:
            await self._send_bridge_success(
                sender, event_id, EventType.ROOM_MESSAGE, message.msgtype
            )

    async def _handle_matrix_giphy(
        self,
        sender: u.User,
        event_id: EventID,
        request_id: str,
        giphy_id: str,
    ) -> CommandResponse:
        self.log.trace(f"Broadcasting giphy from {event_id} with request ID {request_id}")
        return await sender.client.broadcast(
            self.thread_id,
            ThreadItemType.ANIMATED_MEDIA,
            client_context=request_id,
            id=giphy_id,
        )

    async def _handle_matrix_image(
        self,
        sender: u.User,
        event_id: EventID,
        request_id: str,
        data: bytes,
        mime_type: str,
        width: int | None = None,
        height: int | None = None,
    ) -> CommandResponse:
        if mime_type != "image/jpeg":
            if Image is None:
                raise UnsupportedAttachmentError(
                    "Instagram does not allow non-JPEG images, and Pillow is not installed, "
                    "so the bridge couldn't convert the image automatically"
                )
            with BytesIO(data) as inp, BytesIO() as out:
                img = Image.open(inp)
                img.convert("RGB").save(out, format="JPEG", quality=80)
                data = out.getvalue()
                mime_type = "image/jpeg"

        self.log.trace(f"Uploading photo from {event_id} (mime: {mime_type})")
        upload_resp = await sender.client.upload_photo(
            data, mime=mime_type, width=width, height=height
        )
        self.log.trace(f"Broadcasting uploaded photo with request ID {request_id}")
        return await sender.client.broadcast(
            self.thread_id,
            ThreadItemType.CONFIGURE_PHOTO,
            client_context=request_id,
            upload_id=upload_resp.upload_id,
            allow_full_aspect_ratio="true",
        )

    async def _handle_matrix_video(
        self,
        sender: u.User,
        event_id: EventID,
        request_id: str,
        data: bytes,
        mime_type: str,
        duration: int | None = None,
        width: int | None = None,
        height: int | None = None,
    ) -> CommandResponse:
        if mime_type != "video/mp4":
            data = await ffmpeg.convert_bytes(
                data,
                output_extension=".mp4",
                output_args=("-c:v", "libx264", "-c:a", "aac"),
                input_mime=mime_type,
            )

        self.log.trace(f"Uploading video from {event_id}")
        _, upload_id = await sender.client.upload_mp4(
            data, duration_ms=duration, width=width, height=height
        )
        self.log.trace(f"Broadcasting uploaded video with request ID {request_id}")
        return await sender.client.broadcast(
            self.thread_id,
            ThreadItemType.CONFIGURE_VIDEO,
            client_context=request_id,
            upload_id=upload_id,
            video_result="",
        )

    async def _handle_matrix_audio(
        self,
        sender: u.User,
        event_id: EventID,
        request_id: str,
        data: bytes,
        mime_type: str,
        waveform: list[int],
        duration: int | None = None,
    ) -> CommandResponse:
        if mime_type != "audio/mp4":
            data = await ffmpeg.convert_bytes(
                data, output_extension=".m4a", output_args=("-c:a", "aac"), input_mime=mime_type
            )

        self.log.trace(f"Uploading audio from {event_id}")
        _, upload_id = await sender.client.upload_mp4(data, audio=True, duration_ms=duration)
        self.log.trace(f"Broadcasting uploaded audio with request ID {request_id}")
        return await sender.client.broadcast(
            self.thread_id,
            ThreadItemType.SHARE_VOICE,
            client_context=request_id,
            upload_id=upload_id,
            waveform=json.dumps([(part or 0) / 1024 for part in waveform], separators=(",", ":")),
            waveform_sampling_frequency_hz="10",
        )

    async def _handle_matrix_message(
        self, orig_sender: u.User, message: MessageEventContent, event_id: EventID
    ) -> None:
        sender, is_relay = await self.get_relay_sender(orig_sender, f"message {event_id}")
        assert sender, "user is not logged in"
        assert sender.is_connected, "You're not connected to Instagram"

        if is_relay:
            await self.apply_relay_message_format(orig_sender, message)

        reply_to = {}
        if message.get_reply_to():
            msg = await DBMessage.get_by_mxid(message.get_reply_to(), self.mxid)
            if msg and msg.client_context:
                reply_to = {
                    "replied_to_item_id": msg.item_id,
                    "replied_to_client_context": msg.client_context,
                }

        request_id = sender.state.gen_client_context()
        self._reqid_dedup.add(request_id)
        self.log.debug(
            f"Handling Matrix message {event_id} from {sender.mxid}/{sender.igpk} "
            f"with request ID {request_id}"
        )

        if message.msgtype == MessageType.NOTICE and not self.config["bridge.bridge_notices"]:
            return

        if message.msgtype in (MessageType.EMOTE, MessageType.TEXT, MessageType.NOTICE):
            text = message.body
            if message.msgtype == MessageType.EMOTE:
                text = f"/me {text}"
            self.log.trace(f"Sending Matrix text from {event_id} with request ID {request_id}")
            urls = SIMPLE_URL_REGEX.findall(text) or None
            if not self.is_direct:
                # Instagram groups don't seem to support sending link previews,
                # and the client_context-based deduplication breaks when trying to send them.
                urls = None
            resp = await sender.mqtt.send_text(
                self.thread_id, text=text, urls=urls, client_context=request_id, **reply_to
            )
        elif message.msgtype.is_media and "fi.mau.instagram.giphy_id" in message:
            resp = await self._handle_matrix_giphy(
                sender, event_id, request_id, message["fi.mau.instagram.giphy_id"]
            )
        elif message.msgtype.is_media:
            if message.file and decrypt_attachment:
                data = await self.main_intent.download_media(message.file.url)
                data = decrypt_attachment(
                    data, message.file.key.key, message.file.hashes.get("sha256"), message.file.iv
                )
            else:
                data = await self.main_intent.download_media(message.url)
            mime_type = message.info.mimetype or magic.from_buffer(data, mime=True)
            if message.msgtype == MessageType.IMAGE:
                resp = await self._handle_matrix_image(
                    sender,
                    event_id,
                    request_id,
                    data,
                    mime_type,
                    width=message.info.width,
                    height=message.info.height,
                )
            elif message.msgtype == MessageType.AUDIO:
                waveform = message.get("org.matrix.msc1767.audio", {}).get("waveform", [0] * 30)
                resp = await self._handle_matrix_audio(
                    sender,
                    event_id,
                    request_id,
                    data,
                    mime_type,
                    waveform,
                    duration=message.info.duration,
                )
            elif message.msgtype == MessageType.VIDEO:
                resp = await self._handle_matrix_video(
                    sender,
                    event_id,
                    request_id,
                    data,
                    mime_type,
                    duration=message.info.duration,
                    width=message.info.width,
                    height=message.info.height,
                )
            else:
                raise UnsupportedAttachmentError(
                    "Non-image/video/audio files are currently not supported"
                )
        else:
            raise NotImplementedError(f"Unknown message type {message.msgtype}")

        self.log.trace(f"Got response to message send {request_id}: {resp}")
        if resp.status != "ok":
            self.log.warning(f"Failed to handle {event_id}: {resp}")
            raise Exception(f"Failed to handle event. Error: {resp.payload.message}")
        else:
            self._msgid_dedup.appendleft(resp.payload.item_id)
            try:
                await DBMessage(
                    mxid=event_id,
                    mx_room=self.mxid,
                    item_id=resp.payload.item_id,
                    client_context=resp.payload.client_context,
                    receiver=self.receiver,
                    sender=sender.igpk,
                    ig_timestamp=int(resp.payload.timestamp),
                ).insert()
            except (asyncpg.UniqueViolationError, sqlite3.IntegrityError) as e:
                self.log.warning(
                    f"Error while persisting {event_id} ({resp.payload.client_context}) "
                    f"-> {resp.payload.item_id}: {e}"
                )
            self._reqid_dedup.remove(request_id)
            self.log.debug(
                f"Handled Matrix message {event_id} ({resp.payload.client_context}) "
                f"-> {resp.payload.item_id}"
            )

    async def handle_matrix_reaction(
        self, sender: u.User, event_id: EventID, reacting_to: EventID, emoji: str, timestamp: int
    ) -> None:
        try:
            await self._handle_matrix_reaction(sender, event_id, reacting_to, emoji, timestamp)
        except Exception as e:
            self.log.exception(f"Error handling Matrix reaction {event_id}")
            await self._send_bridge_error(
                sender,
                e,
                event_id,
                EventType.REACTION,
                confirmed=True,
            )
        else:
            await self._send_bridge_success(sender, event_id, EventType.REACTION)

    async def _handle_matrix_reaction(
        self, sender: u.User, event_id: EventID, reacting_to: EventID, emoji: str, timestamp: int
    ) -> None:
        if not await sender.is_logged_in():
            self.log.debug(f"Ignoring reaction by non-logged-in user {sender.mxid}")
            raise NotImplementedError("User is not logged in")

        message = await DBMessage.get_by_mxid(reacting_to, self.mxid)
        if not message or message.is_internal:
            self.log.debug(f"Ignoring reaction to unknown event {reacting_to}")
            await self.main_intent.redact(self.mxid, event_id, reason="Unknown target message")
            raise NotImplementedError("Unknown target message")

        existing = await DBReaction.get_by_item_id(message.item_id, message.receiver, sender.igpk)
        if existing and existing.reaction == emoji:
            return

        async with self._reaction_lock:
            resp = await sender.mqtt.send_reaction(
                self.thread_id, item_id=message.item_id, emoji=emoji
            )
            if resp.status != "ok":
                if resp.payload.message == "invalid unicode emoji":
                    # Instagram doesn't support this reaction. Notify the user, and redact it
                    # so that it doesn't get confusing.
                    await self.main_intent.redact(self.mxid, event_id, reason="Unsupported emoji")
                    raise NotImplementedError(f"Instagram does not support the {emoji} emoji.")
                raise Exception(f"Unknown response error: {resp}")

            self.log.trace(f"{sender.mxid} reacted to {message.item_id} with {emoji}")
            await self._upsert_reaction(
                existing, self.main_intent, event_id, message, sender, emoji, timestamp
            )

    async def handle_matrix_redaction(
        self, orig_sender: u.User, event_id: EventID, redaction_event_id: EventID
    ) -> None:
        sender = None
        try:
            sender, _ = await self.get_relay_sender(orig_sender, f"redaction {event_id}")
            if not sender:
                raise Exception("User is not logged in")

            await self._handle_matrix_redaction(sender, event_id)
        except Exception as e:
            self.log.exception(f"Error handling Matrix redaction {event_id}")
            await self._send_bridge_error(
                sender or orig_sender,
                e,
                redaction_event_id,
                EventType.ROOM_REDACTION,
                confirmed=True,
            )
        else:
            await self._send_bridge_success(sender, redaction_event_id, EventType.ROOM_REDACTION)

    async def _handle_matrix_redaction(self, sender: u.User, event_id: EventID) -> None:
        if not sender.is_connected:
            raise Exception("You're not connected to Instagram")

        reaction = await DBReaction.get_by_mxid(event_id, self.mxid)
        if reaction:
            try:
                await reaction.delete()
                await sender.mqtt.send_reaction(
                    self.thread_id,
                    item_id=reaction.ig_item_id,
                    reaction_status=ReactionStatus.DELETED,
                    emoji="",
                )
            except Exception as e:
                raise Exception(f"Removing reaction failed: {e}")
            else:
                self.log.trace(f"Removed reaction to {reaction.ig_item_id} after Matrix redaction")
            return

        message = await DBMessage.get_by_mxid(event_id, self.mxid)
        if message and not message.is_internal:
            try:
                await message.delete()
                await sender.client.delete_item(self.thread_id, message.item_id)
                self.log.trace(f"Removed {message} after Matrix redaction")
            except Exception as e:
                raise Exception(f"Removing message failed: {e}")
            else:
                self.log.trace(f"Removed message {message.item_id} after Matrix redaction")
            return

        raise NotImplementedError("No message or reaction found for redaction")

    async def handle_matrix_typing(self, users: set[UserID]) -> None:
        if users == self._typing:
            return
        old_typing = self._typing
        self._typing = users
        await self._handle_matrix_typing(old_typing - users, TypingStatus.OFF)
        await self._handle_matrix_typing(users - old_typing, TypingStatus.TEXT)

    async def _handle_matrix_typing(self, users: set[UserID], status: TypingStatus) -> None:
        for mxid in users:
            user = await u.User.get_by_mxid(mxid, create=False)
            if (
                not user
                or not await user.is_logged_in()
                or user.remote_typing_status == status
                or not user.is_connected
            ):
                continue
            user.remote_typing_status = None
            await user.mqtt.indicate_activity(self.thread_id, status)

    async def handle_matrix_leave(self, user: u.User) -> None:
        if not await user.is_logged_in():
            return
        if self.is_direct:
            self.log.info(f"{user.mxid} left private chat portal with {self.other_user_pk}")
            if user.igpk == self.receiver:
                self.log.info(
                    f"{user.mxid} was the recipient of this portal. Cleaning up and deleting..."
                )
                await self.cleanup_and_delete()
        else:
            self.log.debug(f"{user.mxid} left portal to {self.thread_id}")
            # TODO cleanup if empty

    # endregion
    # region Instagram event handling

    async def _reupload_instagram_media(
        self, source: u.User, media: RegularMediaItem, intent: IntentAPI
    ) -> MediaMessageEventContent:
        if media.media_type == MediaType.IMAGE:
            image = media.best_image
            if not image:
                raise ValueError("Attachment not available: didn't find photo URL")
            url = image.url
            msgtype = MessageType.IMAGE
            info = ImageInfo(height=image.height, width=image.width)
        elif media.media_type == MediaType.VIDEO:
            video = media.best_video
            if not video:
                raise ValueError("Attachment not available: didn't find video URL")
            url = video.url
            msgtype = MessageType.VIDEO
            info = VideoInfo(height=video.height, width=video.width)
        elif media.media_type == MediaType.CAROUSEL:
            raise ValueError(
                "Carousel media is not currently supported, "
                "please view the post on Instagram via the link below"
            )
        else:
            raise ValueError(
                f"Attachment not available: unsupported media type {media.media_type.human_name}"
            )
        return await self._reupload_instagram_file(source, url, msgtype, info, intent)

    async def _reupload_instagram_animated(
        self, source: u.User, media: AnimatedMediaItem, intent: IntentAPI
    ) -> MediaMessageEventContent:
        url = media.images.fixed_height.webp
        info = ImageInfo(
            height=int(media.images.fixed_height.height),
            width=int(media.images.fixed_height.width),
        )
        return await self._reupload_instagram_file(source, url, MessageType.IMAGE, info, intent)

    async def _reupload_instagram_voice(
        self, source: u.User, media: VoiceMediaItem, intent: IntentAPI
    ) -> MediaMessageEventContent:
        async def convert_to_ogg(data, mimetype):
            converted = await ffmpeg.convert_bytes(
                data, ".ogg", output_args=("-c:a", "libopus"), input_mime=mimetype
            )
            return converted, "audio/ogg"

        url = media.media.audio.audio_src
        info = AudioInfo(duration=media.media.audio.duration)
        waveform = [int(p * 1024) for p in media.media.audio.waveform_data]
        content = await self._reupload_instagram_file(
            source, url, MessageType.AUDIO, info, intent, convert_to_ogg
        )
        content["org.matrix.msc1767.audio"] = {
            "duration": media.media.audio.duration,
            "waveform": waveform,
        }
        content["org.matrix.msc3245.voice"] = {}
        return content

    async def _reupload_instagram_file(
        self,
        source: u.User,
        url: str,
        msgtype: MessageType | None,
        info: ImageInfo | VideoInfo | AudioInfo,
        intent: IntentAPI,
        convert_fn: Callable[[bytes, str], Awaitable[tuple[bytes, str]]] | None = None,
    ) -> MediaMessageEventContent:
        async with source.client.raw_http_get(url) as resp:
            try:
                length = int(resp.headers["Content-Length"])
            except KeyError:
                # TODO can the download be short-circuited if there's too much data?
                self.log.warning(
                    "Got file download response with no Content-Length header,"
                    "reading data dangerously"
                )
                length = 0
            if length > self.matrix.media_config.upload_size:
                self.log.debug(
                    f"{url} was too large ({length} > {self.matrix.media_config.upload_size})"
                )
                raise ValueError("Attachment not available: too large")
            data = await resp.read()
            info.mimetype = resp.headers["Content-Type"] or magic.from_buffer(data, mime=True)

        # Run the conversion function on the data.
        if convert_fn is not None:
            data, info.mimetype = await convert_fn(data, info.mimetype)

        info.size = len(data)
        extension = {
            "image/webp": ".webp",
            "image/jpeg": ".jpg",
            "video/mp4": ".mp4",
            "audio/mp4": ".m4a",
            "audio/ogg": ".ogg",
        }.get(info.mimetype)
        extension = extension or mimetypes.guess_extension(info.mimetype) or ""
        file_name = f"{msgtype.value[2:]}{extension}" if msgtype else None

        upload_mime_type = info.mimetype
        upload_file_name = file_name
        decryption_info = None
        if self.encrypted and encrypt_attachment:
            data, decryption_info = encrypt_attachment(data)
            upload_mime_type = "application/octet-stream"
            upload_file_name = None

        mxc = await intent.upload_media(
            data,
            mime_type=upload_mime_type,
            filename=upload_file_name,
            async_upload=self.config["homeserver.async_media"],
        )

        if decryption_info:
            decryption_info.url = mxc
            mxc = None

        return MediaMessageEventContent(
            body=file_name,
            external_url=url,
            url=mxc,
            file=decryption_info,
            info=info,
            msgtype=msgtype,
        )

    def _get_instagram_media_info(self, item: ThreadItem) -> tuple[MediaUploadFunc, MediaData]:
        # TODO maybe use a dict and item.item_type instead of a ton of ifs
        method = self._reupload_instagram_media
        if item.media:
            media_data = item.media
        elif item.visual_media:
            media_data = item.visual_media.media
        elif item.animated_media:
            media_data = item.animated_media
            method = self._reupload_instagram_animated
        elif item.voice_media:
            media_data = item.voice_media
            method = self._reupload_instagram_voice
        elif item.reel_share:
            media_data = item.reel_share.media
        elif item.story_share:
            media_data = item.story_share.media
        elif item.clip:
            media_data = item.clip.clip
        elif item.felix_share and item.felix_share.video:
            media_data = item.felix_share.video
        elif item.media_share:
            media_data = item.media_share
        elif item.direct_media_share:
            media_data = item.direct_media_share.media
        else:
            self.log.debug(f"Unknown media type in {item}")
            raise ValueError("Attachment not available: unsupported media type")
        if not media_data:
            self.log.debug(f"Didn't get media_data in {item}")
            raise ValueError("Attachment not available: unsupported media type")
        elif isinstance(media_data, ExpiredMediaItem):
            self.log.debug(f"Expired media in item {item}")
            raise ValueError("Attachment not available: media expired")
        return method, media_data

    async def _convert_instagram_media(
        self, source: u.User, intent: IntentAPI, item: ThreadItem
    ) -> MessageEventContent:
        try:
            reupload_func, media_data = self._get_instagram_media_info(item)
            content = await reupload_func(source, media_data, intent)
        except ValueError as e:
            content = TextMessageEventContent(body=str(e), msgtype=MessageType.NOTICE)
        except Exception:
            self.log.warning("Failed to upload media", exc_info=True)
            content = TextMessageEventContent(
                body="Attachment not available: failed to copy file", msgtype=MessageType.NOTICE
            )

        await self._add_instagram_reply(content, item.replied_to_message)
        return content

    async def _handle_instagram_media_share(
        self, source: u.User, intent: IntentAPI, item: ThreadItem
    ) -> EventID | None:
        item_type_name = None
        if item.media_share:
            share_item = item.media_share
        elif item.clip:
            share_item = item.clip.clip
            item_type_name = "clip"
        elif item.felix_share and item.felix_share.video:
            share_item = item.felix_share.video
        elif item.story_share:
            share_item = item.story_share.media
            item_type_name = "story"
        elif item.direct_media_share:
            share_item = item.direct_media_share.media
        else:
            return None
        item_type_name = item_type_name or share_item.media_type.human_name
        user_text = f"@{share_item.user.username}"
        user_link = (
            f'<a href="https://www.instagram.com/{share_item.user.username}/">{user_text}</a>'
        )
        prefix = TextMessageEventContent(
            msgtype=MessageType.NOTICE,
            format=Format.HTML,
            body=f"Sent {user_text}'s {item_type_name}",
            formatted_body=f"Sent {user_link}'s {item_type_name}",
        )
        if item.direct_media_share and item.direct_media_share.media_share_type == "tag":
            tagged_user_id = item.direct_media_share.tagged_user_id
            if tagged_user_id == source.igpk and share_item.user.pk == self.other_user_pk:
                prefix.body = prefix.formatted_body = "Tagged you in their post"
            elif share_item.user.pk == source.igpk and tagged_user_id == self.other_user_pk:
                prefix.body = prefix.formatted_body = "Tagged them in your post"

        content = await self._convert_instagram_media(source, intent, item)

        external_url = f"https://www.instagram.com/p/{share_item.code}/"
        if share_item.caption:
            caption_body = (
                f"> {share_item.caption.user.username}: {share_item.caption.text}\n\n"
                f"{external_url}"
            )
            caption_formatted_body = (
                f"<blockquote><strong>{share_item.caption.user.username}</strong>"
                f" {share_item.caption.text}</blockquote>"
                f'<a href="{external_url}">instagram.com/p/{share_item.code}</a>'
            )
        else:
            caption_body = external_url
            caption_formatted_body = (
                f'<a href="{external_url}">instagram.com/p/{share_item.code}</a>'
            )
        caption = TextMessageEventContent(
            msgtype=MessageType.TEXT,
            body=caption_body,
            formatted_body=caption_formatted_body,
            format=Format.HTML,
            external_url=external_url,
        )

        if self.bridge.config["bridge.caption_in_message"]:
            if isinstance(content, TextMessageEventContent):
                content.ensure_has_html()
                prefix.ensure_has_html()
                caption.ensure_has_html()
                combined = TextMessageEventContent(
                    msgtype=MessageType.TEXT,
                    body="\n".join((content.body, prefix.body, caption.body)),
                    formatted_body=(
                        f"<p><b>{content.formatted_body}</b></p>"
                        f"<p><i>{prefix.formatted_body}</p>"
                        f"<p>{caption.formatted_body}</p>"
                    ),
                    format=Format.HTML,
                    external_url=external_url,
                )
            else:
                prefix.ensure_has_html()
                caption.ensure_has_html()
                combined_body = "\n".join((prefix.body, caption.body))
                combined_formatted_body = (
                    f"<p><i>{prefix.formatted_body}</i></p><p>{caption.formatted_body}</p>"
                )

                combined = content
                combined["filename"] = content.body
                combined.body = combined_body
                combined["format"] = str(Format.HTML)
                combined["org.matrix.msc1767.caption"] = {
                    "org.matrix.msc1767.text": combined_body,
                    "org.matrix.msc1767.html": combined_formatted_body,
                }
                combined["formatted_body"] = combined_formatted_body

            event_id = await self._send_message(intent, combined, timestamp=item.timestamp_ms)
        else:
            await self._send_message(intent, prefix, timestamp=item.timestamp_ms)
            event_id = await self._send_message(intent, content, timestamp=item.timestamp_ms)
            await self._send_message(intent, caption, timestamp=item.timestamp_ms)

        return event_id

    async def _handle_instagram_reel_share(
        self, source: u.User, intent: IntentAPI, item: ThreadItem
    ) -> EventID | None:
        assert item.reel_share
        media = item.reel_share.media
        prefix_html = None
        if item.reel_share.type == ReelShareType.REPLY:
            if item.reel_share.reel_owner_id == source.igpk:
                prefix = "Replied to your story"
            else:
                username = media.user.username
                prefix = f"Sent @{username}'s story"
                user_link = f'<a href="https://www.instagram.com/{username}/">@{username}</a>'
                prefix_html = f"Sent {user_link}'s story"
        elif item.reel_share.type == ReelShareType.REACTION:
            if item.reel_share.reel_owner_id == source.igpk:
                prefix = "Reacted to your story"
            elif item.user_id == source.igpk:
                prefix = "You reacted to their story"
            else:
                prefix = "Reacted to a story"
        elif item.reel_share.type == ReelShareType.MENTION:
            if item.reel_share.mentioned_user_id == source.igpk:
                prefix = "Mentioned you in their story"
            else:
                prefix = "You mentioned them in your story"
        else:
            self.log.debug(f"Unsupported reel share type {item.reel_share.type}")
            return None
        prefix_content = TextMessageEventContent(msgtype=MessageType.NOTICE, body=prefix)
        if prefix_html:
            prefix_content.format = Format.HTML
            prefix_content.formatted_body = prefix_html
        caption_content = TextMessageEventContent(
            msgtype=MessageType.TEXT, body=item.reel_share.text
        )
        if not caption_content.body and isinstance(media, MediaShareItem):
            caption_content.body = media.caption.text if media.caption else ""
        if not caption_content.body:
            caption_content.body = "<no caption>"

        media_content = None
        fake_item_id = f"fi.mau.instagram.reel_share.{item.user_id}.{media.pk}"
        if isinstance(media, ExpiredMediaItem):
            media_content = TextMessageEventContent(
                msgtype=MessageType.NOTICE, body="Story expired"
            )
        else:
            existing = await DBMessage.get_by_item_id(fake_item_id, self.receiver)
            if existing:
                # If the user already reacted or replied to the same reel share item,
                # use a Matrix reply instead of reposting the image.
                caption_content.set_reply(existing.mxid)
            else:
                media_content = await self._convert_instagram_media(source, intent, item)

        if self.bridge.config["bridge.caption_in_message"]:
            if media_content:
                if isinstance(media_content, TextMessageEventContent):
                    media_content.ensure_has_html()
                    prefix_content.ensure_has_html()
                    caption_content.ensure_has_html()
                    combined = TextMessageEventContent(
                        msgtype=MessageType.TEXT,
                        body="\n".join(
                            (media_content.body, prefix_content.body, caption_content.body)
                        ),
                        formatted_body=(
                            f"<p><b>{media_content.formatted_body}</b></p>"
                            f"<p><i>{prefix_content.formatted_body}</i></p>"
                            f"<p>{caption_content.formatted_body}</p>",
                        ),
                        format=Format.HTML,
                    )
                else:
                    prefix_content.ensure_has_html()
                    caption_content.ensure_has_html()
                    combined_body = "\n".join((prefix_content.body, caption_content.body))
                    combined_formatted_body = (
                        f"<p><i>{prefix_content.formatted_body}</i></p>"
                        f"<p>{caption_content.formatted_body}</p>"
                    )

                    combined = media_content
                    combined["filename"] = combined.body
                    combined.body = combined_body
                    combined["format"] = str(Format.HTML)
                    combined["org.matrix.msc1767.caption"] = {
                        "org.matrix.msc1767.text": combined_body,
                        "org.matrix.msc1767.html": combined_formatted_body,
                    }
                    combined["formatted_body"] = combined_formatted_body
            else:
                combined = caption_content

            event_id = await self._send_message(intent, combined, timestamp=item.timestamp_ms)
        else:
            await self._send_message(intent, prefix_content, timestamp=item.timestamp_ms)
            if media_content:
                media_event_id = await self._send_message(
                    intent, media_content, timestamp=item.timestamp_ms
                )
                await DBMessage(
                    mxid=media_event_id,
                    mx_room=self.mxid,
                    item_id=fake_item_id,
                    client_context=None,
                    receiver=self.receiver,
                    sender=media.user.pk,
                    ig_timestamp=None,
                ).insert()
            event_id = await self._send_message(
                intent, caption_content, timestamp=item.timestamp_ms
            )
        return event_id

    async def _handle_instagram_link(
        self,
        source: u.User,
        intent: IntentAPI,
        item: ThreadItem,
    ) -> EventID:
        content = TextMessageEventContent(msgtype=MessageType.TEXT, body=item.link.text)
        link = item.link.link_context
        preview = {
            "og:url": link.link_url,
            "og:title": link.link_title,
            "og:description": link.link_summary,
        }
        if link.link_image_url:
            reuploaded = await self._reupload_instagram_file(
                source, link.link_image_url, msgtype=None, info=ImageInfo(), intent=intent
            )
            preview["og:image"] = reuploaded.url
            preview["og:image:type"] = reuploaded.info.mimetype
            preview["og:image:width"] = reuploaded.info.width
            preview["og:image:height"] = reuploaded.info.height
            preview["matrix:image:size"] = reuploaded.info.size
            if reuploaded.file:
                preview["beeper:image:encryption"] = reuploaded.file.serialize()
        preview = {k: v for k, v in preview.items() if v}
        content["com.beeper.linkpreviews"] = [preview] if "og:title" in preview else []
        await self._add_instagram_reply(content, item.replied_to_message)
        return await self._send_message(intent, content, timestamp=item.timestamp_ms)

    async def _handle_instagram_text(
        self, intent: IntentAPI, item: ThreadItem, text: str
    ) -> EventID:
        content = TextMessageEventContent(msgtype=MessageType.TEXT, body=text)
        content["com.beeper.linkpreviews"] = []
        await self._add_instagram_reply(content, item.replied_to_message)
        return await self._send_message(intent, content, timestamp=item.timestamp_ms)

    async def _send_instagram_unhandled(self, intent: IntentAPI, item: ThreadItem) -> EventID:
        content = TextMessageEventContent(
            msgtype=MessageType.NOTICE, body=f"Unsupported message type {item.item_type.value}"
        )
        await self._add_instagram_reply(content, item.replied_to_message)
        return await self._send_message(intent, content, timestamp=item.timestamp_ms)

    async def _handle_instagram_location(
        self, intent: IntentAPI, item: ThreadItem
    ) -> EventID | None:
        loc = item.location
        if not loc.lng or not loc.lat:
            # TODO handle somehow
            return None
        long_char = "E" if loc.lng > 0 else "W"
        lat_char = "N" if loc.lat > 0 else "S"

        body = (
            f"{loc.name} - {round(abs(loc.lat), 4)}° {lat_char}, "
            f"{round(abs(loc.lng), 4)}° {long_char}"
        )
        url = f"https://www.openstreetmap.org/#map=15/{loc.lat}/{loc.lng}"

        external_url = None
        if loc.external_source == "facebook_places":
            external_url = f"https://www.facebook.com/{loc.short_name}-{loc.facebook_places_id}"

        content = LocationMessageEventContent(
            msgtype=MessageType.LOCATION,
            geo_uri=f"geo:{loc.lat},{loc.lng}",
            body=f"Location: {body}\n{url}",
            external_url=external_url,
        )
        content["format"] = str(Format.HTML)
        content["formatted_body"] = f"Location: <a href='{url}'>{body}</a>"

        await self._add_instagram_reply(content, item.replied_to_message)

        return await self._send_message(intent, content, timestamp=item.timestamp_ms)

    async def _handle_instagram_profile(
        self, intent: IntentAPI, item: ThreadItem
    ) -> EventID | None:
        username = item.profile.username
        user_link = f'<a href="https://www.instagram.com/{username}/">@{username}</a>'
        text = f"Shared @{username}'s profile"
        html = f"Shared {user_link}'s profile"
        content = TextMessageEventContent(
            msgtype=MessageType.TEXT, format=Format.HTML, body=text, formatted_body=html
        )
        await self._add_instagram_reply(content, item.replied_to_message)
        return await self._send_message(intent, content, timestamp=item.timestamp_ms)

    async def handle_instagram_item(
        self, source: u.User, sender: p.Puppet, item: ThreadItem, is_backfill: bool = False
    ) -> None:
        try:
            await self._handle_instagram_item(source, sender, item, is_backfill)
        except Exception:
            self.log.exception("Fatal error handling Instagram item")
            self.log.trace("Item content: %s", item.serialize())

    async def _add_instagram_reply(
        self, content: MessageEventContent, reply_to: ThreadItem | None
    ) -> None:
        if not reply_to:
            return

        message = await DBMessage.get_by_item_id(reply_to.item_id, self.receiver)
        if not message:
            return

        content.set_reply(message.mxid)
        if not isinstance(content, TextMessageEventContent):
            return

        try:
            evt = await self.main_intent.get_event(message.mx_room, message.mxid)
        except (MNotFound, MForbidden):
            evt = None
        if not evt:
            return

        if evt.type == EventType.ROOM_ENCRYPTED:
            try:
                evt = await self.matrix.e2ee.decrypt(evt, wait_session_timeout=0)
            except SessionNotFound:
                return

        if isinstance(evt.content, TextMessageEventContent):
            evt.content.trim_reply_fallback()

        content.set_reply(evt)

    async def _handle_instagram_item(
        self, source: u.User, sender: p.Puppet, item: ThreadItem, is_backfill: bool = False
    ) -> None:
        if not isinstance(item, ThreadItem):
            # Parsing these items failed, they should have been logged already
            return

        client_context = item.client_context
        link_client_context = item.link.client_context if item.link else None
        cc = client_context
        if link_client_context:
            if not client_context:
                cc = f"link:{link_client_context}"
            elif client_context != link_client_context:
                cc = f"{client_context}/link:{link_client_context}"
        if client_context and client_context in self._reqid_dedup:
            self.log.debug(
                f"Ignoring message {item.item_id} ({cc}) by {item.user_id}"
                " as it was sent by us (client_context in dedup queue)"
            )
            return
        elif link_client_context and link_client_context in self._reqid_dedup:
            self.log.debug(
                f"Ignoring message {item.item_id} ({cc}) by {item.user_id}"
                " as it was sent by us (link.client_context in dedup queue)"
            )
            return

        if item.item_id in self._msgid_dedup:
            self.log.debug(
                f"Ignoring message {item.item_id} ({cc}) by {item.user_id}"
                " as it was already handled (message.id in dedup queue)"
            )
            return
        self._msgid_dedup.appendleft(item.item_id)

        if await DBMessage.get_by_item_id(item.item_id, self.receiver) is not None:
            self.log.debug(
                f"Ignoring message {item.item_id} ({cc}) by {item.user_id}"
                " as it was already handled (message.id in database)"
            )
            return

        self.log.debug(f"Starting handling of message {item.item_id} ({cc}) by {item.user_id}")
        asyncio.create_task(sender.intent_for(self).set_typing(self.mxid, is_typing=False))
        await self._handle_deduplicated_instagram_item(source, sender, item, is_backfill)

    async def _handle_deduplicated_instagram_item(
        self, source: u.User, sender: p.Puppet, item: ThreadItem, is_backfill: bool = False
    ) -> None:
        if self.backfill_lock.locked and sender.need_backfill_invite(self):
            self.log.debug("Adding %s's default puppet to room for backfilling", sender.mxid)
            if self.is_direct:
                await self.main_intent.invite_user(self.mxid, sender.default_mxid)
            intent = sender.default_mxid_intent
            await intent.ensure_joined(self.mxid)
            self._backfill_leave.add(intent)
        else:
            intent = sender.intent_for(self)
        event_id = None
        needs_handling = True
        if item.media or item.animated_media or item.voice_media or item.visual_media:
            content = await self._convert_instagram_media(source, intent, item)
            event_id = await self._send_message(intent, content, timestamp=item.timestamp_ms)
        elif item.location:
            event_id = await self._handle_instagram_location(intent, item)
        elif item.profile:
            event_id = await self._handle_instagram_profile(intent, item)
        elif item.reel_share:
            event_id = await self._handle_instagram_reel_share(source, intent, item)
        elif (
            item.media_share
            or item.direct_media_share
            or item.story_share
            or item.clip
            or item.felix_share
        ):
            event_id = await self._handle_instagram_media_share(source, intent, item)
        elif item.action_log:
            # These probably don't need to be bridged
            needs_handling = False
            self.log.debug(f"Ignoring action log message {item.item_id}")
        # TODO handle item.clip?
        if item.text:
            event_id = await self._handle_instagram_text(intent, item, item.text)
        elif item.like:
            # We handle likes as text because Matrix clients do big emoji on their own.
            event_id = await self._handle_instagram_text(intent, item, item.like)
        elif item.link:
            event_id = await self._handle_instagram_link(source, intent, item)
        handled = bool(event_id)
        if not event_id and needs_handling:
            self.log.debug(f"Unhandled Instagram message {item.item_id}")
            event_id = await self._send_instagram_unhandled(intent, item)

        cc = item.client_context
        if not cc and item.link and item.link.client_context:
            cc = item.link.client_context
        msg = DBMessage(
            mxid=event_id,
            mx_room=self.mxid,
            item_id=item.item_id,
            client_context=cc,
            receiver=self.receiver,
            sender=sender.pk,
            ig_timestamp=item.timestamp,
        )
        await msg.insert()
        await self._send_delivery_receipt(event_id)
        if handled:
            self.log.debug(f"Handled Instagram message {item.item_id} -> {event_id}")
        elif needs_handling:
            self.log.debug(
                f"Unhandled Instagram message {item.item_id} "
                f"(type {item.item_type} -> fallback error {event_id})"
            )
        if is_backfill and item.reactions:
            await self._handle_instagram_reactions(msg, item.reactions.emojis, is_backfill=True)

    async def handle_instagram_remove(self, item_id: str) -> None:
        message = await DBMessage.get_by_item_id(item_id, self.receiver)
        if message is None:
            return
        await message.delete()
        if message.mxid:
            sender = await p.Puppet.get_by_pk(message.sender)
            try:
                await sender.intent_for(self).redact(self.mxid, message.mxid)
            except MForbidden:
                await self.main_intent.redact(self.mxid, message.mxid)
            self.log.debug(f"Redacted {message.mxid} after Instagram unsend")

    async def handle_instagram_reaction(self, item: ThreadItem, remove: bool) -> None:
        sender = await p.Puppet.get_by_pk(item.new_reaction.sender_id)
        message = await DBMessage.get_by_item_id(item.item_id, self.receiver)
        if not message:
            self.log.debug(f"Dropping reaction by {sender.pk} to unknown message {item.item_id}")
            return
        emoji = item.new_reaction.emoji
        async with self._reaction_lock:
            existing = await DBReaction.get_by_item_id(item.item_id, self.receiver, sender.pk)
            if not existing and remove:
                self.log.debug(
                    f"Ignoring duplicate reaction removal by {sender.pk} to {item.item_id}"
                )
                return
            elif not remove and existing and existing.reaction == emoji:
                self.log.debug(f"Ignoring duplicate reaction by {sender.pk} to {item.item_id}")
                return
            intent = sender.intent_for(self)
            if remove:
                await existing.delete()
                await intent.redact(self.mxid, existing.mxid)
                self.log.debug(
                    f"Removed {sender.pk}'s reaction to {item.item_id} (redacted {existing.mxid})"
                )
            else:
                timestamp = item.new_reaction.timestamp_ms
                reaction_event_id = await intent.react(
                    self.mxid, message.mxid, key=emoji, timestamp=timestamp
                )
                await self._upsert_reaction(
                    existing, intent, reaction_event_id, message, sender, emoji, timestamp
                )
                self.log.debug(
                    f"Handled {sender.pk}'s reaction to {item.item_id} -> {reaction_event_id}"
                )

    async def _handle_instagram_reactions(
        self, message: DBMessage, reactions: list[Reaction], is_backfill: bool = False
    ) -> None:
        old_reactions: dict[int, DBReaction]
        old_reactions = {
            reaction.ig_sender: reaction
            for reaction in await DBReaction.get_all_by_item_id(message.item_id, self.receiver)
        }
        timestamp_deduplicator = 1
        for new_reaction in reactions:
            old_reaction = old_reactions.pop(new_reaction.sender_id, None)
            if old_reaction and old_reaction.reaction == new_reaction.emoji:
                continue
            puppet = await p.Puppet.get_by_pk(new_reaction.sender_id)
            intent = puppet.intent_for(self)
            timestamp = new_reaction.timestamp_ms if is_backfill else int(time.time() * 1000)
            if is_backfill:
                timestamp += timestamp_deduplicator
                timestamp_deduplicator += 1
            reaction_event_id = await intent.react(
                self.mxid, message.mxid, new_reaction.emoji, timestamp=timestamp
            )
            await self._upsert_reaction(
                old_reaction,
                intent,
                reaction_event_id,
                message,
                puppet,
                new_reaction.emoji,
                timestamp,
            )
        for old_reaction in old_reactions.values():
            await old_reaction.delete()
            puppet = await p.Puppet.get_by_pk(old_reaction.ig_sender)
            await puppet.intent_for(self).redact(self.mxid, old_reaction.mxid)

    async def handle_instagram_update(self, item: MessageSyncMessage) -> None:
        message = await DBMessage.get_by_item_id(item.item_id, self.receiver)
        if not message:
            return
        if item.has_seen:
            puppet = await p.Puppet.get_by_pk(item.has_seen, create=False)
            if puppet:
                await puppet.intent_for(self).mark_read(self.mxid, message.mxid)
        else:
            async with self._reaction_lock:
                await self._handle_instagram_reactions(
                    message, (item.reactions.emojis if item.reactions else [])
                )

    # endregion
    # region Updating portal info

    def _get_thread_name(self, thread: Thread) -> str:
        if self.is_direct:
            if self.other_user_pk == thread.viewer_id and len(thread.users) == 0:
                return "Instagram chat with yourself"
            elif len(thread.users) == 1:
                tpl = self.config["bridge.private_chat_name_template"]
                ui = thread.users[0]
                return tpl.format(displayname=ui.full_name, id=ui.pk, username=ui.username)
            pass
        elif thread.thread_title:
            return self.config["bridge.group_chat_name_template"].format(name=thread.thread_title)
        else:
            return ""

    async def update_info(self, thread: Thread, source: u.User) -> None:
        changed = await self._update_name(self._get_thread_name(thread))
        changed = await self._update_participants(thread.users, source) or changed
        if changed:
            await self.update_bridge_info()
            await self.update()
        # TODO update power levels with thread.admin_user_ids

    async def update_info_from_puppet(self, puppet: p.Puppet | None = None) -> None:
        if not self.is_direct:
            return
        if not puppet:
            puppet = await self.get_dm_puppet()
        await self._update_photo_from_puppet(puppet)
        if self.name and not self.name_set:
            await self._update_name(self.name)

    async def _update_name(self, name: str) -> bool:
        if name and (self.name != name or not self.name_set):
            self.name = name
            if self.mxid:
                try:
                    await self.main_intent.set_room_name(self.mxid, name)
                    self.name_set = True
                except Exception:
                    self.log.exception("Failed to update name")
                    self.name_set = False
            return True
        return False

    async def _update_photo_from_puppet(self, puppet: p.Puppet) -> bool:
        if not self.private_chat_portal_meta and not self.encrypted:
            return False
        if self.avatar_set and self.avatar_url == puppet.photo_mxc:
            return False
        self.avatar_url = puppet.photo_mxc
        if self.mxid:
            try:
                await self.main_intent.set_room_avatar(self.mxid, puppet.photo_mxc)
                self.avatar_set = True
            except Exception:
                self.log.exception("Failed to set room avatar")
                self.avatar_set = False
        return True

    async def _update_participants(self, users: list[ThreadUser], source: u.User) -> bool:
        meta_changed = False

        # Make sure puppets who should be here are here
        for user in users:
            puppet = await p.Puppet.get_by_pk(user.pk)
            await puppet.update_info(user, source)
            if self.mxid:
                await puppet.intent_for(self).ensure_joined(self.mxid)
            if puppet.pk == self.other_user_pk:
                meta_changed = await self._update_photo_from_puppet(puppet)

        if self.mxid:
            # Kick puppets who shouldn't be here
            current_members = {int(user.pk) for user in users}
            for user_id in await self.main_intent.get_room_members(self.mxid):
                pk = p.Puppet.get_id_from_mxid(user_id)
                if pk and pk not in current_members and pk != self.other_user_pk:
                    await self.main_intent.kick_user(
                        self.mxid,
                        p.Puppet.get_mxid_from_id(pk),
                        reason="User had left this Instagram DM",
                    )

        return meta_changed

    async def _update_read_receipts(self, receipts: dict[int | str, ThreadUserLastSeenAt]) -> None:
        for user_id, receipt in receipts.items():
            message: DBMessage | DBReaction
            message = await DBMessage.get_by_item_id(receipt.item_id, self.receiver)
            if not message:
                reaction: DBReaction
                message, reaction = await asyncio.gather(
                    DBMessage.get_closest(self.mxid, int(receipt.timestamp)),
                    DBReaction.get_closest(self.mxid, receipt.timestamp_ms),
                )
                if (not message or not message.mxid) and not reaction:
                    self.log.debug(
                        "Couldn't find message %s to mark as read by %s", receipt, user_id
                    )
                    continue
                elif not message or (reaction and reaction.mx_timestamp > message.ig_timestamp_ms):
                    message = reaction
            puppet = await p.Puppet.get_by_pk(int(user_id), create=False)
            if not puppet:
                continue
            try:
                await puppet.intent_for(self).mark_read(message.mx_room, message.mxid)
            except Exception:
                self.log.warning(
                    f"Failed to mark {message.mxid} in {message.mx_room} "
                    f"as read by {puppet.intent.mxid}",
                    exc_info=True,
                )

    async def get_dm_puppet(self) -> p.Puppet | None:
        if not self.is_direct:
            return None
        return await p.Puppet.get_by_pk(self.other_user_pk)

    # endregion
    # region Backfilling

    async def backfill(self, source: u.User, thread: Thread, is_initial: bool = False) -> None:
        limit = (
            self.config["bridge.backfill.initial_limit"]
            if is_initial
            else self.config["bridge.backfill.missed_limit"]
        )
        if limit == 0:
            return
        elif limit < 0:
            limit = None
        with self.backfill_lock:
            await self._backfill(source, thread, is_initial, limit)

    async def _backfill(
        self, source: u.User, thread: Thread, is_initial: bool, limit: int
    ) -> None:
        self.log.debug("Backfilling history through %s", source.mxid)

        entries = await self._fetch_backfill_items(source, thread, is_initial, limit)
        if not entries:
            self.log.debug("Didn't get any items to backfill from server")
            return

        self.log.debug("Got %d entries from server", len(entries))

        self._backfill_leave = set()
        async with NotificationDisabler(self.mxid, source):
            for entry in reversed(entries):
                sender = await p.Puppet.get_by_pk(int(entry.user_id))
                await self.handle_instagram_item(source, sender, entry, is_backfill=True)
        for intent in self._backfill_leave:
            self.log.trace("Leaving room with %s post-backfill", intent.mxid)
            await intent.leave_room(self.mxid)
        self._backfill_leave = None
        self.log.info("Backfilled %d messages through %s", len(entries), source.mxid)

    async def _fetch_backfill_items(
        self, source: u.User, thread: Thread, is_initial: bool, limit: int
    ) -> list[ThreadItem]:
        items = []
        excluded_count = 0
        self.log.debug("Fetching up to %d messages through %s", limit, source.igpk)
        async for item in source.client.iter_thread(self.thread_id, start_at=thread):
            if len(items) - excluded_count >= limit:
                self.log.debug(f"Fetched {len(items)} messages (the limit)")
                break
            elif not is_initial:
                msg = await DBMessage.get_by_item_id(item.item_id, receiver=self.receiver)
                if msg is not None:
                    self.log.debug(
                        f"Fetched {len(items)} messages and hit a message"
                        " that's already in the database."
                    )
                    break
            elif not item.is_handleable:
                self.log.debug(
                    f"Not counting {item.unhandleable_type} item {item.item_id}"
                    " against backfill limit"
                )
                excluded_count += 1
            items.append(item)
        return items

    # endregion
    # region Bridge info state event

    @property
    def bridge_info_state_key(self) -> str:
        return f"net.maunium.instagram://instagram/{self.thread_id}"

    @property
    def bridge_info(self) -> dict[str, Any]:
        return {
            "bridgebot": self.az.bot_mxid,
            "creator": self.main_intent.mxid,
            "protocol": {
                "id": "instagram",
                "displayname": "Instagram DM",
                "avatar_url": self.config["appservice.bot_avatar"],
            },
            "channel": {
                "id": self.thread_id,
                "displayname": self.name,
                "avatar_url": self.avatar_url,
            },
        }

    async def update_bridge_info(self) -> None:
        if not self.mxid:
            self.log.debug("Not updating bridge info: no Matrix room created")
            return
        try:
            self.log.debug("Updating bridge info...")
            await self.main_intent.send_state_event(
                self.mxid, StateBridge, self.bridge_info, self.bridge_info_state_key
            )
            # TODO remove this once https://github.com/matrix-org/matrix-doc/pull/2346 is in spec
            await self.main_intent.send_state_event(
                self.mxid, StateHalfShotBridge, self.bridge_info, self.bridge_info_state_key
            )
        except Exception:
            self.log.warning("Failed to update bridge info", exc_info=True)

    # endregion
    # region Creating Matrix rooms

    async def create_matrix_room(self, source: u.User, info: Thread) -> RoomID | None:
        if self.mxid:
            try:
                await self.update_matrix_room(source, info)
            except Exception:
                self.log.exception("Failed to update portal")
            return self.mxid
        async with self._create_room_lock:
            return await self._create_matrix_room(source, info)

    def _get_invite_content(self, double_puppet: p.Puppet | None) -> dict[str, bool]:
        invite_content = {}
        if double_puppet:
            invite_content["fi.mau.will_auto_accept"] = True
        if self.is_direct:
            invite_content["is_direct"] = True
        return invite_content

    async def update_matrix_room(
        self, source: u.User, info: Thread, backfill: bool = False
    ) -> None:
        puppet = await p.Puppet.get_by_custom_mxid(source.mxid)
        await self.main_intent.invite_user(
            self.mxid,
            source.mxid,
            check_cache=True,
            extra_content=self._get_invite_content(puppet),
        )
        if puppet:
            did_join = await puppet.intent.ensure_joined(self.mxid)
            if did_join and self.is_direct:
                await source.update_direct_chats({self.main_intent.mxid: [self.mxid]})

        await self.update_info(info, source)

        if backfill:
            last_msg = await DBMessage.get_by_item_id(
                info.last_permanent_item.item_id, receiver=self.receiver
            )
            if last_msg is None:
                self.log.debug(
                    f"Last permanent item ({info.last_permanent_item.item_id})"
                    " not found in database, starting backfilling"
                )
                await self.backfill(source, thread=info, is_initial=False)
        await self._update_read_receipts(info.last_seen_at)

    async def _create_matrix_room(self, source: u.User, info: Thread) -> RoomID | None:
        if self.mxid:
            await self.update_matrix_room(source, info)
            return self.mxid
        await self.update_info(info, source)
        self.log.debug("Creating Matrix room")
        name: str | None = None
        initial_state = [
            {
                "type": str(StateBridge),
                "state_key": self.bridge_info_state_key,
                "content": self.bridge_info,
            },
            # TODO remove this once https://github.com/matrix-org/matrix-doc/pull/2346 is in spec
            {
                "type": str(StateHalfShotBridge),
                "state_key": self.bridge_info_state_key,
                "content": self.bridge_info,
            },
        ]
        invites = []
        if self.config["bridge.encryption.default"] and self.matrix.e2ee:
            self.encrypted = True
            initial_state.append(
                {
                    "type": "m.room.encryption",
                    "content": self.get_encryption_state_event_json(),
                }
            )
            if self.is_direct:
                invites.append(self.az.bot_mxid)
        if self.encrypted or self.private_chat_portal_meta or not self.is_direct:
            name = self.name

        # We lock backfill lock here so any messages that come between the room being created
        # and the initial backfill finishing wouldn't be bridged before the backfill messages.
        with self.backfill_lock:
            creation_content = {}
            if not self.config["bridge.federate_rooms"]:
                creation_content["m.federate"] = False
            self.mxid = await self.main_intent.create_room(
                name=name,
                is_direct=self.is_direct,
                initial_state=initial_state,
                invitees=invites,
                creation_content=creation_content,
            )
            if not self.mxid:
                raise Exception("Failed to create room: no mxid returned")

            if self.encrypted and self.matrix.e2ee and self.is_direct:
                try:
                    await self.az.intent.ensure_joined(self.mxid)
                except Exception:
                    self.log.warning(f"Failed to add bridge bot to new private chat {self.mxid}")

            await self.update()
            self.log.debug(f"Matrix room created: {self.mxid}")
            self.by_mxid[self.mxid] = self

            puppet = await p.Puppet.get_by_custom_mxid(source.mxid)
            await self.main_intent.invite_user(
                self.mxid, source.mxid, extra_content=self._get_invite_content(puppet)
            )
            if puppet:
                try:
                    if self.is_direct:
                        await source.update_direct_chats({self.main_intent.mxid: [self.mxid]})
                    await puppet.intent.join_room_by_id(self.mxid)
                except MatrixError:
                    self.log.debug(
                        "Failed to join custom puppet into newly created portal", exc_info=True
                    )

            await self._update_participants(info.users, source)

            try:
                await self.backfill(source, thread=info, is_initial=True)
            except Exception:
                self.log.exception("Failed to backfill new portal")
            await self._update_read_receipts(info.last_seen_at)

        return self.mxid

    # endregion
    # region Database getters

    async def postinit(self) -> None:
        self.by_thread_id[(self.thread_id, self.receiver)] = self
        if self.mxid:
            self.by_mxid[self.mxid] = self
        self._main_intent = (
            (await p.Puppet.get_by_pk(self.other_user_pk)).default_mxid_intent
            if self.other_user_pk
            else self.az.intent
        )

    async def delete(self) -> None:
        await DBMessage.delete_all(self.mxid)
        self.by_mxid.pop(self.mxid, None)
        self.mxid = None
        self.encrypted = False
        await self.update()

    async def save(self) -> None:
        await self.update()

    @classmethod
    def all_with_room(cls) -> AsyncGenerator[Portal, None]:
        return cls._db_to_portals(super().all_with_room())

    @classmethod
    def find_private_chats_with(cls, other_user: int) -> AsyncGenerator[Portal, None]:
        return cls._db_to_portals(super().find_private_chats_with(other_user))

    @classmethod
    async def find_private_chat(cls, receiver: int, other_user: int) -> Portal | None:
        thread_id = await super().find_private_chat_id(receiver, other_user)
        if not thread_id:
            return None
        return await cls.get_by_thread_id(thread_id, receiver=receiver, is_group=False)

    @classmethod
    async def _db_to_portals(cls, query: Awaitable[list[Portal]]) -> AsyncGenerator[Portal, None]:
        portals = await query
        for index, portal in enumerate(portals):
            try:
                yield cls.by_thread_id[(portal.thread_id, portal.receiver)]
            except KeyError:
                await portal.postinit()
                yield portal

    @classmethod
    @async_getter_lock
    async def get_by_mxid(cls, mxid: RoomID) -> Portal | None:
        try:
            return cls.by_mxid[mxid]
        except KeyError:
            pass

        portal = cast(cls, await super().get_by_mxid(mxid))
        if portal is not None:
            await portal.postinit()
            return portal

        return None

    @classmethod
    @async_getter_lock
    async def get_by_thread_id(
        cls,
        thread_id: str,
        *,
        receiver: int,
        is_group: bool | None = None,
        other_user_pk: int | None = None,
    ) -> Portal | None:
        if is_group and receiver != 0:
            receiver = 0
        try:
            return cls.by_thread_id[(thread_id, receiver)]
        except KeyError:
            pass
        if is_group is None and receiver != 0:
            try:
                return cls.by_thread_id[(thread_id, 0)]
            except KeyError:
                pass

        portal = cast(
            cls,
            await super().get_by_thread_id(
                thread_id, receiver=receiver, rec_must_match=is_group is not None
            ),
        )
        if portal is not None:
            await portal.postinit()
            return portal

        if is_group is not None:
            portal = cls(thread_id, receiver, other_user_pk=other_user_pk)
            await portal.insert()
            await portal.postinit()
            return portal

        return None

    @classmethod
    async def get_by_thread(cls, thread: Thread, receiver: int) -> Portal | None:
        if thread.is_group:
            receiver = 0
            other_user_pk = None
        else:
            if len(thread.users) == 0:
                other_user_pk = receiver
            else:
                other_user_pk = thread.users[0].pk
        return await cls.get_by_thread_id(
            thread.thread_id,
            receiver=receiver,
            is_group=thread.is_group,
            other_user_pk=other_user_pk,
        )

    # endregion