diff --git a/matrix_appservice_kakaotalk/db/message.py b/matrix_appservice_kakaotalk/db/message.py
index 30ebb0c..ed01c36 100644
--- a/matrix_appservice_kakaotalk/db/message.py
+++ b/matrix_appservice_kakaotalk/db/message.py
@@ -21,7 +21,7 @@ from asyncpg import Record
 from attr import dataclass, field
 
 from mautrix.types import EventID, RoomID
-from mautrix.util.async_db import Database
+from mautrix.util.async_db import Database, Scheme
 
 from ..kt.types.bson import Long
 
@@ -101,6 +101,30 @@ class Message:
         "VALUES ($1, $2, $3, $4, $5, $6, $7)"
     )
 
+    @classmethod
+    async def bulk_create(
+        cls,
+        ktid: str,
+        kt_chat: int,
+        kt_receiver: int,
+        event_ids: list[EventID],
+        timestamp: int,
+        mx_room: RoomID,
+    ) -> None:
+        if not event_ids:
+            return
+        columns = [col.strip('"') for col in cls.columns.split(", ")]
+        records = [
+            (mxid, mx_room, ktid, index, kt_chat, kt_receiver, timestamp)
+            for index, mxid in enumerate(event_ids)
+        ]
+        async with cls.db.acquire() as conn, conn.transaction():
+            if cls.db.scheme == Scheme.POSTGRES:
+                await conn.copy_records_to_table("message", records=records, columns=columns)
+            else:
+                await conn.executemany(cls._insert_query, records)
+
+
     async def insert(self) -> None:
         q = self._insert_query
         await self.db.execute(
diff --git a/matrix_appservice_kakaotalk/kt/client/client.py b/matrix_appservice_kakaotalk/kt/client/client.py
index 0e374c9..c93800c 100644
--- a/matrix_appservice_kakaotalk/kt/client/client.py
+++ b/matrix_appservice_kakaotalk/kt/client/client.py
@@ -23,7 +23,7 @@ with any other potential backend.
 from __future__ import annotations
 
 from typing import TYPE_CHECKING, cast, Type, Optional, Union
-
+from contextlib import asynccontextmanager
 import logging
 import urllib.request
 
@@ -65,6 +65,12 @@ if TYPE_CHECKING:
     from ...user import User
 
 
+@asynccontextmanager
+async def sandboxed_get(url: URL) -> _RequestContextManager:
+    async with ClientSession() as sess, sess.get(url) as resp:
+        yield resp
+
+
 # TODO Consider defining an interface for this, with node/native backend as swappable implementations
 # TODO If no state is stored, consider using free functions instead of classmethods
 class Client:
@@ -154,6 +160,7 @@ class Client:
         self,
         url: Union[str, URL],
         headers: Optional[dict[str, str]] = None,
+        sandbox: bool = False,
         **kwargs,
     ) -> _RequestContextManager:
         # TODO Is auth ever needed?
@@ -163,6 +170,8 @@ class Client:
             **(headers or {}),
         }
         url = URL(url)
+        if sandbox:
+            return sandboxed_get(url)
         return self.http.get(url, headers=headers, **kwargs)
 
     # endregion
diff --git a/matrix_appservice_kakaotalk/kt/types/chat/__init__.py b/matrix_appservice_kakaotalk/kt/types/chat/__init__.py
index c0eff5d..b3fa5a2 100644
--- a/matrix_appservice_kakaotalk/kt/types/chat/__init__.py
+++ b/matrix_appservice_kakaotalk/kt/types/chat/__init__.py
@@ -13,7 +13,6 @@
 #
 # 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 .attachment import *
 from .chat_type import *
 from .chat import *
-"""
diff --git a/matrix_appservice_kakaotalk/kt/types/attachment/__init__.py b/matrix_appservice_kakaotalk/kt/types/chat/attachment/__init__.py
similarity index 74%
rename from matrix_appservice_kakaotalk/kt/types/attachment/__init__.py
rename to matrix_appservice_kakaotalk/kt/types/chat/attachment/__init__.py
index 0b590cb..f034f85 100644
--- a/matrix_appservice_kakaotalk/kt/types/attachment/__init__.py
+++ b/matrix_appservice_kakaotalk/kt/types/chat/attachment/__init__.py
@@ -19,8 +19,7 @@ from attr import dataclass
 
 from mautrix.types import SerializableAttrs
 
-from ..bson import Long
-from .mention import MentionStruct
+from .mention import *
 
 
 @dataclass(kw_only=True)
@@ -28,9 +27,28 @@ class Attachment(SerializableAttrs):
     shout: Optional[bool] = None
     mentions: Optional[list[MentionStruct]] = None
     urls: Optional[list[str]] = None
+    url: Optional[str] = None # NOTE Added since this may have replaced urls
 
 
 @dataclass
 class PathAttachment(Attachment):
     path: str
     s: int
+
+
+from .media import *
+from .reply import *
+from .media import *
+from .emoticon import *
+#from .voip import *
+from .contact import *
+from .map import *
+from .post import *
+from .openlink import *
+
+
+__all__ = [
+    "Attachment",
+    "PathAttachment",
+]
+# TODO What about the import *s?
diff --git a/matrix_appservice_kakaotalk/kt/types/chat/attachment/contact.py b/matrix_appservice_kakaotalk/kt/types/chat/attachment/contact.py
new file mode 100644
index 0000000..66db832
--- /dev/null
+++ b/matrix_appservice_kakaotalk/kt/types/chat/attachment/contact.py
@@ -0,0 +1,42 @@
+# matrix-appservice-kakaotalk - A Matrix-KakaoTalk puppeting bridge.
+# Copyright (C) 2022 Tulir Asokan, Andrew Ferrazzutti
+#
+# 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 typing import Union
+
+from attr import dataclass
+
+from ...bson import Long
+from . import Attachment
+
+
+@dataclass
+class ProfileAttachment(Attachment):
+    userId: Union[int, Long]
+    nickName: str
+    fullProfileImageUrl: str
+    profileImageUrl: str
+    statusMessage: str
+
+
+@dataclass
+class ContactAttachment(Attachment):
+    name: str
+    url: str
+
+
+__all__ = [
+    "ProfileAttachment",
+    "ContactAttachment",
+]
diff --git a/matrix_appservice_kakaotalk/kt/types/chat/attachment/emoticon.py b/matrix_appservice_kakaotalk/kt/types/chat/attachment/emoticon.py
new file mode 100644
index 0000000..5a81518
--- /dev/null
+++ b/matrix_appservice_kakaotalk/kt/types/chat/attachment/emoticon.py
@@ -0,0 +1,37 @@
+# matrix-appservice-kakaotalk - A Matrix-KakaoTalk puppeting bridge.
+# Copyright (C) 2022 Tulir Asokan, Andrew Ferrazzutti
+#
+# 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 typing import Optional
+
+from attr import dataclass
+
+from . import Attachment
+
+
+@dataclass
+class EmoticonAttachment(Attachment):
+    path: str
+    name: str
+    type: str
+    alt: str
+    s: Optional[int] = None
+    sound: Optional[str] = None
+    width: Optional[int] = None
+    height: Optional[int] = None
+
+
+__all__ = [
+    "EmoticonAttachment",
+]
diff --git a/matrix_appservice_kakaotalk/kt/types/chat/attachment/map.py b/matrix_appservice_kakaotalk/kt/types/chat/attachment/map.py
new file mode 100644
index 0000000..6084936
--- /dev/null
+++ b/matrix_appservice_kakaotalk/kt/types/chat/attachment/map.py
@@ -0,0 +1,31 @@
+# matrix-appservice-kakaotalk - A Matrix-KakaoTalk puppeting bridge.
+# Copyright (C) 2022 Tulir Asokan, Andrew Ferrazzutti
+#
+# 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 attr import dataclass
+
+from . import Attachment
+
+
+@dataclass
+class MapAttachment(Attachment):
+    lat: int
+    lng: int
+    a: str
+    c: bool
+
+
+__all__ = [
+    "MapAttachment",
+]
diff --git a/matrix_appservice_kakaotalk/kt/types/chat/attachment/media.py b/matrix_appservice_kakaotalk/kt/types/chat/attachment/media.py
new file mode 100644
index 0000000..0bf831d
--- /dev/null
+++ b/matrix_appservice_kakaotalk/kt/types/chat/attachment/media.py
@@ -0,0 +1,93 @@
+# matrix-appservice-kakaotalk - A Matrix-KakaoTalk puppeting bridge.
+# Copyright (C) 2022 Tulir Asokan, Andrew Ferrazzutti
+#
+# 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 typing import Optional
+
+from attr import dataclass
+
+from . import Attachment
+
+
+@dataclass
+class MediaKeyAttachment(Attachment):
+    k: str
+    url: str
+    s: int
+
+
+@dataclass
+class PhotoAttachment(Attachment):
+    w: int
+    h: int
+    thumbnailUrl: str
+    thumbnailWidth: int
+    thumbnailHeight: int
+    cs: str
+    mt: str
+
+
+@dataclass
+class MultiPhotoAttachment(Attachment):
+    kl: list[str]
+    wl: list[int]
+    hl: list[int]
+    csl: list[str]
+    imageUrls: list[str]
+    thumbnailUrls: list[str]
+    thumbnailWidths: list[int]
+    thumbnailHeights: list[int]
+    sl: int
+
+
+@dataclass
+class VideoAttachment(Attachment):
+    tk: str
+    w: int
+    h: int
+    cs: str
+    d: int
+
+
+@dataclass
+class FileAttachment(Attachment):
+    name: str
+    size: int
+    expire: int
+    cs: str
+
+
+@dataclass
+class AudioAttachment(Attachment):
+    d: int
+    expire: Optional[int] = None
+
+
+@dataclass
+class LongTextAttachment(Attachment):
+    path: str
+    k: str
+    s: int
+    sd: bool
+
+
+__all__ = [
+    "MediaKeyAttachment",
+    "PhotoAttachment",
+    "MultiPhotoAttachment",
+    "VideoAttachment",
+    "FileAttachment",
+    "AudioAttachment",
+    "LongTextAttachment",
+]
diff --git a/matrix_appservice_kakaotalk/kt/types/attachment/mention.py b/matrix_appservice_kakaotalk/kt/types/chat/attachment/mention.py
similarity index 94%
rename from matrix_appservice_kakaotalk/kt/types/attachment/mention.py
rename to matrix_appservice_kakaotalk/kt/types/chat/attachment/mention.py
index c151b1c..1006891 100644
--- a/matrix_appservice_kakaotalk/kt/types/attachment/mention.py
+++ b/matrix_appservice_kakaotalk/kt/types/chat/attachment/mention.py
@@ -19,7 +19,7 @@ from attr import dataclass
 
 from mautrix.types import SerializableAttrs
 
-from ..bson import Long
+from ...bson import Long
 
 
 @dataclass
@@ -27,3 +27,8 @@ class MentionStruct(SerializableAttrs):
     at: list[int]
     len: int
     user_id: Union[Long, int]
+
+
+__all__ = [
+    "MentionStruct",
+]
diff --git a/matrix_appservice_kakaotalk/kt/types/chat/attachment/openlink.py b/matrix_appservice_kakaotalk/kt/types/chat/attachment/openlink.py
new file mode 100644
index 0000000..cead03a
--- /dev/null
+++ b/matrix_appservice_kakaotalk/kt/types/chat/attachment/openlink.py
@@ -0,0 +1,30 @@
+# matrix-appservice-kakaotalk - A Matrix-KakaoTalk puppeting bridge.
+# Copyright (C) 2022 Tulir Asokan, Andrew Ferrazzutti
+#
+# 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 attr import dataclass
+
+from .post import PostAttachment
+
+
+@dataclass
+class OpenScheduleAttachment(PostAttachment):
+    scheduleId: int
+    title: str
+    eventAt: int
+
+
+__all__ = [
+    "OpenScheduleAttachment",
+]
diff --git a/matrix_appservice_kakaotalk/kt/types/chat/attachment/post.py b/matrix_appservice_kakaotalk/kt/types/chat/attachment/post.py
new file mode 100644
index 0000000..2ea9c83
--- /dev/null
+++ b/matrix_appservice_kakaotalk/kt/types/chat/attachment/post.py
@@ -0,0 +1,141 @@
+# matrix-appservice-kakaotalk - A Matrix-KakaoTalk puppeting bridge.
+# Copyright (C) 2022 Tulir Asokan, Andrew Ferrazzutti
+#
+# 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 typing import Optional, Union
+from enum import IntEnum
+
+from attr import dataclass
+
+from mautrix.types import SerializableAttrs
+
+from ...bson import Long
+from . import Attachment
+from .emoticon import EmoticonAttachment
+
+
+class KnownPostItemType(IntEnum):
+    TEXT = 1
+    FOOTER = 2
+    HEADER = 3
+    EMOTICON = 4
+    IMAGE = 5
+    VIDEO = 6
+    FILE = 7
+    SCHEDULE = 8
+    VOTE = 9
+    SCRAP = 10
+
+PostItemType = Union[KnownPostItemType, int]
+
+
+class KnownPostSubItemType(IntEnum):
+    pass
+
+PostSubItemType = Union[KnownPostSubItemType, int]
+
+
+class KnownPostFooterStyle(IntEnum):
+    ARTICLE = 1
+    SCHEDULE = 2
+    SCHEDULE_ANSWER = 3
+    VOTE = 4
+    VOTE_RESULT = 5
+
+PostFooterStyle = Union[KnownPostFooterStyle, int]
+
+
+class PostItem:
+    @dataclass
+    class Unknown(SerializableAttrs):
+        t: PostItemType
+
+    @dataclass(kw_only=True)
+    class Text(Unknown):
+        t = KnownPostItemType.TEXT
+        ct: str
+        jct: str
+
+    @dataclass(kw_only=True)
+    class Header(Unknown):
+        t = KnownPostItemType.HEADER
+        st: int
+
+        @dataclass
+        class UDict(SerializableAttrs):
+            id: Union[int, Long]
+
+        u: Optional[UDict]
+
+    @dataclass(kw_only=True)
+    class Image(Unknown):
+        t = KnownPostItemType.IMAGE
+        tt: Optional[str] = None
+        th: list[str]
+        g: Optional[bool] = None
+
+    @dataclass(kw_only=True)
+    class Emoticon(Unknown):
+        t = KnownPostItemType.EMOTICON
+        ct: EmoticonAttachment
+
+    @dataclass(kw_only=True)
+    class Vote(Unknown):
+        t = KnownPostItemType.VOTE
+        st: int
+        tt: str
+        ittpe: Optional[str] = None
+        its: list[dict]
+
+    @dataclass(kw_only=True)
+    class Video(Unknown):
+        t = KnownPostItemType.VIDEO
+        th: str
+
+    @dataclass(kw_only=True)
+    class File(Unknown):
+        t = KnownPostItemType.FILE
+        tt: str
+        c: int
+
+    @dataclass(kw_only=True)
+    class Footer(Unknown):
+        t = KnownPostItemType.FOOTER
+        st: PostFooterStyle
+        url: str
+
+
+@dataclass(kw_only=True)
+class PostAttachment(Attachment):
+    subtype: Optional[PostSubItemType] = None
+    os: list[PostItem.Unknown]
+
+
+@dataclass
+class VoteAttachment(PostAttachment):
+    voteId: int
+    title: str
+
+
+__all__ = [
+    "KnownPostItemType",
+    "PostItemType",
+    "KnownPostSubItemType",
+    "PostSubItemType",
+    "KnownPostFooterStyle",
+    "PostFooterStyle",
+    "PostItem",
+    "PostAttachment",
+    "VoteAttachment",
+]
diff --git a/matrix_appservice_kakaotalk/kt/types/chat/attachment/reply.py b/matrix_appservice_kakaotalk/kt/types/chat/attachment/reply.py
new file mode 100644
index 0000000..dbb9993
--- /dev/null
+++ b/matrix_appservice_kakaotalk/kt/types/chat/attachment/reply.py
@@ -0,0 +1,40 @@
+# matrix-appservice-kakaotalk - A Matrix-KakaoTalk puppeting bridge.
+# Copyright (C) 2022 Tulir Asokan, Andrew Ferrazzutti
+#
+# 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 typing import Optional
+
+from attr import dataclass
+
+from ...bson import Long
+from . import Attachment
+from ..chat_type import ChatType
+from .mention import MentionStruct
+
+
+@dataclass(kw_only=True)
+class ReplyAttachment(Attachment):
+    attach_only: bool
+    attach_type: int
+    src_linkId: Optional[Long] = None
+    src_logId: Long
+    src_mentions: list[MentionStruct]
+    src_message: str
+    src_type: ChatType
+    src_userId: Long
+
+
+__all__ = [
+    "ReplyAttachment",
+]
diff --git a/matrix_appservice_kakaotalk/kt/types/chat/chat.py b/matrix_appservice_kakaotalk/kt/types/chat/chat.py
index 0f454a4..62201ed 100644
--- a/matrix_appservice_kakaotalk/kt/types/chat/chat.py
+++ b/matrix_appservice_kakaotalk/kt/types/chat/chat.py
@@ -13,16 +13,30 @@
 #
 # 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 typing import Optional, Union
+from typing import Optional, Union, Type
 
 from attr import dataclass
 
-from mautrix.types import SerializableAttrs
+from mautrix.types import SerializableAttrs, JSON
 
 from ..bson import Long
 from ..user.channel_user import ChannelUser
-from ..attachment import Attachment
-from .chat_type import ChatType
+from .attachment import (
+    Attachment,
+    PhotoAttachment,
+    VideoAttachment,
+    ContactAttachment,
+    AudioAttachment,
+    EmoticonAttachment,
+    OpenScheduleAttachment,
+    VoteAttachment,
+    MapAttachment,
+    ProfileAttachment,
+    FileAttachment,
+    PostAttachment,
+    ReplyAttachment,
+)
+from .chat_type import ChatType, KnownChatType
 
 
 @dataclass
@@ -35,6 +49,36 @@ class Chat(ChatTypeComponent):
     attachment: Optional[Attachment] = None
     supplement: Optional[dict] = None
 
+    @classmethod
+    def deserialize(cls, data: JSON) -> "Chat":
+        if "attachment" in data:
+            attachment = _attachment_type_map.get(int(data["type"]), Attachment).deserialize(data["attachment"])
+            del data["attachment"]
+        else:
+            attachment = None
+        obj = super().deserialize(data)
+        obj.attachment = attachment
+        return obj
+
+# TODO More
+_attachment_type_map: dict[KnownChatType, Type[Attachment]] = {
+    KnownChatType.PHOTO: PhotoAttachment,
+    KnownChatType.VIDEO: VideoAttachment,
+    KnownChatType.CONTACT: ContactAttachment,
+    KnownChatType.AUDIO: AudioAttachment,
+    KnownChatType.DITEMEMOTICON: EmoticonAttachment,
+    KnownChatType.SCHEDULE: OpenScheduleAttachment,
+    KnownChatType.VOTE: VoteAttachment,
+    KnownChatType.MAP: MapAttachment,
+    KnownChatType.PROFILE: ProfileAttachment,
+    KnownChatType.FILE: FileAttachment,
+    KnownChatType.POST: PostAttachment,
+    KnownChatType.REPLY: ReplyAttachment,
+    KnownChatType.OPEN_SCHEDULE: OpenScheduleAttachment,
+    KnownChatType.OPEN_VOTE: VoteAttachment,
+    KnownChatType.OPEN_POST: PostAttachment,
+}
+
 
 @dataclass
 class TypedChat(Chat, ChatTypeComponent):
diff --git a/matrix_appservice_kakaotalk/portal.py b/matrix_appservice_kakaotalk/portal.py
index 249a756..e012fc2 100644
--- a/matrix_appservice_kakaotalk/portal.py
+++ b/matrix_appservice_kakaotalk/portal.py
@@ -15,7 +15,16 @@
 # along with this program.  If not, see <https://www.gnu.org/licenses/>.
 from __future__ import annotations
 
-from typing import TYPE_CHECKING, Any, AsyncGenerator, Pattern, cast
+from typing import (
+    TYPE_CHECKING,
+    Any,
+    AsyncGenerator,
+    Awaitable,
+    Callable,
+    Pattern,
+    cast,
+)
+from io import BytesIO
 import asyncio
 import re
 import time
@@ -24,9 +33,13 @@ from mautrix.appservice import IntentAPI
 from mautrix.bridge import BasePortal, NotificationDisabler, async_getter_lock
 from mautrix.errors import MatrixError
 from mautrix.types import (
+    AudioInfo,
     ContentURI,
+    EncryptedFile,
     EventID,
     EventType,
+    FileInfo,
+    ImageInfo,
     LocationMessageEventContent,
     MediaMessageEventContent,
     Membership,
@@ -35,7 +48,9 @@ from mautrix.types import (
     RoomID,
     TextMessageEventContent,
     UserID,
+    VideoInfo,
 )
+from mautrix.util import ffmpeg, magic, variation_selector
 from mautrix.util.message_send_checkpoint import MessageSendCheckpointStatus
 from mautrix.util.simple_lock import SimpleLock
 
@@ -50,7 +65,10 @@ from .formatter import kakaotalk_to_matrix, matrix_to_kakaotalk
 from .kt.types.bson import Long
 from .kt.types.channel.channel_info import ChannelInfo
 from .kt.types.channel.channel_type import KnownChannelType, ChannelType
-from .kt.types.chat.chat import Chatlog
+from .kt.types.chat import Chatlog, KnownChatType
+from .kt.types.chat.attachment import (
+    PhotoAttachment,
+)
 
 from .kt.client.types import UserInfoUnion, PortalChannelInfo, ChannelProps
 from .kt.client.errors import CommandException
@@ -158,6 +176,18 @@ class Portal(DBPortal, BasePortal):
         NotificationDisabler.puppet_cls = p.Puppet
         NotificationDisabler.config_enabled = cls.config["bridge.backfill.disable_notifications"]
 
+        # TODO More
+        cls._message_handler_type_map: dict[
+            KnownChatType,
+            Callable[[Portal, u.User, IntentAPI, Chatlog], Awaitable[list[EventID]]]
+        ] = {
+            KnownChatType.TEXT: cls._handle_remote_text,
+            KnownChatType.PHOTO: cls._handle_remote_photo,
+            #KnownChatType.VIDEO: cls._handle_remote_video,
+            #KnownChatType.AUDIO: cls._handle_remote_audio,
+            #KnownChatType.FILE: cls._handle_remote_file,
+        }
+
     # region DB conversion
 
     async def delete(self) -> None:
@@ -268,9 +298,8 @@ class Portal(DBPortal, BasePortal):
             await self.save()
         return info
 
-    """
     @classmethod
-    async def _reupload_kt_file(
+    async def _reupload_remote_file(
         cls,
         url: str,
         source: u.User,
@@ -278,20 +307,19 @@ class Portal(DBPortal, BasePortal):
         *,
         filename: str | None = None,
         encrypt: bool = False,
-        referer: str = "messenger_thread_photo",
         find_size: bool = False,
         convert_audio: bool = False,
     ) -> tuple[ContentURI, FileInfo | VideoInfo | AudioInfo | ImageInfo, EncryptedFile | None]:
         if not url:
             raise ValueError("URL not provided")
-        headers = {"referer": f"fbapp://{source.state.application.client_id}/{referer}"}
         sandbox = cls.config["bridge.sandbox_media_download"]
-        async with source.client.get(url, headers=headers, sandbox=sandbox) as resp:
+        # TODO Referer header?
+        async with source.client.get(url, sandbox=sandbox) as resp:
             length = int(resp.headers["Content-Length"])
             if length > cls.matrix.media_config.upload_size:
                 raise ValueError("File not available: too large")
             data = await resp.read()
-        mime = magic.from_buffer(data, mime=True)
+        mime = magic.mimetype(data)
         if convert_audio and mime != "audio/ogg":
             data = await ffmpeg.convert_bytes(
                 data, ".ogg", output_args=("-c:a", "libopus"), input_mime=mime
@@ -312,7 +340,6 @@ class Portal(DBPortal, BasePortal):
         if decryption_info:
             decryption_info.url = url
         return url, info, decryption_info
-    """
 
     async def _update_name(self, name: str) -> bool:
         if not name:
@@ -859,10 +886,9 @@ class Portal(DBPortal, BasePortal):
         source: u.User,
         sender: p.Puppet,
         message: Chatlog,
-        reply_to: Chatlog | None = None,
     ) -> None:
         try:
-            await self._handle_remote_message(source, sender, message, reply_to)
+            await self._handle_remote_message(source, sender, message)
         except Exception:
             self.log.exception(
                 "Error handling KakaoTalk message %s",
@@ -874,7 +900,6 @@ class Portal(DBPortal, BasePortal):
         source: u.User,
         sender: p.Puppet,
         message: Chatlog,
-        reply_to: Chatlog | None = None,
     ) -> None:
         self.log.debug(f"Handling KakaoTalk event {message.logId}")
         if not self.mxid:
@@ -896,25 +921,59 @@ class Portal(DBPortal, BasePortal):
             await intent.ensure_joined(self.mxid)
             self._backfill_leave.add(intent)
 
-        if message.attachment:
-            self.log.info("TODO: _handle_remote_message attachments")
-        if message.supplement:
-            self.log.info("TODO: _handle_remote_message supplements")
-        if message.text:
-            content = await kakaotalk_to_matrix(message.text)
-            event_id = await self._send_message(intent, content, timestamp=message.sendAt)
-            await DBMessage(
-                mxid=event_id,
-                mx_room=self.mxid,
-                ktid=message.logId,
-                index=0,
-                kt_chat=self.ktid,
-                kt_receiver=self.kt_receiver,
-                timestamp=message.sendAt,
-            ).insert()
-            await self._send_delivery_receipt(event_id)
-        else:
+        event_ids = []
+        handler = self._message_handler_type_map.get(message.type)
+        if not handler:
+            self.log.warning(f"No handler for message type {message.type}, falling back to text")
+            handler = Portal._handle_remote_text
+        event_ids += await handler(self, source, intent, message)
+        if not event_ids:
             self.log.warning(f"Unhandled KakaoTalk message {message.logId}")
+            return
+        event_ids = [event_id for event_id in event_ids if event_id]
+        self.log.debug(f"Handled KakaoTalk message {message.logId} -> {event_ids}")
+        await DBMessage.bulk_create(
+            ktid=message.logId,
+            kt_chat=self.ktid,
+            kt_receiver=self.kt_receiver,
+            mx_room=self.mxid,
+            timestamp=message.sendAt,
+            event_ids=event_ids,
+        )
+        await self._send_delivery_receipt(event_ids[-1])
+
+    async def _handle_remote_text(self, source: u.User, intent: IntentAPI, message: Chatlog) -> list[EventID]:
+        # TODO Handle mentions properly
+        content = await kakaotalk_to_matrix(message.text)
+        # TODO Replies
+        return [await self._send_message(intent, content, timestamp=message.sendAt)]
+
+    async def _handle_remote_photo(self, source: u.User, intent: IntentAPI, message: Chatlog) -> list[EventID]:
+        assert message.attachment
+        assert message.attachment.url or message.attachment.urls
+        url = message.attachment.url or message.attachment.urls[0]
+        assert isinstance(message.attachment, PhotoAttachment)
+        info = ImageInfo(
+            width=message.attachment.w,
+            height=message.attachment.h,
+        )
+        # TODO Animated images?
+        mxc, additional_info, decryption_info = await self._reupload_remote_file(
+            url,
+            source,
+            intent,
+            encrypt=self.encrypted,
+            find_size=False,
+        )
+        info.size = additional_info.size
+        info.mimetype = additional_info.mimetype
+        content = MediaMessageEventContent(
+            url=mxc, file=decryption_info, msgtype=MessageType.IMAGE, body=message.text, info=info
+        )
+        if not content:
+            return []
+        # TODO Replies
+        return [await self._send_message(intent, content, timestamp=message.sendAt)]
 
     # TODO Many more remote handlers
 
diff --git a/matrix_appservice_kakaotalk/user.py b/matrix_appservice_kakaotalk/user.py
index feca078..0003769 100644
--- a/matrix_appservice_kakaotalk/user.py
+++ b/matrix_appservice_kakaotalk/user.py
@@ -606,7 +606,6 @@ class User(DBUser, BaseUser):
         await portal.backfill_lock.wait(evt.logId)
         if not puppet.name:
             portal.schedule_resync(self, puppet)
-        # TODO reply_to
         await portal.handle_remote_message(self, puppet, evt)
 
     # TODO Many more handlers