diff --git a/m2d/actions/send-event.js b/m2d/actions/send-event.js
index 18a1e0f..e870675 100644
--- a/m2d/actions/send-event.js
+++ b/m2d/actions/send-event.js
@@ -1,6 +1,7 @@
 // @ts-check
 
 const assert = require("assert").strict
+const Ty = require("../../types")
 const DiscordTypes = require("discord-api-types/v10")
 const passthrough = require("../../passthrough")
 const {sync, discord, db} = passthrough
@@ -12,9 +13,30 @@ const eventToMessage = sync.require("../converters/event-to-message")
 /** @type {import("../../matrix/api")}) */
 const api = sync.require("../../matrix/api")
 
-/** @param {import("../../types").Event.Outer<any>} event */
+/**
+ * @param {DiscordTypes.RESTPostAPIWebhookWithTokenJSONBody & {pendingFiles?: {name: string, url: string}[]}} message
+ * @returns {Promise<DiscordTypes.RESTPostAPIWebhookWithTokenJSONBody & {files?: {name: string, file: Buffer}[]}>}
+ */
+async function resolvePendingFiles(message) {
+	if (!message.pendingFiles) return message
+	const files = await Promise.all(message.pendingFiles.map(async p => {
+		const file = await fetch(p.url).then(res => res.arrayBuffer()).then(x => Buffer.from(x))
+		return {
+			name: p.name,
+			file
+		}
+	}))
+	const newMessage = {
+		...message,
+		files
+	}
+	delete newMessage.pendingFiles
+	return newMessage
+}
+
+/** @param {Ty.Event.M_Outer_M_Room_Message | Ty.Event.M_Outer_M_Room_Message_File | Ty.Event.M_Outer_M_Sticker} event */
 async function sendEvent(event) {
-	// TODO: we just assume the bridge has already been created
+	// TODO: we just assume the bridge has already been created, is that really ok?
 	const row = db.prepare("SELECT channel_id, thread_parent FROM channel_room WHERE room_id = ?").get(event.room_id)
 	let channelID = row.channel_id
 	let threadID = undefined
@@ -29,7 +51,15 @@ async function sendEvent(event) {
 
 	// no need to sync the matrix member to the other side. but if I did need to, this is where I'd do it
 
-	const {messagesToEdit, messagesToSend, messagesToDelete} = await eventToMessage.eventToMessage(event, guild, {api})
+	let {messagesToEdit, messagesToSend, messagesToDelete} = await eventToMessage.eventToMessage(event, guild, {api})
+
+	messagesToEdit = await Promise.all(messagesToEdit.map(async e => {
+		e.message = await resolvePendingFiles(e.message)
+		return e
+	}))
+	messagesToSend = await Promise.all(messagesToSend.map(message => {
+		return resolvePendingFiles(message)
+	}))
 
 	let eventPart = 0 // 0 is primary, 1 is supporting
 
@@ -48,7 +78,7 @@ async function sendEvent(event) {
 	for (const message of messagesToSend) {
 		const messageResponse = await channelWebhook.sendMessageWithWebhook(channelID, message, threadID)
 		db.prepare("REPLACE INTO message_channel (message_id, channel_id) VALUES (?, ?)").run(messageResponse.id, channelID)
-		db.prepare("INSERT INTO event_message (event_id, event_type, event_subtype, message_id, part, source) VALUES (?, ?, ?, ?, ?, 0)").run(event.event_id, event.type, event.content.msgtype || null, messageResponse.id, eventPart) // source 0 = matrix
+		db.prepare("INSERT INTO event_message (event_id, event_type, event_subtype, message_id, part, source) VALUES (?, ?, ?, ?, ?, 0)").run(event.event_id, event.type, event.content["msgtype"] || null, messageResponse.id, eventPart) // source 0 = matrix
 
 		eventPart = 1
 		messageResponses.push(messageResponse)
diff --git a/m2d/converters/event-to-message.js b/m2d/converters/event-to-message.js
index deb7b9f..a8a5b65 100644
--- a/m2d/converters/event-to-message.js
+++ b/m2d/converters/event-to-message.js
@@ -4,6 +4,7 @@ const Ty = require("../../types")
 const DiscordTypes = require("discord-api-types/v10")
 const chunk = require("chunk-text")
 const TurndownService = require("turndown")
+const assert = require("assert").strict
 
 const passthrough = require("../../passthrough")
 const { sync, db, discord } = passthrough
@@ -124,7 +125,7 @@ async function getMemberFromCacheOrHomeserver(roomID, mxid, api) {
 }
 
 /**
- * @param {Ty.Event.Outer<Ty.Event.M_Room_Message>} event
+ * @param {Ty.Event.M_Outer_M_Room_Message | Ty.Event.M_Outer_M_Room_Message_File | Ty.Event.M_Outer_M_Sticker} event
  * @param {import("discord-api-types/v10").APIGuild} guild
  * @param {{api: import("../../matrix/api")}} di simple-as-nails dependency injection for the matrix API
  */
@@ -143,12 +144,15 @@ async function eventToMessage(event, guild, di) {
 	// Try to extract an accurate display name and avatar URL from the member event
 	const member = await getMemberFromCacheOrHomeserver(event.room_id, event.sender, di?.api)
 	if (member.displayname) displayName = member.displayname
-	if (member.avatar_url) avatarURL = utils.getPublicUrlForMxc(member.avatar_url)
+	if (member.avatar_url) avatarURL = utils.getPublicUrlForMxc(member.avatar_url) || undefined
 
 	let content = event.content.body // ultimate fallback
+	const attachments = []
+	/** @type {{name: string, url: string}[]} */
+	const pendingFiles = []
 
 	// Convert content depending on what the message is
-	if (event.content.msgtype === "m.text" || event.content.msgtype === "m.emote") {
+	if (event.type === "m.room.message" && (event.content.msgtype === "m.text" || event.content.msgtype === "m.emote")) {
 		// Handling edits. If the edit was an edit of a reply, edits do not include the reply reference, so we need to fetch up to 2 more events.
 		// this event ---is an edit of--> original event ---is a reply to--> past event
 		await (async () => {
@@ -261,7 +265,7 @@ async function eventToMessage(event, guild, di) {
 			// @ts-ignore bad type from turndown
 			content = turndownService.turndown(input)
 
-			// It's optimised for commonmark, we need to replace the space-space-newline with just newline
+			// It's designed for commonmark, we need to replace the space-space-newline with just newline
 			content = content.replace(/  \n/g, "\n")
 		} else {
 			// Looks like we're using the plaintext body!
@@ -274,6 +278,23 @@ async function eventToMessage(event, guild, di) {
 			// Markdown needs to be escaped
 			content = content.replace(/([*_~`#])/g, `\\$1`)
 		}
+	} else if (event.type === "m.room.message" && (event.content.msgtype === "m.file" || event.content.msgtype === "m.video" || event.content.msgtype === "m.audio" || event.content.msgtype === "m.image")) {
+		content = ""
+		const filename = event.content.body
+		const url = utils.getPublicUrlForMxc(event.content.url)
+		assert(url)
+		attachments.push({id: "0", filename})
+		pendingFiles.push({name: filename, url})
+	} else if (event.type === "m.sticker") {
+		content = ""
+		let filename = event.content.body
+		if (event.type === "m.sticker" && event.content.info.mimetype.includes("/")) {
+			filename += "." + event.content.info.mimetype.split("/")[1]
+		}
+		const url = utils.getPublicUrlForMxc(event.content.url)
+		assert(url)
+		attachments.push({id: "0", filename})
+		pendingFiles.push({name: filename, url})
 	}
 
 	content = replyLine + content
@@ -286,6 +307,19 @@ async function eventToMessage(event, guild, di) {
 		avatar_url: avatarURL
 	})))
 
+	if (attachments.length) {
+		// If content is empty (should be the case when uploading a file) then chunk-text will create 0 messages.
+		// There needs to be a message to add attachments to.
+		if (!messages.length) messages.push({
+			content,
+			username: displayName,
+			avatar_url: avatarURL
+		})
+		messages[0].attachments = attachments
+		// @ts-ignore these will be converted to real files when the message is about to be sent
+		messages[0].pendingFiles = pendingFiles
+	}
+
 	const messagesToEdit = []
 	const messagesToSend = []
 	for (let i = 0; i < messages.length; i++) {
diff --git a/m2d/converters/event-to-message.test.js b/m2d/converters/event-to-message.test.js
index 411d97c..5a83f0c 100644
--- a/m2d/converters/event-to-message.test.js
+++ b/m2d/converters/event-to-message.test.js
@@ -1110,3 +1110,107 @@ test("event2message: skips caching the member if the member does not exist, some
 	t.deepEqual(db.prepare("SELECT avatar_url, displayname, mxid FROM member_cache WHERE room_id = '!not_real:cadence.moe'").all(), [])
 	t.equal(called, 1, "getStateEvent should be called once")
 })
+
+test("event2message: text attachments work", async t => {
+	t.deepEqual(
+		await eventToMessage({
+			type: "m.room.message",
+			content: {
+				body: "chiki-powerups.txt",
+				info: {
+					size: 971,
+					mimetype: "text/plain"
+				},
+				msgtype: "m.file",
+				url: "mxc://cadence.moe/zyThGlYQxvlvBVbVgKDDbiHH"
+			},
+			sender: "@cadence:cadence.moe",
+			event_id: "$c2WVyP6KcfAqh5imOa8e0xzt2C8JTR-cWbEd3GargEQ",
+			room_id: "!PnyBKvUBOhjuCucEfk:cadence.moe"
+		}),
+		{
+			messagesToDelete: [],
+			messagesToEdit: [],
+			messagesToSend: [{
+				username: "cadence [they]",
+				content: "",
+				avatar_url: "https://matrix.cadence.moe/_matrix/media/r0/download/cadence.moe/azCAhThKTojXSZJRoWwZmhvU",
+				attachments: [{id: "0", filename: "chiki-powerups.txt"}],
+				pendingFiles: [{name: "chiki-powerups.txt", url: "https://matrix.cadence.moe/_matrix/media/r0/download/cadence.moe/zyThGlYQxvlvBVbVgKDDbiHH"}]
+			}]
+		}
+	)
+})
+
+test("event2message: image attachments work", async t => {
+	t.deepEqual(
+		await eventToMessage({
+			type: "m.room.message",
+			sender: "@cadence:cadence.moe",
+			content: {
+				body: "cool cat.png",
+				info: {
+					size: 43170,
+					mimetype: "image/png",
+					w: 480,
+					h: 480,
+					"xyz.amorgan.blurhash": "URTHsVaTpdj2eKZgkkkXp{pHl7feo@lSl9Z$"
+				},
+				msgtype: "m.image",
+				url: "mxc://cadence.moe/IvxVJFLEuksCNnbojdSIeEvn"
+			},
+			event_id: "$CXQy3Wmg1A-gL_xAesC1HQcQTEXwICLdSwwUx55FBTI",
+			room_id: "!PnyBKvUBOhjuCucEfk:cadence.moe"
+		}),
+		{
+			messagesToDelete: [],
+			messagesToEdit: [],
+			messagesToSend: [{
+				username: "cadence [they]",
+				content: "",
+				avatar_url: "https://matrix.cadence.moe/_matrix/media/r0/download/cadence.moe/azCAhThKTojXSZJRoWwZmhvU",
+				attachments: [{id: "0", filename: "cool cat.png"}],
+				pendingFiles: [{name: "cool cat.png", url: "https://matrix.cadence.moe/_matrix/media/r0/download/cadence.moe/IvxVJFLEuksCNnbojdSIeEvn"}]
+			}]
+		}
+	)
+})
+
+test("event2message: stickers work", async t => {
+	t.deepEqual(
+		await eventToMessage({
+			type: "m.sticker",
+			sender: "@cadence:cadence.moe",
+			content: {
+				body: "get_real2",
+				url: "mxc://cadence.moe/NyMXQFAAdniImbHzsygScbmN",
+				info: {
+					w: 320,
+					h: 298,
+					mimetype: "image/gif",
+					size: 331394,
+					thumbnail_info: {
+						w: 320,
+						h: 298,
+						mimetype: "image/gif",
+						size: 331394
+					},
+					thumbnail_url: "mxc://cadence.moe/NyMXQFAAdniImbHzsygScbmN"
+				}
+			},
+			event_id: "$PdI-KjdQ8Z_Tb4x9_7wKRPZCsrrXym4BXtbAPekypuM",
+			room_id: "!PnyBKvUBOhjuCucEfk:cadence.moe"
+		}),
+		{
+			messagesToDelete: [],
+			messagesToEdit: [],
+			messagesToSend: [{
+				username: "cadence [they]",
+				content: "",
+				avatar_url: "https://matrix.cadence.moe/_matrix/media/r0/download/cadence.moe/azCAhThKTojXSZJRoWwZmhvU",
+				attachments: [{id: "0", filename: "get_real2.gif"}],
+				pendingFiles: [{name: "get_real2.gif", url: "https://matrix.cadence.moe/_matrix/media/r0/download/cadence.moe/NyMXQFAAdniImbHzsygScbmN"}]
+			}]
+		}
+	)
+})
diff --git a/m2d/event-dispatcher.js b/m2d/event-dispatcher.js
index 6adacf7..026b067 100644
--- a/m2d/event-dispatcher.js
+++ b/m2d/event-dispatcher.js
@@ -54,7 +54,16 @@ function guard(type, fn) {
 
 sync.addTemporaryListener(as, "type:m.room.message", guard("m.room.message",
 /**
- * @param {Ty.Event.Outer<Ty.Event.M_Room_Message>} event it is a m.room.message because that's what this listener is filtering for
+ * @param {Ty.Event.M_Outer_M_Room_Message | Ty.Event.M_Outer_M_Room_Message_File} event it is a m.room.message because that's what this listener is filtering for
+ */
+async event => {
+	if (utils.eventSenderIsFromDiscord(event.sender)) return
+	const messageResponses = await sendEvent.sendEvent(event)
+}))
+
+sync.addTemporaryListener(as, "type:m.sticker", guard("m.sticker",
+/**
+ * @param {Ty.Event.M_Outer_M_Sticker} event it is a m.sticker because that's what this listener is filtering for
  */
 async event => {
 	if (utils.eventSenderIsFromDiscord(event.sender)) return
diff --git a/types.d.ts b/types.d.ts
index dcde3ad..b74172b 100644
--- a/types.d.ts
+++ b/types.d.ts
@@ -80,6 +80,39 @@ export namespace Event {
 		}
 	}
 
+	export type M_Outer_M_Room_Message = Outer<M_Room_Message> & {type: "m.room.message"}
+
+	export type M_Room_Message_File = {
+		msgtype: "m.file" | "m.image" | "m.video" | "m.audio"
+		body: string
+		url: string
+		info?: any
+		"m.relates_to"?: {
+			"m.in_reply_to": {
+				event_id: string
+			}
+			rel_type?: "m.replace"
+			event_id?: string
+		}
+	}
+
+	export type M_Outer_M_Room_Message_File = Outer<M_Room_Message_File> & {type: "m.room.message"}
+
+	export type M_Sticker = {
+		body: string
+		url: string
+		info: {
+			mimetype: string
+			w?: number
+			h?: number
+			size?: number
+			thumbnail_info?: any
+			thumbnail_url?: string
+		}
+	}
+
+	export type M_Outer_M_Sticker = Outer<M_Sticker> & {type: "m.sticker"}
+
 	export type M_Room_Member = {
 		membership: string
 		displayname?: string