diff --git a/d2m/discord-command-handler.js b/d2m/discord-command-handler.js
index 9f96c18f..1bd52c8a 100644
--- a/d2m/discord-command-handler.js
+++ b/d2m/discord-command-handler.js
@@ -6,15 +6,48 @@ const DiscordTypes = require("discord-api-types/v10")
 const {discord, sync, db} = require("../passthrough")
 /** @type {import("../matrix/api")}) */
 const api = sync.require("../matrix/api")
+/** @type {import("../matrix/file")} */
+const file = sync.require("../matrix/file")
 
-const prefix = "/"
+const PREFIX = "//"
+
+let buttons = []
+
+/**
+ * @param {string} channelID where to add the button
+ * @param {string} messageID where to add the button
+ * @param {string} emoji emoji to add as a button
+ * @param {string} userID only listen for responses from this user
+ * @returns {Promise<import("discord-api-types/v10").GatewayMessageReactionAddDispatchData>}
+ */
+async function addButton(channelID, messageID, emoji, userID) {
+	await discord.snow.channel.createReaction(channelID, messageID, emoji)
+	return new Promise(resolve => {
+		buttons.push({channelID, messageID, userID, resolve, created: Date.now()})
+	})
+}
+
+// Clear out old buttons every so often to free memory
+setInterval(() => {
+	const now = Date.now()
+	buttons = buttons.filter(b => now - b.created < 2*60*60*1000)
+}, 10*60*1000)
+
+/** @param {import("discord-api-types/v10").GatewayMessageReactionAddDispatchData} data */
+function onReactionAdd(data) {
+	const button = buttons.find(b => b.channelID === data.channel_id && b.messageID === data.message_id && b.userID === data.user_id)
+	if (button) {
+		buttons = buttons.filter(b => b !== button) // remove button data so it can't be clicked again
+		button.resolve(data)
+	}
+}
 
 /**
  * @callback CommandExecute
  * @param {DiscordTypes.GatewayMessageCreateDispatchData} message
  * @param {DiscordTypes.APIGuildTextChannel} channel
  * @param {DiscordTypes.APIGuild} guild
- * @param {any} [ctx]
+ * @param {Partial<DiscordTypes.RESTPostAPIChannelMessageJSONBody>} [ctx]
  */
 
 /**
@@ -42,24 +75,51 @@ const commands = [{
 	aliases: ["icon", "avatar", "roomicon", "roomavatar", "channelicon", "channelavatar"],
 	execute: replyctx(
 		async (message, channel, guild, ctx) => {
+			// Guard
 			const roomID = db.prepare("SELECT room_id FROM channel_room WHERE channel_id = ?").pluck().get(channel.id)
 			if (!roomID) return discord.snow.channel.createMessage(channel.id, {
 				...ctx,
 				content: "This channel isn't bridged to the other side."
 			})
+
+			// Current avatar
 			const avatarEvent = await api.getStateEvent(roomID, "m.room.avatar", "")
-			const avatarURL = avatarEvent?.url
-			return discord.snow.channel.createMessage(channel.id, {
+			const avatarURLParts = avatarEvent?.url.match(/^mxc:\/\/([^/]+)\/(\w+)$/)
+			let currentAvatarMessage =
+				( avatarURLParts ? `Current room-specific avatar: https://matrix.cadence.moe/_matrix/media/r0/download/${avatarURLParts[1]}/${avatarURLParts[2]}`
+				: "No avatar. Now's your time to strike. Use `//icon` again with a link or upload to set the room-specific avatar.")
+
+			// Next potential avatar
+			const nextAvatarURL = message.attachments.find(a => a.content_type?.startsWith("image/"))?.url || message.content.match(/https?:\/\/[^ ]+\.[^ ]+\.(?:png|jpg|jpeg|webp)\b/)?.[0]
+			let nextAvatarMessage =
+				( nextAvatarURL ? `\nYou want to set it to: ${nextAvatarURL}\nHit ✅ to make it happen.`
+				: "")
+
+			const sent = await discord.snow.channel.createMessage(channel.id, {
 				...ctx,
-				content: `Current room avatar: ${avatarURL}`
+				content: currentAvatarMessage + nextAvatarMessage
 			})
+
+			if (nextAvatarURL) {
+				addButton(channel.id, sent.id, "✅", message.author.id).then(async data => {
+					const mxcUrl = await file.uploadDiscordFileToMxc(nextAvatarURL)
+					await api.sendState(roomID, "m.room.avatar", "", {
+						url: mxcUrl
+					})
+					db.prepare("UPDATE channel_room SET custom_avatar = ? WHERE channel_id = ?").run(mxcUrl, channel.id)
+					await discord.snow.channel.createMessage(channel.id, {
+						...ctx,
+						content: "Your creation is unleashed. Any complaints will be redirected to Grelbo."
+					})
+				})
+			}
 		}
 	)
 }, {
 	aliases: ["invite"],
 	execute: replyctx(
 		async (message, channel, guild, ctx) => {
-			discord.snow.channel.createMessage(channel.id, {
+			return discord.snow.channel.createMessage(channel.id, {
 				...ctx,
 				content: "This command isn't implemented yet."
 			})
@@ -69,8 +129,8 @@ const commands = [{
 
 /** @type {CommandExecute} */
 async function execute(message, channel, guild) {
-	if (!message.content.startsWith(prefix)) return
-	const words = message.content.split(" ")
+	if (!message.content.startsWith(PREFIX)) return
+	const words = message.content.slice(PREFIX.length).split(" ")
 	const commandName = words[0]
 	const command = commands.find(c => c.aliases.includes(commandName))
 	if (!command) return
@@ -79,3 +139,4 @@ async function execute(message, channel, guild) {
 }
 
 module.exports.execute = execute
+module.exports.onReactionAdd = onReactionAdd
diff --git a/d2m/event-dispatcher.js b/d2m/event-dispatcher.js
index 91a7cba2..bf9bbd23 100644
--- a/d2m/event-dispatcher.js
+++ b/d2m/event-dispatcher.js
@@ -197,6 +197,7 @@ module.exports = {
 	 */
 	async onReactionAdd(client, data) {
 		if (data.user_id === client.user.id) return // m2d reactions are added by the discord bot user - do not reflect them back to matrix.
+		discordCommandHandler.onReactionAdd(data)
 		if (data.emoji.id !== null) return // TODO: image emoji reactions
 		await addReaction.addReaction(data)
 	},