diff --git a/src/d2m/actions/register-user.js b/src/d2m/actions/register-user.js
index b914d41..94daa34 100644
--- a/src/d2m/actions/register-user.js
+++ b/src/d2m/actions/register-user.js
@@ -208,6 +208,34 @@ async function syncUser(user, member, channel, guild, roomID) {
 	return mxid
 }
 
+/**
+ * Sync profile data for a webhook user. The _ooye_webhook name will always be reused.
+ * 1. Join the sim to the room if needed
+ * 2. Make an object of what the new room member state content would be, including uploading the profile picture if it hasn't been done before
+ * 4. Compare against the previously known state content, which is helpfully stored in the database
+ * 5. If the state content has changed, send it to Matrix and update it in the database for next time
+ * @param {DiscordTypes.APIUser} user
+ * @param {DiscordTypes.APIGuildChannel} channel
+ * @param {DiscordTypes.APIGuild} guild
+ * @param {string} roomID
+ * @returns {Promise<string>} mxid of the updated sim
+ */
+async function syncWebhook(user, channel, guild, roomID) {
+	const mxid = await ensureSimJoined(user, roomID)
+	// @ts-ignore
+	const content = await memberToStateContent(user, {}, guild.id)
+	const currentHash = _hashProfileContent(content, 0)
+	const existingHash = select("sim_member", "hashed_profile_content", {room_id: roomID, mxid}).safeIntegers().pluck().get()
+	// only do the actual sync if the hash has changed since we last looked
+	if (existingHash !== currentHash) {
+		// Update room member state
+		await api.sendState(roomID, "m.room.member", mxid, content, mxid)
+		// Update cached hash
+		db.prepare("UPDATE sim_member SET hashed_profile_content = ? WHERE room_id = ? AND mxid = ?").run(currentHash, roomID, mxid)
+	}
+	return mxid
+}
+
 /**
  * @param {string} roomID
  */
@@ -244,4 +272,5 @@ module.exports._hashProfileContent = _hashProfileContent
 module.exports.ensureSim = ensureSim
 module.exports.ensureSimJoined = ensureSimJoined
 module.exports.syncUser = syncUser
+module.exports.syncWebhook = syncWebhook
 module.exports.syncAllUsersInRoom = syncAllUsersInRoom
diff --git a/src/d2m/actions/send-message.js b/src/d2m/actions/send-message.js
index 6d100d4..ac3378c 100644
--- a/src/d2m/actions/send-message.js
+++ b/src/d2m/actions/send-message.js
@@ -28,20 +28,20 @@ async function sendMessage(message, channel, guild, row) {
 	const roomID = await createRoom.ensureRoom(message.channel_id)
 
 	let senderMxid = null
-	if (!dUtils.isWebhookMessage(message)) {
-		if (message.author.id === discord.application.id) {
-			// no need to sync the bot's own user
-		} else if (message.member) { // available on a gateway message create event
-			senderMxid = await registerUser.syncUser(message.author, message.member, channel, guild, roomID)
-		} else { // well, good enough...
-			senderMxid = await registerUser.ensureSimJoined(message.author, roomID)
-		}
-	} else if (row && row.speedbump_webhook_id === message.webhook_id) {
+	if (row && row.speedbump_webhook_id === message.webhook_id) {
 		// Handle the PluralKit public instance
 		if (row.speedbump_id === "466378653216014359") {
 			const pkMessage = await registerPkUser.fetchMessage(message.id)
 			senderMxid = await registerPkUser.syncUser(message.author, pkMessage, roomID)
 		}
+	} else if (message.author.id === discord.application.id) {
+		// no need to sync the bot's own user
+	} else if (dUtils.isWebhookMessage(message)) {
+		senderMxid = await registerUser.syncWebhook(message.author, channel, guild, roomID)
+	} else if (message.member) { // available on a gateway message create event
+		senderMxid = await registerUser.syncUser(message.author, message.member, channel, guild, roomID)
+	} else { // well, good enough...
+		senderMxid = await registerUser.ensureSimJoined(message.author, roomID)
 	}
 
 	const events = await messageToEvent.messageToEvent(message, guild, {}, {api})
diff --git a/src/d2m/converters/user-to-mxid.js b/src/d2m/converters/user-to-mxid.js
index a619b36..3d7d834 100644
--- a/src/d2m/converters/user-to-mxid.js
+++ b/src/d2m/converters/user-to-mxid.js
@@ -60,7 +60,7 @@ function* generateLocalpartAlternatives(preferences) {
  */
 function userToSimName(user) {
 	if (!SPECIAL_USER_MAPPINGS.has(user.id)) { // skip this check for known special users
-		assert.notEqual(user.discriminator, "0000", `cannot create user for a webhook: ${JSON.stringify(user)}`)
+		if (user.discriminator === "0000") return "webhook"
 	}
 
 	// 1. Is sim user already registered?