diff --git a/puppet/src/contentscript.js b/puppet/src/contentscript.js
index 66ec9e4..207c7cf 100644
--- a/puppet/src/contentscript.js
+++ b/puppet/src/contentscript.js
@@ -95,6 +95,7 @@ class MautrixController {
 		this.pinAppearObserver = null
 		this.ownID = null
 
+		this.ownMsgPromise = Promise.resolve(-1)
 		this._promiseOwnMsgReset()
 	}
 
@@ -474,13 +475,20 @@ class MautrixController {
 		}, timeoutLimitMillis)
 	}
 
+	/**
+	 * Check if we're waiting for a Matrix-sent message to resolve.
+	 */
+	_isWaitingForOwnMessage() {
+		return !!this.promiseOwnMsgResolve
+	}
+
 	/**
 	 * Wait for a user-sent message to finish getting sent.
 	 *
 	 * @return {Promise<number>} - The ID of the sent message.
 	 */
 	async waitForOwnMessage() {
-		return this.ownMsgPromise ? await this.ownMsgPromise : -1
+		return await this.ownMsgPromise
 	}
 
 	/**
@@ -867,7 +875,7 @@ class MautrixController {
 	addChatListObserver() {
 		this.removeChatListObserver()
 		this.chatListObserver = new MutationObserver(async (mutations) => {
-			if (this.ownMsgPromise) {
+			if (this._isWaitingForOwnMessage()) {
 				// Wait for pending sent messages to be resolved before responding to mutations
 				try {
 					await this.ownMsgPromise
@@ -1213,8 +1221,7 @@ class MautrixController {
 	}
 
 	_observeOwnMessage(ownMsg) {
-		if (!this.ownMsgPromise) {
-			// Not waiting for a pending sent message
+		if (!this._isWaitingForOwnMessage()) {
 			return null
 		}
 
@@ -1299,7 +1306,6 @@ class MautrixController {
 	}
 
 	_promiseOwnMsgReset() {
-		this.ownMsgPromise = null
 		this.promiseOwnMsgSuccessSelector = null
 		this.promiseOwnMsgFailureSelector = null
 		this.promiseOwnMsgResolve = null
diff --git a/puppet/src/puppet.js b/puppet/src/puppet.js
index 71bca9d..c382e69 100644
--- a/puppet/src/puppet.js
+++ b/puppet/src/puppet.js
@@ -790,7 +790,18 @@ export default class MessagesPuppeteer {
 			// Setting its innerText directly works fine though...
 			await input.click()
 			await input.evaluate((e, text) => e.innerText = text, text)
-			await input.press("Enter")
+			while (true) {
+				await input.press("Enter")
+				try {
+					await this.page.waitForFunction(
+						e => e.innerText == "",
+						{timeout: 500},
+						input)
+					break
+				} catch (e) {
+					this.error(`Failed to press Enter when sending message, try again (${e})`)
+				}
+			}
 		})
 
 		return await this._waitForSentMessage(chatID)