diff --git a/client/js/upload.js b/client/js/upload.js
index 3b2e164c..33d4e154 100644
--- a/client/js/upload.js
+++ b/client/js/upload.js
@@ -9,6 +9,7 @@ class Uploader {
 	init() {
 		this.xhr = null;
 		this.fileQueue = [];
+		this.tokenKeepAlive = null;
 
 		document.addEventListener("dragenter", (e) => this.dragEnter(e));
 		document.addEventListener("dragover", (e) => this.dragOver(e));
@@ -131,6 +132,12 @@ class Uploader {
 	uploadNextFileInQueue(token) {
 		const file = this.fileQueue.shift();
 
+		// Tell the server that we are still upload to this token
+		// so it does not become invalidated and fail the upload.
+		// This issue only happens if The Lounge is proxied through other software
+		// as it may buffer the upload before the upload request will be processed by The Lounge.
+		this.tokenKeepAlive = setInterval(() => socket.emit("upload:ping", token), 40 * 1000);
+
 		if (
 			store.state.settings.uploadCanvas &&
 			file.type.startsWith("image/") &&
@@ -219,6 +226,11 @@ class Uploader {
 	handleResponse(response) {
 		this.setProgress(0);
 
+		if (this.tokenKeepAlive) {
+			clearInterval(this.tokenKeepAlive);
+			this.tokenKeepAlive = null;
+		}
+
 		if (response.error) {
 			store.commit("currentUserVisibleError", response.error);
 			return;
diff --git a/src/plugins/uploader.js b/src/plugins/uploader.js
index dde02e4a..c365f776 100644
--- a/src/plugins/uploader.js
+++ b/src/plugins/uploader.js
@@ -11,7 +11,9 @@ const crypto = require("crypto");
 const isUtf8 = require("is-utf8");
 const log = require("../log");
 
-const whitelist = [
+// List of allowed mime types that can be rendered in browser
+// without forcing it to be downloaded
+const inlineContentDispositionTypes = [
 	"application/ogg",
 	"audio/midi",
 	"audio/mpeg",
@@ -35,17 +37,33 @@ class Uploader {
 		socket.on("upload:auth", () => {
 			const token = uuidv4();
 
-			uploadTokens.set(token, true);
-
 			socket.emit("upload:auth", token);
 
 			// Invalidate the token in one minute
-			setTimeout(() => uploadTokens.delete(token), 60 * 1000);
+			const timeout = Uploader.createTokenTimeout(token);
+
+			uploadTokens.set(token, timeout);
+		});
+
+		socket.on("upload:ping", (token) => {
+			if (typeof token !== "string") {
+				return;
+			}
+
+			let timeout = uploadTokens.get(token);
+
+			if (!timeout) {
+				return;
+			}
+
+			clearTimeout(timeout);
+			timeout = Uploader.createTokenTimeout(token);
+			uploadTokens.set(token, timeout);
 		});
 	}
 
-	static isValidType(mimeType) {
-		return whitelist.includes(mimeType);
+	static createTokenTimeout(token) {
+		return setTimeout(() => uploadTokens.delete(token), 60 * 1000);
 	}
 
 	static router(express) {
@@ -72,8 +90,10 @@ class Uploader {
 			return res.status(404).send("Not found");
 		}
 
-		// Force a download in the browser if it's not a whitelisted type (binary or otherwise unknown)
-		const contentDisposition = Uploader.isValidType(detectedMimeType) ? "inline" : "attachment";
+		// Force a download in the browser if it's not an allowed type (binary or otherwise unknown)
+		const contentDisposition = inlineContentDispositionTypes.includes(detectedMimeType)
+			? "inline"
+			: "attachment";
 
 		if (detectedMimeType === "audio/vnd.wave") {
 			// Send a more common mime type for wave audio files