diff --git a/client/components/Sidebar.vue b/client/components/Sidebar.vue
index 742c2d33..724dac00 100644
--- a/client/components/Sidebar.vue
+++ b/client/components/Sidebar.vue
@@ -52,12 +52,22 @@
 					aria-controls="settings"
 					:aria-selected="$route.name === 'Settings'"
 			/></span>
-			<span class="tooltipped tooltipped-n tooltipped-no-touch" aria-label="Help"
+			<span
+				class="tooltipped tooltipped-n tooltipped-no-touch"
+				:aria-label="
+					$store.state.serverConfiguration.isUpdateAvailable
+						? 'Help\n(update available)'
+						: 'Help'
+				"
 				><router-link
 					to="/help"
 					tag="button"
 					active-class="active"
-					:class="['icon', 'help']"
+					:class="[
+						'icon',
+						'help',
+						{notified: $store.state.serverConfiguration.isUpdateAvailable},
+					]"
 					aria-label="Help"
 					role="tab"
 					aria-controls="help"
diff --git a/client/components/VersionChecker.vue b/client/components/VersionChecker.vue
index d9c390f1..f2dbc684 100644
--- a/client/components/VersionChecker.vue
+++ b/client/components/VersionChecker.vue
@@ -1,7 +1,7 @@
 <template>
 	<div id="version-checker" :class="[$store.state.versionStatus]">
 		<p v-if="$store.state.versionStatus === 'loading'">
-			Checking for updates...
+			Checking for updates…
 		</p>
 		<p v-if="$store.state.versionStatus === 'new-version'">
 			The Lounge <b>{{ $store.state.versionData.latest.version }}</b>
@@ -35,7 +35,7 @@
 		</template>
 		<template v-if="$store.state.versionStatus === 'error'">
 			<p>
-				Information about latest releases could not be retrieved.
+				Information about latest release could not be retrieved.
 			</p>
 
 			<button id="check-now" class="btn btn-small" @click="checkNow">Try again</button>
@@ -48,11 +48,6 @@ import socket from "../js/socket";
 
 export default {
 	name: "VersionChecker",
-	data() {
-		return {
-			status: "loading",
-		};
-	},
 	mounted() {
 		if (!this.$store.state.versionData) {
 			this.checkNow();
diff --git a/client/components/Windows/Changelog.vue b/client/components/Windows/Changelog.vue
index a516934b..55961d11 100644
--- a/client/components/Windows/Changelog.vue
+++ b/client/components/Windows/Changelog.vue
@@ -26,7 +26,7 @@
 					></div>
 				</template>
 				<template v-else>
-					<p>Unable to retrieve releases from GitHub.</p>
+					<p>Unable to retrieve changelog for current release from GitHub.</p>
 					<p>
 						<a
 							:href="
diff --git a/client/css/style.css b/client/css/style.css
index b5f427d0..e88b85c0 100644
--- a/client/css/style.css
+++ b/client/css/style.css
@@ -906,6 +906,18 @@ background on hover (unless active) */
 	border-radius: 5px;
 }
 
+#footer .help.notified::after {
+	content: "\f021";
+	position: absolute;
+	bottom: 10px;
+	right: 7px;
+	padding: 2px;
+	font-size: 10px;
+	border-radius: 50%;
+	color: var(--link-color);
+	background: var(--body-bg-color);
+}
+
 .window li,
 .window p,
 .window label,
diff --git a/client/js/socket-events/changelog.js b/client/js/socket-events/changelog.js
index f840e575..a952d3ed 100644
--- a/client/js/socket-events/changelog.js
+++ b/client/js/socket-events/changelog.js
@@ -24,6 +24,16 @@ socket.on("changelog", function(data) {
 	// When there is a button to refresh the checker available, display it when
 	// data is expired. Before that, server would return same information anyway.
 	if (data.expiresAt) {
-		setTimeout(() => store.commit("versionDataExpired", true), data.expiresAt - Date.now());
+		const expires = data.expiresAt - Date.now();
+
+		if (expires > 0) {
+			setTimeout(() => store.commit("versionDataExpired", true), expires);
+		} else {
+			store.commit("versionDataExpired", true);
+		}
 	}
 });
+
+socket.on("changelog:newversion", () => {
+	store.state.serverConfiguration.isUpdateAvailable = true;
+});
diff --git a/src/plugins/changelog.js b/src/plugins/changelog.js
index 0ae90222..5a64c704 100644
--- a/src/plugins/changelog.js
+++ b/src/plugins/changelog.js
@@ -1,13 +1,16 @@
 "use strict";
 
 const got = require("got");
+const colors = require("chalk");
 const log = require("../log");
 const pkg = require("../../package.json");
 
 const TIME_TO_LIVE = 15 * 60 * 1000; // 15 minutes, in milliseconds
 
 module.exports = {
+	isUpdateAvailable: false,
 	fetch,
+	checkForUpdates,
 };
 
 const versions = {
@@ -17,8 +20,10 @@ const versions = {
 };
 
 async function fetch() {
+	const time = Date.now();
+
 	// Serving information from cache
-	if (versions.current.changelog) {
+	if (versions.expiresAt > time) {
 		return versions;
 	}
 
@@ -36,11 +41,8 @@ async function fetch() {
 
 		updateVersions(response);
 
-		// Emptying cached information after reaching said expiration date
-		setTimeout(() => {
-			delete versions.current.changelog;
-			delete versions.latest;
-		}, TIME_TO_LIVE);
+		// Add expiration date to the data to send to the client for later refresh
+		versions.expiresAt = time + TIME_TO_LIVE;
 	} catch (error) {
 		log.error(`Failed to fetch changelog: ${error}`);
 	}
@@ -74,6 +76,8 @@ function updateVersions(response) {
 
 			// Find latest release or pre-release if current version is also a pre-release
 			if (!release.prerelease || release.prerelease === prerelease) {
+				module.exports.isUpdateAvailable = true;
+
 				versions.latest = {
 					prerelease: release.prerelease,
 					version: release.tag_name,
@@ -84,7 +88,26 @@ function updateVersions(response) {
 			}
 		}
 	}
-
-	// Add expiration date to the data to send to the client for later refresh
-	versions.expiresAt = Date.now() + TIME_TO_LIVE;
+}
+
+function checkForUpdates(manager) {
+	fetch().then((versionData) => {
+		if (!module.exports.isUpdateAvailable) {
+			// Check for updates every 24 hours + random jitter of <3 hours
+			setTimeout(checkForUpdates, 24 * 3600 * 1000 + Math.floor(Math.random() * 10000000));
+		}
+
+		if (!versionData.latest) {
+			return;
+		}
+
+		log.info(
+			`The Lounge ${colors.green(
+				versionData.latest.version
+			)} is available. Read more on GitHub: ${versionData.latest.url}`
+		);
+
+		// Notify all connected clients about the new version
+		manager.clients.forEach((client) => client.emit("changelog:newversion"));
+	});
 }
diff --git a/src/server.js b/src/server.js
index 56be2578..6827daa7 100644
--- a/src/server.js
+++ b/src/server.js
@@ -239,6 +239,8 @@ module.exports = function(options = {}) {
 		if (Helper.config.prefetchStorage) {
 			require("./plugins/storage").emptyDir();
 		}
+
+		changelog.checkForUpdates(manager);
 	});
 
 	return server;
@@ -703,6 +705,7 @@ function getClientConfiguration() {
 		]);
 	}
 
+	config.isUpdateAvailable = changelog.isUpdateAvailable;
 	config.applicationServerKey = manager.webPush.vapidKeys.publicKey;
 	config.version = pkg.version;
 	config.gitCommit = Helper.getGitCommit();
diff --git a/test/plugins/auth/ldap.js b/test/plugins/auth/ldap.js
index 46703de6..d3adfe91 100644
--- a/test/plugins/auth/ldap.js
+++ b/test/plugins/auth/ldap.js
@@ -129,12 +129,9 @@ describe("LDAP authentication plugin", function() {
 	this.slow(200);
 
 	let server;
-	let originalLogInfo;
 
 	before(function(done) {
-		originalLogInfo = log.info;
-
-		log.info = () => {};
+		stub(log, "info");
 
 		server = startLdapServer(done);
 	});
@@ -142,7 +139,7 @@ describe("LDAP authentication plugin", function() {
 	after(function() {
 		server.close();
 
-		log.info = originalLogInfo;
+		log.info.restore();
 	});
 
 	beforeEach(function() {
diff --git a/test/server.js b/test/server.js
index cf6ebbe3..c33c9ae2 100644
--- a/test/server.js
+++ b/test/server.js
@@ -3,28 +3,28 @@
 const log = require("../src/log");
 const Helper = require("../src/helper");
 const expect = require("chai").expect;
+const stub = require("sinon").stub;
 const got = require("got");
 const io = require("socket.io-client");
+const changelog = require("../src/plugins/changelog");
 
 describe("Server", function() {
 	// Increase timeout due to unpredictable I/O on CI services
 	this.timeout(process.env.CI ? 25000 : 5000);
 
 	let server;
-	let originalLogInfo;
 
 	before(function() {
-		originalLogInfo = log.info;
-
-		log.info = () => {};
+		stub(log, "info");
+		stub(changelog, "checkForUpdates");
 
 		server = require("../src/server")();
 	});
 
 	after(function(done) {
 		server.close(done);
-
-		log.info = originalLogInfo;
+		log.info.restore();
+		changelog.checkForUpdates.restore();
 	});
 
 	const webURL = `http://${Helper.config.host}:${Helper.config.port}/`;
diff --git a/test/tests/mergeConfig.js b/test/tests/mergeConfig.js
index d14b1200..f2ddb449 100644
--- a/test/tests/mergeConfig.js
+++ b/test/tests/mergeConfig.js
@@ -248,9 +248,7 @@ describe("mergeConfig", function() {
 	});
 
 	it("should only merge same type", function() {
-		const originalLog = log.info;
-
-		log.warn = () => {};
+		stub(log, "warn");
 
 		expect(
 			mergeConfig(
@@ -282,6 +280,6 @@ describe("mergeConfig", function() {
 			shouldBeString: "string",
 		});
 
-		log.warn = originalLog;
+		log.warn.restore();
 	});
 });