diff --git a/packages/server/src/cli.ts b/packages/server/src/cli.ts
index e57a6af0d469..7486ebad9c78 100644
--- a/packages/server/src/cli.ts
+++ b/packages/server/src/cli.ts
@@ -8,6 +8,7 @@ import * as os from "os";
 import * as path from "path";
 import * as WebSocket from "ws";
 import { buildDir, cacheHome, dataHome, isCli, serveStatic } from "./constants";
+import { getRecentRelease } from "./updater";
 import { createApp } from "./server";
 import { forkModule, requireModule } from "./vscode/bootstrapFork";
 import { SharedProcess, SharedProcessState } from "./vscode/sharedProcess";
@@ -165,8 +166,6 @@ const bold = (text: string | number): string | number => {
 		}
 	}
 
-	logger.info(`\u001B[1mcode-server ${process.env.VERSION ? `v${process.env.VERSION}` : "development"}`);
-
 	if (options.dataDir) {
 		logger.warn('"--data-dir" is deprecated. Use "--user-data-dir" instead.');
 	}
@@ -191,7 +190,19 @@ const bold = (text: string | number): string | number => {
 		return;
 	}
 
-	// TODO: fill in appropriate doc url
+	if (isCli) {
+		const currentVersion = process.env.VERSION;
+		try {
+			const recentRelease = await getRecentRelease();
+			if (recentRelease !== currentVersion) {
+				logger.warn(`New version available! (\u001B[1m${recentRelease}\u001B[0m) https://github.com/codercom/code-server/releases/latest`);
+			}
+		} catch (err) {
+			logger.error(`Failed to check latest release: ${err}`);
+		}
+	}
+
+	logger.info(`\u001B[1mcode-server ${process.env.VERSION ? `v${process.env.VERSION}` : "development"}`);
 	logger.info("Additional documentation: http://github.com/codercom/code-server");
 	logger.info("Initializing", field("data-dir", dataDir), field("extensions-dir", extensionsDir), field("working-dir", workingDir), field("log-dir", logDir));
 	const sharedProcess = new SharedProcess(dataDir, extensionsDir, builtInExtensionsDir);
@@ -286,7 +297,6 @@ const bold = (text: string | number): string | number => {
 	});
 	if (!options.certKey && !options.cert) {
 		logger.warn("No certificate specified. \u001B[1mThis could be insecure.");
-		// TODO: fill in appropriate doc url
 		logger.warn("Documentation on securing your setup: https://github.com/codercom/code-server/blob/master/doc/security/ssl.md");
 	}
 
diff --git a/packages/server/src/updater.ts b/packages/server/src/updater.ts
new file mode 100644
index 000000000000..c2490b349e20
--- /dev/null
+++ b/packages/server/src/updater.ts
@@ -0,0 +1,32 @@
+import * as https from "https";
+
+export const getRecentRelease = (): Promise<string> => {
+	return new Promise<string>((resolve, reject):void  => {
+		https.get({
+			host: "api.github.com",
+			path: "/repos/cdr/code-server/releases/latest",
+			method: "GET",
+			agent: false,
+			headers: {
+				"User-Agent": "code-server",
+			},
+		}, (res) => {
+			if (res.statusCode !== 200) {
+				reject(Error("Failed to acquire release information"));
+			}
+			let body = "";
+			res.on("data", (chunk) => {
+				body += chunk;
+			});
+
+			res.on("end", () => {
+				try {
+					const release = JSON.parse(body);
+					resolve(release.name);
+				} catch (err) {
+					reject(err);
+				}
+			});
+		});
+	});
+};