diff --git a/src/browser/pages/home.css b/src/browser/pages/home.css
index c14a539a..018623ba 100644
--- a/src/browser/pages/home.css
+++ b/src/browser/pages/home.css
@@ -22,17 +22,24 @@
 }
 
 .block-row > .item {
-  color: #b6b6b6;
-  display: flex;
+  color: #c4c4c4;
   flex: 1;
+}
+
+.block-row > .item.-row {
+  display: flex;
+}
+
+.block-row > .item > .sub {
+  color: #888;
+}
+
+.block-row .-link {
+  cursor: pointer;
   text-decoration: none;
 }
 
-.block-row > .item.-link {
-  cursor: pointer;
-}
-
-.block-row > .item.-link:hover {
+.block-row .-link:hover {
   color: #fafafa;
 }
 
diff --git a/src/node/app/app.ts b/src/node/app/app.ts
index 62672e45..136c4cc6 100644
--- a/src/node/app/app.ts
+++ b/src/node/app/app.ts
@@ -115,7 +115,7 @@ export class MainHttpProvider extends HttpProvider {
 
   private getAppRow(app: Application): string {
     return `<div class="block-row">
-      <a class="item -link" href=".${app.path}">
+      <a class="item -row -link" href=".${app.path}">
         ${
           app.icon
             ? `<img class="icon" src="data:image/png;base64,${app.icon}"></img>`
@@ -139,17 +139,40 @@ export class MainHttpProvider extends HttpProvider {
       return "Updates are disabled"
     }
 
+    const humanize = (time: number): string => {
+      const d = new Date(time)
+      const pad = (t: number): string => (t < 10 ? "0" : "") + t
+      return (
+        `${d.getFullYear()}-${pad(d.getMonth() + 1)}-${pad(d.getDate())}` +
+        ` ${pad(d.getHours())}:${pad(d.getMinutes())}`
+      )
+    }
+
     const update = await this.update.getUpdate()
-    if (!update) {
+    if (this.update.isLatestVersion(update)) {
       return `<div class="block-row">
-        <span class="item">No updates available</span>
-        <span class="current" >Current: ${this.update.currentVersion}</span>
+        <div class="item">
+          ${update.version}
+          <div class="sub">Up to date</div>
+        </div>
+        <div class="item">
+          ${humanize(update.checked)}
+          <a class="sub -link" href="./update/check">Check now</a>
+        </div>
+        <div class="item" >Current: ${this.update.currentVersion}</div>
       </div>`
     }
 
     return `<div class="block-row">
-      <a class="item -link" href="./update">Update available: ${update.version}</a>
-      <span class="current" >Current: ${this.update.currentVersion}</span>
+      <a class="item -link" href="./update">
+        ${update.version}
+        <div class="sub">Out of date</div>
+      </a>
+      <div class="item">
+        ${humanize(update.checked)}
+        <a class="sub -link" href="./update/check">Check now</a>
+      </div>
+      <div class="item" >Current: ${this.update.currentVersion}</div>
     </div>`
   }
 }
diff --git a/src/node/app/update.ts b/src/node/app/update.ts
index 34df2cfc..55bb9dec 100644
--- a/src/node/app/update.ts
+++ b/src/node/app/update.ts
@@ -1,4 +1,5 @@
 import { field, logger } from "@coder/logger"
+import zip from "adm-zip"
 import * as cp from "child_process"
 import * as fs from "fs-extra"
 import * as http from "http"
@@ -10,14 +11,15 @@ import { Readable, Writable } from "stream"
 import * as tar from "tar-fs"
 import * as url from "url"
 import * as util from "util"
-import zip from "adm-zip"
 import * as zlib from "zlib"
 import { HttpCode, HttpError } from "../../common/http"
 import { HttpProvider, HttpProviderOptions, HttpResponse, Route } from "../http"
+import { settings } from "../settings"
 import { tmpdir } from "../util"
 import { ipcMain } from "../wrapper"
 
 export interface Update {
+  checked: number
   version: string
 }
 
@@ -25,7 +27,8 @@ export interface Update {
  * Update HTTP provider.
  */
 export class UpdateHttpProvider extends HttpProvider {
-  private update?: Promise<Update | undefined>
+  private update?: Promise<Update>
+  private updateInterval = 1000 * 60 * 60 * 24 // Milliseconds between update checks.
 
   public constructor(options: HttpProviderOptions, public readonly enabled: boolean) {
     super(options)
@@ -33,6 +36,10 @@ export class UpdateHttpProvider extends HttpProvider {
 
   public async handleRequest(route: Route, request: http.IncomingMessage): Promise<HttpResponse | undefined> {
     switch (route.base) {
+      case "/check":
+        this.ensureMethod(request)
+        this.getUpdate(true)
+        return { redirect: "/login" }
       case "/": {
         this.ensureMethod(request, ["GET", "POST"])
         if (route.requestPath !== "/index.html") {
@@ -70,29 +77,38 @@ export class UpdateHttpProvider extends HttpProvider {
   /**
    * Query for and return the latest update.
    */
-  public async getUpdate(): Promise<Update | undefined> {
+  public async getUpdate(force?: boolean): Promise<Update> {
     if (!this.enabled) {
       throw new Error("updates are not enabled")
     }
 
     if (!this.update) {
-      this.update = this._getUpdate()
+      this.update = this._getUpdate(force)
+      this.update.then(() => (this.update = undefined))
     }
 
     return this.update
   }
 
-  private async _getUpdate(): Promise<Update | undefined> {
+  private async _getUpdate(force?: boolean): Promise<Update> {
     const url = "https://api.github.com/repos/cdr/code-server/releases/latest"
+    const now = Date.now()
     try {
-      const buffer = await this.request(url)
-      const data = JSON.parse(buffer.toString())
-      const latest = { version: data.name }
-      logger.debug("Got latest version", field("latest", latest.version))
-      return this.isLatestVersion(latest) ? undefined : latest
+      let { update } = !force ? await settings.read() : { update: undefined }
+      if (!update || update.checked + this.updateInterval < now) {
+        const buffer = await this.request(url)
+        const data = JSON.parse(buffer.toString())
+        update = { checked: now, version: data.name as string }
+        settings.write({ update })
+      }
+      logger.debug("Got latest version", field("latest", update.version))
+      return update
     } catch (error) {
       logger.error("Failed to get latest version", field("error", error.message))
-      return undefined
+      return {
+        checked: now,
+        version: "unknown",
+      }
     }
   }
 
@@ -103,10 +119,14 @@ export class UpdateHttpProvider extends HttpProvider {
   /**
    * Return true if the currently installed version is the latest.
    */
-  private isLatestVersion(latest: Update): boolean {
+  public isLatestVersion(latest: Update): boolean {
     const version = this.currentVersion
     logger.debug("Comparing versions", field("current", version), field("latest", latest.version))
-    return latest.version === version || semver.lt(latest.version, version)
+    try {
+      return latest.version === version || semver.lt(latest.version, version)
+    } catch (error) {
+      return true
+    }
   }
 
   private async getUpdateHtml(): Promise<string> {
@@ -115,8 +135,8 @@ export class UpdateHttpProvider extends HttpProvider {
     }
 
     const update = await this.getUpdate()
-    if (!update) {
-      return "No updates available"
+    if (this.isLatestVersion(update)) {
+      throw new Error("No update available")
     }
 
     return `<button type="submit" class="apply">
@@ -128,7 +148,7 @@ export class UpdateHttpProvider extends HttpProvider {
   public async tryUpdate(route: Route): Promise<HttpResponse> {
     try {
       const update = await this.getUpdate()
-      if (!update) {
+      if (this.isLatestVersion(update)) {
         throw new Error("no update available")
       }
       await this.downloadUpdate(update)
diff --git a/src/node/app/vscode.ts b/src/node/app/vscode.ts
index ac8c973a..b3fafff5 100644
--- a/src/node/app/vscode.ts
+++ b/src/node/app/vscode.ts
@@ -17,17 +17,11 @@ import { HttpCode, HttpError } from "../../common/http"
 import { generateUuid } from "../../common/util"
 import { Args } from "../cli"
 import { HttpProvider, HttpProviderOptions, HttpResponse, Route } from "../http"
-import { SettingsProvider } from "../settings"
-import { xdgLocalDir } from "../util"
-
-export interface Settings {
-  lastVisited: StartPath
-}
+import { settings } from "../settings"
 
 export class VscodeHttpProvider extends HttpProvider {
   private readonly serverRootPath: string
   private readonly vsRootPath: string
-  private readonly settings = new SettingsProvider<Settings>(path.join(xdgLocalDir, "coder.json"))
   private _vscode?: Promise<cp.ChildProcess>
   private workbenchOptions?: WorkbenchOptions
 
@@ -178,12 +172,12 @@ export class VscodeHttpProvider extends HttpProvider {
 
   private async getRoot(request: http.IncomingMessage, route: Route): Promise<HttpResponse> {
     const remoteAuthority = request.headers.host as string
-    const settings = await this.settings.read()
+    const { lastVisited } = await settings.read()
     const startPath = await this.getFirstValidPath(
       [
         { url: route.query.workspace, workspace: true },
         { url: route.query.folder, workspace: false },
-        settings.lastVisited,
+        lastVisited,
         this.args._ && this.args._.length > 0 ? { url: this.args._[0] } : undefined,
       ],
       remoteAuthority
@@ -200,7 +194,7 @@ export class VscodeHttpProvider extends HttpProvider {
     this.workbenchOptions = options
 
     if (startPath) {
-      this.settings.write({
+      settings.write({
         lastVisited: startPath,
       })
     }
diff --git a/src/node/settings.ts b/src/node/settings.ts
index 6432a119..2b4a277c 100644
--- a/src/node/settings.ts
+++ b/src/node/settings.ts
@@ -1,6 +1,7 @@
 import * as fs from "fs-extra"
+import * as path from "path"
+import { extend, xdgLocalDir } from "./util"
 import { logger } from "@coder/logger"
-import { extend } from "./util"
 
 export type Settings = { [key: string]: Settings | string | boolean | number }
 
@@ -32,9 +33,28 @@ export class SettingsProvider<T> {
    */
   public async write(settings: Partial<T>): Promise<void> {
     try {
-      await fs.writeFile(this.settingsPath, JSON.stringify(extend(this.read(), settings)))
+      await fs.writeFile(this.settingsPath, JSON.stringify(extend(await this.read(), settings), null, 2))
     } catch (error) {
       logger.warn(error.message)
     }
   }
 }
+
+/**
+ * Global code-server settings.
+ */
+export interface CoderSettings {
+  lastVisited: {
+    url: string
+    workspace: boolean
+  }
+  update: {
+    checked: number
+    version: string
+  }
+}
+
+/**
+ * Global code-server settings file.
+ */
+export const settings = new SettingsProvider<CoderSettings>(path.join(xdgLocalDir, "coder.json"))