diff --git a/app/src/lib/release-notes.ts b/app/src/lib/release-notes.ts
index c9590800fee..6043c3a1250 100644
--- a/app/src/lib/release-notes.ts
+++ b/app/src/lib/release-notes.ts
@@ -10,6 +10,7 @@ import { getVersion } from '../ui/lib/app-proxy'
 import { formatDate } from './format-date'
 import { offsetFromNow } from './offset-from'
 import { encodePathAsUrl } from './path'
+import { getUserAgent } from './http'
 
 // expects a release note entry to contain a header and then some text
 // example:
@@ -102,7 +103,9 @@ export async function getChangeLog(
     changelogURL.searchParams.set('limit', limit.toString())
   }
 
-  const response = await fetch(changelogURL.toString())
+  const response = await fetch(changelogURL.toString(), {
+    headers: { 'user-agent': getUserAgent() },
+  })
   if (response.ok) {
     const releases: ReadonlyArray<ReleaseMetadata> = await response.json()
     return releases
diff --git a/app/src/lib/stats/stats-store.ts b/app/src/lib/stats/stats-store.ts
index 27c99f8bb43..6bb2cb08189 100644
--- a/app/src/lib/stats/stats-store.ts
+++ b/app/src/lib/stats/stats-store.ts
@@ -36,6 +36,7 @@ import { isInApplicationFolder } from '../../ui/main-process-proxy'
 import { getRendererGUID } from '../get-renderer-guid'
 import { ValidNotificationPullRequestReviewState } from '../valid-notification-pull-request-review'
 import { useExternalCredentialHelperKey } from '../trampoline/use-external-credential-helper'
+import { getUserAgent } from '../http'
 
 type PullRequestReviewStatFieldInfix =
   | 'Approved'
@@ -424,7 +425,10 @@ export interface IStatsStore {
 const defaultPostImplementation = (body: Record<string, any>) =>
   fetch(StatsEndpoint, {
     method: 'POST',
-    headers: new Headers({ 'Content-Type': 'application/json' }),
+    headers: {
+      'Content-Type': 'application/json',
+      'user-agent': getUserAgent(),
+    },
     body: JSON.stringify(body),
   })
 
diff --git a/app/src/main-process/menu/build-test-menu.ts b/app/src/main-process/menu/build-test-menu.ts
index bad757febf4..0026f449e83 100644
--- a/app/src/main-process/menu/build-test-menu.ts
+++ b/app/src/main-process/menu/build-test-menu.ts
@@ -146,6 +146,10 @@ export function buildTestMenu() {
           label: 'Update banner',
           click: emit('test-update-banner'),
         },
+        {
+          label: 'Update banner (priority)',
+          click: emit('test-prioritized-update-banner'),
+        },
         {
           label: `Showcase Update banner`,
           click: emit('test-showcase-update-banner'),
diff --git a/app/src/main-process/menu/menu-event.ts b/app/src/main-process/menu/menu-event.ts
index 78dc361f0a2..93ca7880b07 100644
--- a/app/src/main-process/menu/menu-event.ts
+++ b/app/src/main-process/menu/menu-event.ts
@@ -82,6 +82,7 @@ const TestMenuEvents = [
   'test-undone-banner',
   'test-untrusted-server',
   'test-update-banner',
+  'test-prioritized-update-banner',
   'test-update-existing-git-lfs-filters',
   'test-upstream-already-exists',
 ] as const
diff --git a/app/src/ui/app.tsx b/app/src/ui/app.tsx
index a636924ed98..db2cc8fe977 100644
--- a/app/src/ui/app.tsx
+++ b/app/src/ui/app.tsx
@@ -3130,6 +3130,8 @@ export class App extends React.Component<IAppProps, IAppState> {
         isX64ToARM64ImmediateAutoUpdate={
           updateStore.state.isX64ToARM64ImmediateAutoUpdate
         }
+        prioritizeUpdate={updateStore.state.prioritizeUpdate}
+        prioritizeUpdateInfoUrl={updateStore.state.prioritizeUpdateInfoUrl}
         onDismissed={this.onUpdateAvailableDismissed}
         isUpdateShowcaseVisible={this.state.isUpdateShowcaseVisible}
         emoji={this.state.emoji}
diff --git a/app/src/ui/banners/banner.tsx b/app/src/ui/banners/banner.tsx
index 8b768b0a552..9c3762ae986 100644
--- a/app/src/ui/banners/banner.tsx
+++ b/app/src/ui/banners/banner.tsx
@@ -1,11 +1,13 @@
 import * as React from 'react'
 import { Octicon } from '../octicons'
 import * as octicons from '../octicons/octicons.generated'
+import classNames from 'classnames'
 
 interface IBannerProps {
   readonly id?: string
   readonly timeout?: number
   readonly dismissable?: boolean
+  readonly className?: string
   readonly onDismissed: () => void
 }
 
@@ -19,8 +21,9 @@ export class Banner extends React.Component<IBannerProps, {}> {
   private dismissalTimeoutId: number | null = null
 
   public render() {
+    const cn = classNames('banner', this.props.className)
     return (
-      <div id={this.props.id} className="banner" ref={this.banner}>
+      <div id={this.props.id} className={cn} ref={this.banner}>
         <div className="contents">{this.props.children}</div>
         {this.renderCloseButton()}
       </div>
diff --git a/app/src/ui/banners/update-available.tsx b/app/src/ui/banners/update-available.tsx
index fc1bbea495f..ea0bd6c14dd 100644
--- a/app/src/ui/banners/update-available.tsx
+++ b/app/src/ui/banners/update-available.tsx
@@ -24,31 +24,43 @@ interface IUpdateAvailableProps {
   readonly isUpdateShowcaseVisible: boolean
   readonly emoji: Map<string, Emoji>
   readonly onDismissed: () => void
+  readonly prioritizeUpdate: boolean
+  readonly prioritizeUpdateInfoUrl: string | undefined
 }
 
 /**
  * A component which tells the user an update is available and gives them the
  * option of moving into the future or being a luddite.
  */
-export class UpdateAvailable extends React.Component<
-  IUpdateAvailableProps,
-  {}
-> {
+export class UpdateAvailable extends React.Component<IUpdateAvailableProps> {
   public render() {
     return (
-      <Banner id="update-available" onDismissed={this.props.onDismissed}>
-        {!this.props.isUpdateShowcaseVisible && (
-          <Octicon
-            className="download-icon"
-            symbol={octicons.desktopDownload}
-          />
-        )}
-
+      <Banner
+        id="update-available"
+        className={this.props.prioritizeUpdate ? 'priority' : undefined}
+        dismissable={!this.props.prioritizeUpdate}
+        onDismissed={this.props.onDismissed}
+      >
+        {this.renderIcon()}
         {this.renderMessage()}
       </Banner>
     )
   }
 
+  private renderIcon() {
+    if (this.props.isUpdateShowcaseVisible) {
+      return null
+    }
+
+    if (this.props.prioritizeUpdate) {
+      return <Octicon className="warning-icon" symbol={octicons.alert} />
+    }
+
+    return (
+      <Octicon className="download-icon" symbol={octicons.desktopDownload} />
+    )
+  }
+
   private renderMessage = () => {
     if (this.props.isX64ToARM64ImmediateAutoUpdate) {
       return (
@@ -87,6 +99,26 @@ export class UpdateAvailable extends React.Component<
       )
     }
 
+    if (this.props.prioritizeUpdate) {
+      return (
+        <span onSubmit={this.updateNow}>
+          This version of GitHub Desktop is missing{' '}
+          {this.props.prioritizeUpdateInfoUrl ? (
+            <LinkButton uri={this.props.prioritizeUpdateInfoUrl}>
+              important updates
+            </LinkButton>
+          ) : (
+            'important updates'
+          )}
+          . Please{' '}
+          <LinkButton onClick={this.updateNow}>
+            restart GitHub Desktop
+          </LinkButton>{' '}
+          now to install pending updates.
+        </span>
+      )
+    }
+
     return (
       <span onSubmit={this.updateNow}>
         An updated version of GitHub Desktop is available and will be installed
diff --git a/app/src/ui/lib/test-ui-components/test-ui-components.ts b/app/src/ui/lib/test-ui-components/test-ui-components.ts
index 0db4c6dab15..8bba75729dc 100644
--- a/app/src/ui/lib/test-ui-components/test-ui-components.ts
+++ b/app/src/ui/lib/test-ui-components/test-ui-components.ts
@@ -156,6 +156,11 @@ export function showTestUI(
       })
     case 'test-update-banner':
       return showFakeUpdateBanner({})
+    case 'test-prioritized-update-banner':
+      return showFakeUpdateBanner({
+        isPriority: true,
+        priorityInfoUrl: 'https://desktop.github.com',
+      })
     case 'test-update-existing-git-lfs-filters':
       return dispatcher.showPopup({ type: PopupType.LFSAttributeMismatch })
     case 'test-upstream-already-exists':
@@ -179,6 +184,8 @@ export function showTestUI(
   function showFakeUpdateBanner(options: {
     isArm64?: boolean
     isShowcase?: boolean
+    isPriority?: boolean
+    priorityInfoUrl?: string
   }) {
     updateStore.setIsx64ToARM64ImmediateAutoUpdate(options.isArm64 === true)
 
@@ -187,6 +194,12 @@ export function showTestUI(
       return
     }
 
+    if (options.isPriority !== undefined) {
+      updateStore.setPrioritizeUpdate(options.isPriority)
+    }
+
+    updateStore.setPrioritizeUpdateInfoUrl(options.priorityInfoUrl)
+
     dispatcher.setUpdateBannerVisibility(true)
   }
 
diff --git a/app/src/ui/lib/update-store.ts b/app/src/ui/lib/update-store.ts
index 00b2b9728d6..ce26a5ab4fd 100644
--- a/app/src/ui/lib/update-store.ts
+++ b/app/src/ui/lib/update-store.ts
@@ -23,6 +23,7 @@ import { enableUpdateFromEmulatedX64ToARM64 } from '../../lib/feature-flag'
 import { offsetFromNow } from '../../lib/offset-from'
 import { gte, SemVer } from 'semver'
 import { getVersion } from './app-proxy'
+import { getUserAgent } from '../../lib/http'
 
 /** The last version a showcase was seen. */
 export const lastShowCaseVersionSeen = 'version-of-last-showcase'
@@ -50,6 +51,8 @@ export interface IUpdateState {
   lastSuccessfulCheck: Date | null
   isX64ToARM64ImmediateAutoUpdate: boolean
   newReleases: ReadonlyArray<ReleaseSummary> | null
+  prioritizeUpdate: boolean
+  prioritizeUpdateInfoUrl: string | undefined
 }
 
 /** A store which contains the current state of the auto updater. */
@@ -62,6 +65,16 @@ class UpdateStore {
 
   /** Is the most recent update check user initiated? */
   private userInitiatedUpdate = true
+  private _prioritizeUpdate = false
+  private _prioritizeUpdateInfoUrl: string | undefined = undefined
+
+  public get prioritizeUpdate() {
+    return this._prioritizeUpdate
+  }
+
+  public get prioritizeUpdateInfoUrl() {
+    return this._prioritizeUpdateInfoUrl
+  }
 
   public constructor() {
     const lastSuccessfulCheckTime = getNumber(lastSuccessfulCheckKey, 0)
@@ -127,6 +140,8 @@ class UpdateStore {
       (await isRunningUnderARM64Translation())
     this.status = UpdateStatus.UpdateReady
     this.emitDidChange()
+
+    this.updatePriorityUpdateStatus()
   }
 
   /**
@@ -168,6 +183,8 @@ class UpdateStore {
       lastSuccessfulCheck: this.lastSuccessfulCheck,
       newReleases: this.newReleases,
       isX64ToARM64ImmediateAutoUpdate: this.isX64ToARM64ImmediateAutoUpdate,
+      prioritizeUpdate: this.prioritizeUpdate,
+      prioritizeUpdateInfoUrl: this.prioritizeUpdateInfoUrl,
     }
   }
 
@@ -187,6 +204,7 @@ class UpdateStore {
     // button to crash the app if in the subsequent check, there is no update
     // available anymore due to a disabled update.
     if (this.status === UpdateStatus.UpdateReady) {
+      this.updatePriorityUpdateStatus()
       return
     }
 
@@ -252,6 +270,32 @@ class UpdateStore {
     quitAndInstallUpdate()
   }
 
+  private async updatePriorityUpdateStatus() {
+    try {
+      const response = await fetch(await this.getUpdatesUrl(false), {
+        method: 'HEAD',
+        headers: { 'user-agent': getUserAgent() },
+      })
+
+      const prioritizeUpdate =
+        response.headers.get('x-prioritize-update') === 'true'
+
+      const prioritizeUpdateInfoUrl =
+        response.headers.get('x-prioritize-update-info-url') ?? undefined
+
+      if (
+        this._prioritizeUpdate !== prioritizeUpdate ||
+        this._prioritizeUpdateInfoUrl !== prioritizeUpdateInfoUrl
+      ) {
+        this._prioritizeUpdate = prioritizeUpdate
+        this._prioritizeUpdateInfoUrl = prioritizeUpdateInfoUrl
+        this.emitDidChange()
+      }
+    } catch (e) {
+      log.error('Error updating priority update status', e)
+    }
+  }
+
   /**
    * Method to determine if we should show an update showcase call to action.
    *
@@ -302,6 +346,32 @@ class UpdateStore {
 
     this.isX64ToARM64ImmediateAutoUpdate = value
   }
+
+  /** This method has only been added for ease of testing the update banner in
+   * this state and as such is limite to dev and test environments */
+  public setPrioritizeUpdate(value: boolean) {
+    if (
+      __RELEASE_CHANNEL__ !== 'development' &&
+      __RELEASE_CHANNEL__ !== 'test'
+    ) {
+      return
+    }
+
+    this._prioritizeUpdate = value
+  }
+
+  /** This method has only been added for ease of testing the update banner in
+   * this state and as such is limite to dev and test environments */
+  public setPrioritizeUpdateInfoUrl(value: string | undefined) {
+    if (
+      __RELEASE_CHANNEL__ !== 'development' &&
+      __RELEASE_CHANNEL__ !== 'test'
+    ) {
+      return
+    }
+
+    this._prioritizeUpdateInfoUrl = value
+  }
 }
 
 /** The store which contains the current state of the auto updater. */
diff --git a/app/styles/_variables.scss b/app/styles/_variables.scss
index 495b88deb1e..98fe19c9a71 100644
--- a/app/styles/_variables.scss
+++ b/app/styles/_variables.scss
@@ -477,6 +477,12 @@ $overlay-background-color: rgba(0, 0, 0, 0.4);
   --dialog-information-color: #{$blue-400};
   --dialog-error-color: #{$red};
 
+  /** Banner */
+  --banner-warning-background: #{$yellow-100};
+  --banner-warning-text-color: var(--text-color);
+  --banner-warning-link-color: #046ee7;
+  --banner-warning-icon-color: #{darken($yellow-700, 10%)};
+
   /** File warning */
   --file-warning-background-color: #{$yellow-100};
   --file-warning-color: #{darken($yellow-700, 10%)};
diff --git a/app/styles/themes/_dark.scss b/app/styles/themes/_dark.scss
index 55bedc8ac5b..290c97ad9ce 100644
--- a/app/styles/themes/_dark.scss
+++ b/app/styles/themes/_dark.scss
@@ -376,6 +376,12 @@ body.theme-dark {
   --dialog-information-color: #{$blue-400};
   --dialog-error-color: #{$red-600};
 
+  /** Banner */
+  --banner-warning-background: #272216;
+  --banner-warning-text-color: var(--text-color);
+  --banner-warning-link-color: #6682ff;
+  --banner-warning-icon-color: #{$yellow-700};
+
   /** File warning */
   --file-warning-background-color: #{rgba($yellow-900, 0.4)};
   --file-warning-color: #{$yellow-700};
diff --git a/app/styles/ui/banners/_update-available.scss b/app/styles/ui/banners/_update-available.scss
index 2e1abd9aedf..c0d1e36073a 100644
--- a/app/styles/ui/banners/_update-available.scss
+++ b/app/styles/ui/banners/_update-available.scss
@@ -1,10 +1,21 @@
 #update-available {
-  .download-icon {
+  .download-icon,
+  .warning-icon {
     margin-right: var(--spacing);
+    color: var(--banner-warning-icon-color);
   }
 
   .banner-emoji {
     display: inline-block;
     margin-right: var(--spacing-half);
   }
+
+  &.priority {
+    background-color: var(--banner-warning-background);
+    color: var(--banner-warning-text-color);
+
+    a {
+      color: var(--banner-warning-link-color);
+    }
+  }
 }