diff --git a/web/packages/design/src/ThemeProvider/index.tsx b/web/packages/design/src/ThemeProvider/index.tsx
index 4e064080dab66..7cd3db621e618 100644
--- a/web/packages/design/src/ThemeProvider/index.tsx
+++ b/web/packages/design/src/ThemeProvider/index.tsx
@@ -67,6 +67,19 @@ export function getPrefersDark(): boolean {
   );
 }
 
+export function updateFavicon() {
+  const darkModePreferred = getPrefersDark();
+  const favicon = document.querySelector('link[rel="icon"]');
+
+  if (favicon instanceof HTMLLinkElement) {
+    if (darkModePreferred) {
+      favicon.href = '/app/favicon-dark.png';
+    } else {
+      favicon.href = '/app/favicon-light.png';
+    }
+  }
+}
+
 const ThemeProvider = props => {
   const [themePreference, setThemePreference] = useState<Theme>(
     storageService.getThemePreference()
diff --git a/web/packages/teleport/index.html b/web/packages/teleport/index.html
index f6c081bbe15bc..34d6ce56782c2 100644
--- a/web/packages/teleport/index.html
+++ b/web/packages/teleport/index.html
@@ -12,13 +12,6 @@
       href="/app/favicon-light.png"
       rel="icon" 
       type="image/png" 
-      media="(prefers-color-scheme: light)"
-    />
-    <link
-      href="/app/favicon-dark.png"
-      rel="icon"
-      type="image/png" 
-      media="(prefers-color-scheme: dark)"
     />
     <title></title>
   </head>
diff --git a/web/packages/teleport/src/Teleport.tsx b/web/packages/teleport/src/Teleport.tsx
index b5c15090b3d00..83158e8e70062 100644
--- a/web/packages/teleport/src/Teleport.tsx
+++ b/web/packages/teleport/src/Teleport.tsx
@@ -16,8 +16,8 @@
  * along with this program.  If not, see <http://www.gnu.org/licenses/>.
  */
 
-import React, { Suspense } from 'react';
-import ThemeProvider from 'design/ThemeProvider';
+import React, { Suspense, useEffect } from 'react';
+import ThemeProvider, { updateFavicon } from 'design/ThemeProvider';
 
 import { Route, Router, Switch } from 'teleport/components/Router';
 import { CatchError } from 'teleport/components/CatchError';
@@ -55,6 +55,30 @@ const Teleport: React.FC<Props> = props => {
   const { ctx, history } = props;
   const createPublicRoutes = props.renderPublicRoutes || publicOSSRoutes;
   const createPrivateRoutes = props.renderPrivateRoutes || privateOSSRoutes;
+  // update the favicon based on the system pref, and listen if it changes
+  // overtime.
+  // TODO(avatus) this can be expanded upon eventually to handle the entire theme
+  // once we have a user settings page that allows users to properly set their theme
+  // to respect the system prefs. We only update the favicon here because the selected theme
+  // of the page doesn't necessarily match the theme of the browser, which is what we
+  // are trying to match.
+  useEffect(() => {
+    updateFavicon();
+
+    const colorSchemeQueryList = window.matchMedia(
+      '(prefers-color-scheme: dark)'
+    );
+
+    const colorSchemeListener = () => {
+      updateFavicon();
+    };
+
+    colorSchemeQueryList.addEventListener('change', colorSchemeListener);
+
+    return () => {
+      colorSchemeQueryList.removeEventListener('change', colorSchemeListener);
+    };
+  }, []);
 
   return (
     <CatchError>
diff --git a/web/packages/teleport/src/services/userPreferences/userPreferences.test.ts b/web/packages/teleport/src/services/userPreferences/userPreferences.test.ts
index 0595e3a19ecbd..e4b8ed3c30b8f 100644
--- a/web/packages/teleport/src/services/userPreferences/userPreferences.test.ts
+++ b/web/packages/teleport/src/services/userPreferences/userPreferences.test.ts
@@ -16,7 +16,11 @@
  * along with this program.  If not, see <http://www.gnu.org/licenses/>.
  */
 
-import { getCurrentTheme, getNextTheme } from 'design/ThemeProvider';
+import {
+  getCurrentTheme,
+  getNextTheme,
+  updateFavicon,
+} from 'design/ThemeProvider';
 import { Theme } from 'gen-proto-ts/teleport/userpreferences/v1/theme_pb';
 import { UserPreferences } from 'gen-proto-ts/teleport/userpreferences/v1/userpreferences_pb';
 
@@ -90,6 +94,66 @@ test('getCurrentTheme', () => {
   expect(currentTheme).toBe(Theme.DARK);
 });
 
+describe('updateFavicon', () => {
+  let originalMatchMedia: typeof window.matchMedia;
+
+  beforeAll(() => {
+    originalMatchMedia = window.matchMedia;
+  });
+
+  afterAll(() => {
+    window.matchMedia = originalMatchMedia;
+  });
+
+  beforeEach(() => {
+    document.body.innerHTML = '';
+    const link = document.createElement('link');
+    link.rel = 'icon';
+    link.href = '/initial-favicon.png';
+    document.head.appendChild(link);
+  });
+
+  test('set dark favicon when dark theme is preferred', () => {
+    window.matchMedia = jest.fn().mockImplementation(query => ({
+      matches: query === '(prefers-color-scheme: dark)',
+      media: query,
+      onchange: null,
+      addListener: jest.fn(),
+      removeListener: jest.fn(),
+      addEventListener: jest.fn(),
+      removeEventListener: jest.fn(),
+      dispatchEvent: jest.fn(),
+    }));
+
+    updateFavicon();
+
+    const favicon = document.querySelector(
+      'link[rel="icon"]'
+    ) as HTMLLinkElement;
+    expect(favicon.href).toContain('/app/favicon-dark.png');
+  });
+
+  test('set light favicon when light theme is preferred', () => {
+    window.matchMedia = jest.fn().mockImplementation(query => ({
+      matches: query !== '(prefers-color-scheme: dark)',
+      media: query,
+      onchange: null,
+      addListener: jest.fn(),
+      removeListener: jest.fn(),
+      addEventListener: jest.fn(),
+      removeEventListener: jest.fn(),
+      dispatchEvent: jest.fn(),
+    }));
+
+    updateFavicon();
+
+    const favicon = document.querySelector(
+      'link[rel="icon"]'
+    ) as HTMLLinkElement;
+    expect(favicon.href).toContain('/app/favicon-light.png');
+  });
+});
+
 test('getNextTheme', () => {
   mockMatchMediaWindow('dark');
   let nextTheme = getNextTheme(Theme.UNSPECIFIED);