diff --git a/packages/flutter/lib/src/cupertino/activity_indicator.dart b/packages/flutter/lib/src/cupertino/activity_indicator.dart
index b1c2e5ce62..fe93eb2456 100644
--- a/packages/flutter/lib/src/cupertino/activity_indicator.dart
+++ b/packages/flutter/lib/src/cupertino/activity_indicator.dart
@@ -28,7 +28,7 @@ const Color _kActiveTickColor = CupertinoDynamicColor.withBrightness(
 ///
 /// See also:
 ///
-///  * <https://developer.apple.com/ios/human-interface-guidelines/controls/progress-indicators/#activity-indicators>
+///  * <https://developer.apple.com/design/human-interface-guidelines/progress-indicators/>
 class CupertinoActivityIndicator extends StatefulWidget {
   /// Creates an iOS-style activity indicator that spins clockwise.
   const CupertinoActivityIndicator({
diff --git a/packages/flutter/lib/src/cupertino/button.dart b/packages/flutter/lib/src/cupertino/button.dart
index 73c90d01f1..bac428a653 100644
--- a/packages/flutter/lib/src/cupertino/button.dart
+++ b/packages/flutter/lib/src/cupertino/button.dart
@@ -35,7 +35,7 @@ const EdgeInsets _kBackgroundButtonPadding = EdgeInsets.symmetric(
 ///
 /// See also:
 ///
-///  * <https://developer.apple.com/ios/human-interface-guidelines/controls/buttons/>
+///  * <https://developer.apple.com/design/human-interface-guidelines/buttons/>
 class CupertinoButton extends StatefulWidget {
   /// Creates an iOS-style button.
   const CupertinoButton({
diff --git a/packages/flutter/lib/src/cupertino/dialog.dart b/packages/flutter/lib/src/cupertino/dialog.dart
index 6e0c22997c..93c77afb07 100644
--- a/packages/flutter/lib/src/cupertino/dialog.dart
+++ b/packages/flutter/lib/src/cupertino/dialog.dart
@@ -188,7 +188,7 @@ bool _isInAccessibilityMode(BuildContext context) {
 ///    holds arbitrary content to create custom popups.
 ///  * [CupertinoDialogAction], which is an iOS-style dialog button.
 ///  * [AlertDialog], a Material Design alert dialog.
-///  * <https://developer.apple.com/ios/human-interface-guidelines/views/alerts/>
+///  * <https://developer.apple.com/design/human-interface-guidelines/alerts/>
 class CupertinoAlertDialog extends StatefulWidget {
   /// Creates an iOS-style alert dialog.
   const CupertinoAlertDialog({
@@ -400,7 +400,7 @@ class _CupertinoAlertDialogState extends State<CupertinoAlertDialog> {
 ///
 ///  * [CupertinoAlertDialog], which is a dialog with a title, content, and
 ///    actions.
-///  * <https://developer.apple.com/ios/human-interface-guidelines/views/alerts/>
+///  * <https://developer.apple.com/design/human-interface-guidelines/alerts/>
 class CupertinoPopupSurface extends StatelessWidget {
   /// Creates an iOS-style rounded rectangle popup surface.
   const CupertinoPopupSurface({
diff --git a/packages/flutter/lib/src/cupertino/route.dart b/packages/flutter/lib/src/cupertino/route.dart
index 1a3d8fb522..90ee60b5d5 100644
--- a/packages/flutter/lib/src/cupertino/route.dart
+++ b/packages/flutter/lib/src/cupertino/route.dart
@@ -1288,7 +1288,7 @@ Widget _buildCupertinoDialogTransitions(BuildContext context, Animation<double>
 ///  * [showGeneralDialog], which allows for customization of the dialog popup.
 ///  * [DisplayFeatureSubScreen], which documents the specifics of how
 ///    [DisplayFeature]s can split the screen into sub-screens.
-///  * <https://developer.apple.com/ios/human-interface-guidelines/views/alerts/>
+///  * <https://developer.apple.com/design/human-interface-guidelines/alerts/>
 Future<T?> showCupertinoDialog<T>({
   required BuildContext context,
   required WidgetBuilder builder,
diff --git a/packages/flutter/lib/src/cupertino/slider.dart b/packages/flutter/lib/src/cupertino/slider.dart
index 94c967173c..df5758cb34 100644
--- a/packages/flutter/lib/src/cupertino/slider.dart
+++ b/packages/flutter/lib/src/cupertino/slider.dart
@@ -45,7 +45,7 @@ import 'thumb_painter.dart';
 ///
 /// See also:
 ///
-///  * <https://developer.apple.com/ios/human-interface-guidelines/controls/sliders/>
+///  * <https://developer.apple.com/design/human-interface-guidelines/sliders/>
 class CupertinoSlider extends StatefulWidget {
   /// Creates an iOS-style slider.
   ///
diff --git a/packages/flutter/lib/src/cupertino/switch.dart b/packages/flutter/lib/src/cupertino/switch.dart
index 3b297ba6ee..b864fd5e98 100644
--- a/packages/flutter/lib/src/cupertino/switch.dart
+++ b/packages/flutter/lib/src/cupertino/switch.dart
@@ -60,7 +60,7 @@ import 'thumb_painter.dart';
 /// See also:
 ///
 ///  * [Switch], the Material Design equivalent.
-///  * <https://developer.apple.com/ios/human-interface-guidelines/controls/switches/>
+///  * <https://developer.apple.com/design/human-interface-guidelines/toggles/>
 class CupertinoSwitch extends StatefulWidget {
   /// Creates an iOS-style switch.
   ///
diff --git a/packages/flutter/lib/src/material/typography.dart b/packages/flutter/lib/src/material/typography.dart
index 6749f109c0..771c4f6e20 100644
--- a/packages/flutter/lib/src/material/typography.dart
+++ b/packages/flutter/lib/src/material/typography.dart
@@ -60,7 +60,7 @@ enum ScriptCategory {
 /// [blackCupertino], and [whiteCupertino]. The Mountain View theme [TextStyle]s
 /// are based on the Roboto fonts as used on Android. The Cupertino themes are
 /// based on the [San Francisco
-/// font](https://developer.apple.com/ios/human-interface-guidelines/visual-design/typography/)
+/// font](https://developer.apple.com/design/human-interface-guidelines/typography/)
 /// fonts as used by Apple on iOS.
 ///
 /// Two sets of geometry themes are provided: 2014 and 2018. The 2014 themes
diff --git a/packages/flutter/lib/src/widgets/bottom_navigation_bar_item.dart b/packages/flutter/lib/src/widgets/bottom_navigation_bar_item.dart
index 30bb768cf4..5d4eb25acb 100644
--- a/packages/flutter/lib/src/widgets/bottom_navigation_bar_item.dart
+++ b/packages/flutter/lib/src/widgets/bottom_navigation_bar_item.dart
@@ -17,7 +17,7 @@ import 'framework.dart';
 ///  * [BottomNavigationBar]
 ///  * <https://material.io/design/components/bottom-navigation.html>
 ///  * [CupertinoTabBar]
-///  * <https://developer.apple.com/ios/human-interface-guidelines/bars/tab-bars>
+///  * <https://developer.apple.com/design/human-interface-guidelines/tab-bars/>
 class BottomNavigationBarItem {
   /// Creates an item that is used with [BottomNavigationBar.items].
   ///
diff --git a/packages/flutter/test/material/typography_test.dart b/packages/flutter/test/material/typography_test.dart
index c641979f03..b6d9765bc0 100644
--- a/packages/flutter/test/material/typography_test.dart
+++ b/packages/flutter/test/material/typography_test.dart
@@ -34,7 +34,7 @@ void main() {
     expect(Typography.material2018(platform: TargetPlatform.windows).white.titleLarge!.fontFamily, 'Segoe UI');
   });
 
-  // Ref: https://developer.apple.com/ios/human-interface-guidelines/visual-design/typography/
+  // Ref: https://developer.apple.com/design/human-interface-guidelines/typography/
   final Matcher isSanFranciscoDisplayFont = predicate((TextStyle s) {
     return s.fontFamily == 'CupertinoSystemDisplay';
   }, 'Uses SF Display font');