diff --git a/packages/flutter/lib/src/widgets/selectable_region.dart b/packages/flutter/lib/src/widgets/selectable_region.dart
index 0a33ee8e2dc..9a8b670a7c3 100644
--- a/packages/flutter/lib/src/widgets/selectable_region.dart
+++ b/packages/flutter/lib/src/widgets/selectable_region.dart
@@ -303,18 +303,21 @@ class SelectableRegion extends StatefulWidget {
   }) {
     final bool canCopy = selectionGeometry.status == SelectionStatus.uncollapsed;
     final bool canSelectAll = selectionGeometry.hasContent;
-    final bool platformCanShare = switch (defaultTargetPlatform) {
-      TargetPlatform.android => selectionGeometry.status == SelectionStatus.uncollapsed,
-      TargetPlatform.macOS ||
-      TargetPlatform.fuchsia ||
-      TargetPlatform.linux ||
-      TargetPlatform.windows => false,
-      // TODO(bleroux): the share button should be shown on iOS but the share
-      // functionality requires some changes on the engine side because, on iPad,
-      // it needs an anchor for the popup.
-      // See: https://github.com/flutter/flutter/issues/141775.
-      TargetPlatform.iOS => false,
-    };
+    // The share button is not supported on the web.
+    final bool platformCanShare =
+        !kIsWeb &&
+        switch (defaultTargetPlatform) {
+          TargetPlatform.android => selectionGeometry.status == SelectionStatus.uncollapsed,
+          TargetPlatform.macOS ||
+          TargetPlatform.fuchsia ||
+          TargetPlatform.linux ||
+          TargetPlatform.windows => false,
+          // TODO(bleroux): the share button should be shown on iOS but the share
+          // functionality requires some changes on the engine side because, on iPad,
+          // it needs an anchor for the popup.
+          // See: https://github.com/flutter/flutter/issues/141775.
+          TargetPlatform.iOS => false,
+        };
     final bool canShare = onShare != null && platformCanShare;
 
     // On Android, the share button is before the select all button.
@@ -410,7 +413,14 @@ class SelectableRegionState extends State<SelectableRegion>
   SelectedContent? _lastSelectedContent;
 
   /// Whether the native browser context menu is enabled.
-  bool get _webContextMenuEnabled => kIsWeb && BrowserContextMenu.enabled;
+  // TODO(Renzo-Olivares): Re-enable web context menu for Android
+  // and iOS when https://github.com/flutter/flutter/issues/177123
+  // is resolved.
+  bool get _webContextMenuEnabled =>
+      kIsWeb &&
+      BrowserContextMenu.enabled &&
+      defaultTargetPlatform != TargetPlatform.android &&
+      defaultTargetPlatform != TargetPlatform.iOS;
 
   /// The [SelectionOverlay] that is currently visible on the screen.
   ///
diff --git a/packages/flutter/test/material/selection_area_test.dart b/packages/flutter/test/material/selection_area_test.dart
index 5e38d566af8..7e865bbe25b 100644
--- a/packages/flutter/test/material/selection_area_test.dart
+++ b/packages/flutter/test/material/selection_area_test.dart
@@ -130,6 +130,50 @@ void main() {
     variant: const TargetPlatformVariant(<TargetPlatform>{TargetPlatform.iOS}),
   );
 
+  testWidgets(
+    'builds the default context menu by default on Android and iOS web',
+    (WidgetTester tester) async {
+      final FocusNode focusNode = FocusNode();
+      addTearDown(focusNode.dispose);
+
+      await tester.pumpWidget(
+        MaterialApp(
+          home: SelectionArea(focusNode: focusNode, child: const Text('How are you?')),
+        ),
+      );
+      await tester.pumpAndSettle();
+
+      expect(find.byType(AdaptiveTextSelectionToolbar), findsNothing);
+
+      // Show the toolbar by longpressing.
+      final RenderParagraph paragraph1 = tester.renderObject<RenderParagraph>(
+        find.descendant(of: find.text('How are you?'), matching: find.byType(RichText)),
+      );
+      final TestGesture gesture = await tester.startGesture(
+        textOffsetToPosition(paragraph1, 6),
+      ); // at the 'r'
+      addTearDown(gesture.removePointer);
+      await tester.pump(const Duration(milliseconds: 500));
+      // `are` is selected.
+      expect(paragraph1.selections[0], const TextSelection(baseOffset: 4, extentOffset: 7));
+
+      await gesture.up();
+      await tester.pumpAndSettle();
+
+      expect(find.byType(AdaptiveTextSelectionToolbar), findsOneWidget);
+    },
+    // TODO(Renzo-Olivares): Remove this test when the web context menu
+    // for Android and iOS is re-enabled.
+    // See: https://github.com/flutter/flutter/issues/177123.
+    // [intended] Android and iOS use the flutter rendered menu on the web.
+    skip:
+        !kIsWeb ||
+        !<TargetPlatform>{
+          TargetPlatform.android,
+          TargetPlatform.iOS,
+        }.contains(defaultTargetPlatform),
+  );
+
   testWidgets(
     'builds the default context menu by default',
     (WidgetTester tester) async {
diff --git a/packages/flutter/test/widgets/selectable_region_context_menu_test.dart b/packages/flutter/test/widgets/selectable_region_context_menu_test.dart
index 6ab42eaa78e..c7c1a70b416 100644
--- a/packages/flutter/test/widgets/selectable_region_context_menu_test.dart
+++ b/packages/flutter/test/widgets/selectable_region_context_menu_test.dart
@@ -24,6 +24,14 @@ extension on web.CSSRuleList {
       Iterable<web.CSSRule?>.generate(length, (int index) => item(index));
 }
 
+bool _browserContextMenuEnabled() {
+  // TODO(Renzo-Olivares): Remove this when the web context menu
+  // for Android and iOS is re-enabled.
+  // See: https://github.com/flutter/flutter/issues/177123.
+  return kIsWeb &&
+      !<TargetPlatform>{TargetPlatform.android, TargetPlatform.iOS}.contains(defaultTargetPlatform);
+}
+
 void main() {
   late FakePlatformViewRegistry fakePlatformViewRegistry;
 
@@ -39,128 +47,144 @@ void main() {
     PlatformSelectableRegionContextMenu.debugResetRegistry();
   });
 
-  testWidgets('DOM element is set up correctly', (WidgetTester tester) async {
-    final int currentViewId = platformViewsRegistry.getNextPlatformViewId();
+  testWidgets(
+    'DOM element is set up correctly',
+    (WidgetTester tester) async {
+      final int currentViewId = platformViewsRegistry.getNextPlatformViewId();
 
-    await tester.pumpWidget(
-      MaterialApp(
-        home: SelectableRegion(
-          selectionControls: EmptyTextSelectionControls(),
-          child: const Placeholder(),
+      await tester.pumpWidget(
+        MaterialApp(
+          home: SelectableRegion(
+            selectionControls: EmptyTextSelectionControls(),
+            child: const Placeholder(),
+          ),
         ),
-      ),
-    );
+      );
 
-    final web.HTMLElement element =
-        fakePlatformViewRegistry.getViewById(currentViewId + 1) as web.HTMLElement;
+      final web.HTMLElement element =
+          fakePlatformViewRegistry.getViewById(currentViewId + 1) as web.HTMLElement;
 
-    expect(element, isNotNull);
-    expect(element.style.width, '100%');
-    expect(element.style.height, '100%');
-    expect(element.classList.length, 1);
+      expect(element, isNotNull);
+      expect(element.style.width, '100%');
+      expect(element.style.height, '100%');
+      expect(element.classList.length, 1);
 
-    final int numberOfStyleElements = getNumberOfStyleElements();
-    expect(numberOfStyleElements, 1);
-  });
+      final int numberOfStyleElements = getNumberOfStyleElements();
+      expect(numberOfStyleElements, 1);
+    },
+    skip: !_browserContextMenuEnabled(), // [intended]
+  );
 
-  testWidgets('only one <style> is inserted into the DOM', (WidgetTester tester) async {
-    await tester.pumpWidget(
-      MaterialApp(
-        home: ListView(
-          children: <Widget>[
-            SelectableRegion(
-              selectionControls: EmptyTextSelectionControls(),
-              child: const Placeholder(),
-            ),
-            SelectableRegion(
-              selectionControls: EmptyTextSelectionControls(),
-              child: const Placeholder(),
-            ),
-            SelectableRegion(
-              selectionControls: EmptyTextSelectionControls(),
-              child: const Placeholder(),
-            ),
-          ],
+  testWidgets(
+    'only one <style> is inserted into the DOM',
+    (WidgetTester tester) async {
+      await tester.pumpWidget(
+        MaterialApp(
+          home: ListView(
+            children: <Widget>[
+              SelectableRegion(
+                selectionControls: EmptyTextSelectionControls(),
+                child: const Placeholder(),
+              ),
+              SelectableRegion(
+                selectionControls: EmptyTextSelectionControls(),
+                child: const Placeholder(),
+              ),
+              SelectableRegion(
+                selectionControls: EmptyTextSelectionControls(),
+                child: const Placeholder(),
+              ),
+            ],
+          ),
         ),
-      ),
-    );
-    await tester.pumpAndSettle();
-    await tester.pumpAndSettle();
+      );
+      await tester.pumpAndSettle();
+      await tester.pumpAndSettle();
 
-    final int numberOfStyleElements = getNumberOfStyleElements();
-    expect(numberOfStyleElements, 1);
-  });
+      final int numberOfStyleElements = getNumberOfStyleElements();
+      expect(numberOfStyleElements, 1);
+    },
+    skip: !_browserContextMenuEnabled(), // [intended]
+  );
 
-  testWidgets('right click can trigger select word', (WidgetTester tester) async {
-    final int currentViewId = platformViewsRegistry.getNextPlatformViewId();
+  testWidgets(
+    'right click can trigger select word',
+    (WidgetTester tester) async {
+      final int currentViewId = platformViewsRegistry.getNextPlatformViewId();
 
-    final FocusNode focusNode = FocusNode();
-    addTearDown(focusNode.dispose);
-    final UniqueKey spy = UniqueKey();
-    await tester.pumpWidget(
-      MaterialApp(
-        home: SelectableRegion(
-          focusNode: focusNode,
-          selectionControls: materialTextSelectionControls,
-          child: SelectionSpy(key: spy),
+      final FocusNode focusNode = FocusNode();
+      addTearDown(focusNode.dispose);
+      final UniqueKey spy = UniqueKey();
+      await tester.pumpWidget(
+        MaterialApp(
+          home: SelectableRegion(
+            focusNode: focusNode,
+            selectionControls: materialTextSelectionControls,
+            child: SelectionSpy(key: spy),
+          ),
         ),
-      ),
-    );
+      );
 
-    final web.HTMLElement element =
-        fakePlatformViewRegistry.getViewById(currentViewId + 1) as web.HTMLElement;
-    expect(element, isNotNull);
+      final web.HTMLElement element =
+          fakePlatformViewRegistry.getViewById(currentViewId + 1) as web.HTMLElement;
+      expect(element, isNotNull);
 
-    focusNode.requestFocus();
-    await tester.pump();
+      focusNode.requestFocus();
+      await tester.pump();
 
-    // Dispatch right click.
-    element.dispatchEvent(
-      web.MouseEvent('mousedown', web.MouseEventInit(button: 2, clientX: 200, clientY: 300)),
-    );
-    final RenderSelectionSpy renderSelectionSpy = tester.renderObject<RenderSelectionSpy>(
-      find.byKey(spy),
-    );
-    expect(renderSelectionSpy.events, isNotEmpty);
+      // Dispatch right click.
+      element.dispatchEvent(
+        web.MouseEvent('mousedown', web.MouseEventInit(button: 2, clientX: 200, clientY: 300)),
+      );
+      final RenderSelectionSpy renderSelectionSpy = tester.renderObject<RenderSelectionSpy>(
+        find.byKey(spy),
+      );
+      expect(renderSelectionSpy.events, isNotEmpty);
 
-    SelectWordSelectionEvent? selectWordEvent;
-    for (final SelectionEvent event in renderSelectionSpy.events) {
-      if (event is SelectWordSelectionEvent) {
-        selectWordEvent = event;
-        break;
+      SelectWordSelectionEvent? selectWordEvent;
+      for (final SelectionEvent event in renderSelectionSpy.events) {
+        if (event is SelectWordSelectionEvent) {
+          selectWordEvent = event;
+          break;
+        }
       }
-    }
-    expect(selectWordEvent, isNotNull);
-    expect((selectWordEvent!.globalPosition.dx - 200).abs() < precisionErrorTolerance, isTrue);
-    expect((selectWordEvent.globalPosition.dy - 300).abs() < precisionErrorTolerance, isTrue);
-  });
+      expect(selectWordEvent, isNotNull);
+      expect((selectWordEvent!.globalPosition.dx - 200).abs() < precisionErrorTolerance, isTrue);
+      expect((selectWordEvent.globalPosition.dy - 300).abs() < precisionErrorTolerance, isTrue);
+    },
+    skip: !_browserContextMenuEnabled(), // [intended]
+  );
 
   // Regression test for https://github.com/flutter/flutter/issues/157579
-  testWidgets('prevents default action of mousedown events', (WidgetTester tester) async {
-    final int currentViewId = platformViewsRegistry.getNextPlatformViewId();
+  testWidgets(
+    'prevents default action of mousedown events',
+    (WidgetTester tester) async {
+      final int currentViewId = platformViewsRegistry.getNextPlatformViewId();
 
-    await tester.pumpWidget(
-      MaterialApp(
-        home: SelectableRegion(
-          selectionControls: emptyTextSelectionControls,
-          child: const SizedBox.shrink(),
+      await tester.pumpWidget(
+        MaterialApp(
+          home: SelectableRegion(
+            selectionControls: emptyTextSelectionControls,
+            child: const SizedBox.shrink(),
+          ),
         ),
-      ),
-    );
-
-    final web.HTMLElement element =
-        fakePlatformViewRegistry.getViewById(currentViewId + 1) as web.HTMLElement;
-    expect(element, isNotNull);
-
-    for (int i = 0; i <= 4; i++) {
-      final web.MouseEvent event = web.MouseEvent(
-        'mousedown',
-        web.MouseEventInit(button: i, clientX: 200, clientY: 300, cancelable: true),
       );
-      element.dispatchEvent(event);
-      expect(event.defaultPrevented, isTrue);
-    }
-  });
+
+      final web.HTMLElement element =
+          fakePlatformViewRegistry.getViewById(currentViewId + 1) as web.HTMLElement;
+      expect(element, isNotNull);
+
+      for (int i = 0; i <= 4; i++) {
+        final web.MouseEvent event = web.MouseEvent(
+          'mousedown',
+          web.MouseEventInit(button: i, clientX: 200, clientY: 300, cancelable: true),
+        );
+        element.dispatchEvent(event);
+        expect(event.defaultPrevented, isTrue);
+      }
+    },
+    skip: !_browserContextMenuEnabled(), // [intended]
+  );
 }
 
 void removeAllStyleElements() {
diff --git a/packages/flutter/test/widgets/selectable_region_test.dart b/packages/flutter/test/widgets/selectable_region_test.dart
index bf5e4621a0c..c5a0cff7003 100644
--- a/packages/flutter/test/widgets/selectable_region_test.dart
+++ b/packages/flutter/test/widgets/selectable_region_test.dart
@@ -6446,6 +6446,56 @@ void main() {
       },
       skip: !kIsWeb, // [intended] This test verifies web behavior.
     );
+
+    testWidgets(
+      'uses contextMenuBuilder by default on Android and iOS web',
+      (WidgetTester tester) async {
+        final UniqueKey contextMenu = UniqueKey();
+
+        await tester.pumpWidget(
+          MaterialApp(
+            home: SelectableRegion(
+              selectionControls: materialTextSelectionHandleControls,
+              contextMenuBuilder:
+                  (BuildContext context, SelectableRegionState selectableRegionState) {
+                    return SizedBox.shrink(key: contextMenu);
+                  },
+              child: const Text('How are you?'),
+            ),
+          ),
+        );
+        await tester.pumpAndSettle();
+
+        expect(find.byKey(contextMenu), findsNothing);
+
+        // Show the toolbar by longpressing.
+        final RenderParagraph paragraph1 = tester.renderObject<RenderParagraph>(
+          find.descendant(of: find.text('How are you?'), matching: find.byType(RichText)),
+        );
+        final TestGesture gesture = await tester.startGesture(
+          textOffsetToPosition(paragraph1, 6),
+        ); // at the 'r'
+        addTearDown(gesture.removePointer);
+        await tester.pump(const Duration(milliseconds: 500));
+        // `are` is selected.
+        expect(paragraph1.selections[0], const TextSelection(baseOffset: 4, extentOffset: 7));
+
+        await gesture.up();
+        await tester.pumpAndSettle();
+
+        expect(find.byKey(contextMenu), findsOneWidget);
+      },
+      // TODO(Renzo-Olivares): Remove this test when the web context menu
+      // for Android and iOS is re-enabled.
+      // See: https://github.com/flutter/flutter/issues/177123.
+      // [intended] Android and iOS use the flutter rendered menu on the web.
+      skip:
+          !kIsWeb ||
+          !<TargetPlatform>{
+            TargetPlatform.android,
+            TargetPlatform.iOS,
+          }.contains(defaultTargetPlatform),
+    );
   });
 
   testWidgets('Multiple selectables on a single line should be in screen order', (