diff --git a/flutter/lib/src/sentry_replay_options.dart b/flutter/lib/src/sentry_replay_options.dart
index a6e83fec4..442dd4967 100644
--- a/flutter/lib/src/sentry_replay_options.dart
+++ b/flutter/lib/src/sentry_replay_options.dart
@@ -1,3 +1,4 @@
+import 'package:flutter/foundation.dart';
 import 'package:flutter/services.dart';
 import 'package:flutter/widgets.dart';
 import 'package:meta/meta.dart';
@@ -85,6 +86,30 @@ class SentryReplayOptions {
       rules.add(const SentryMaskingConstantRule<EditableText>(
           SentryMaskingDecision.mask));
     }
+
+    // In Debug mode, check if users explicitly masks (or unmasks) widgets that
+    // look like they should be masked, e.g. Videos, WebViews, etc.
+    if (kDebugMode) {
+      rules.add(
+          SentryMaskingCustomRule<Widget>((Element element, Widget widget) {
+        final type = widget.runtimeType.toString();
+        final regexp = 'video|webview|password|pinput|camera|chart';
+        if (RegExp(regexp, caseSensitive: false).hasMatch(type)) {
+          final optionsName = 'options.experimental.replay';
+          throw Exception(
+              'Widget "$widget" name matches widgets that should usually be '
+              'masked because they may contain sensitive data. Because this '
+              'widget comes from a third-party plugin or your code, Sentry '
+              'cannot reliably mask it in release builds (due to obfuscation).'
+              'Please mask it explicitly using $optionsName.mask<$type>(). '
+              'If you want to silence this exception and keep the widget '
+              'visible in captures, you can use $optionsName.unmask<$type>(). '
+              'Note: the RegExp matched is: $regexp (case insensitive).');
+        }
+        return SentryMaskingDecision.continueProcessing;
+      }));
+    }
+
     return SentryMaskingConfig(rules);
   }
 
diff --git a/flutter/test/replay/masking_config_test.dart b/flutter/test/replay/masking_config_test.dart
index 46e6a9926..fe79a74a7 100644
--- a/flutter/test/replay/masking_config_test.dart
+++ b/flutter/test/replay/masking_config_test.dart
@@ -120,10 +120,8 @@ void main() async {
           .map((rule) => rule.toString())
           // These normalize the string on VM & js & wasm:
           .map((str) => str.replaceAll(
-              RegExp(
-                  r"SentryMaskingDecision from:? [fF]unction '?_maskImagesExceptAssets[@(].*",
-                  dotAll: true),
-              'SentryMaskingDecision)'))
+              RegExp(r"=> SentryMaskingDecision from:? .*", dotAll: true),
+              '=> SentryMaskingDecision)'))
           .map((str) => str.replaceAll(
               ' from: (element, widget) => masking_config.SentryMaskingDecision.mask',
               ''))
@@ -136,7 +134,8 @@ void main() async {
         ...alwaysEnabledRules,
         '$SentryMaskingCustomRule<$Image>(Closure: (Element, Widget) => SentryMaskingDecision)',
         '$SentryMaskingConstantRule<$Text>(mask)',
-        '$SentryMaskingConstantRule<$EditableText>(mask)'
+        '$SentryMaskingConstantRule<$EditableText>(mask)',
+        '$SentryMaskingCustomRule<$Widget>(Closure: ($Element, $Widget) => $SentryMaskingDecision)'
       ]);
     });
 
@@ -148,6 +147,7 @@ void main() async {
       expect(rulesAsStrings(sut), [
         ...alwaysEnabledRules,
         '$SentryMaskingConstantRule<$Image>(mask)',
+        '$SentryMaskingCustomRule<$Widget>(Closure: ($Element, $Widget) => $SentryMaskingDecision)'
       ]);
     });
 
@@ -159,6 +159,7 @@ void main() async {
       expect(rulesAsStrings(sut), [
         ...alwaysEnabledRules,
         '$SentryMaskingCustomRule<$Image>(Closure: (Element, Widget) => SentryMaskingDecision)',
+        '$SentryMaskingCustomRule<$Widget>(Closure: ($Element, $Widget) => $SentryMaskingDecision)'
       ]);
     });
 
@@ -171,6 +172,7 @@ void main() async {
         ...alwaysEnabledRules,
         '$SentryMaskingConstantRule<$Text>(mask)',
         '$SentryMaskingConstantRule<$EditableText>(mask)',
+        '$SentryMaskingCustomRule<$Widget>(Closure: ($Element, $Widget) => $SentryMaskingDecision)'
       ]);
     });
 
@@ -179,7 +181,10 @@ void main() async {
         ..maskAllText = false
         ..maskAllImages = false
         ..maskAssetImages = false;
-      expect(rulesAsStrings(sut), alwaysEnabledRules);
+      expect(rulesAsStrings(sut), [
+        ...alwaysEnabledRules,
+        '$SentryMaskingCustomRule<$Widget>(Closure: ($Element, $Widget) => $SentryMaskingDecision)'
+      ]);
     });
 
     group('user rules', () {
@@ -187,7 +192,8 @@ void main() async {
         ...alwaysEnabledRules,
         '$SentryMaskingCustomRule<$Image>(Closure: (Element, Widget) => SentryMaskingDecision)',
         '$SentryMaskingConstantRule<$Text>(mask)',
-        '$SentryMaskingConstantRule<$EditableText>(mask)'
+        '$SentryMaskingConstantRule<$EditableText>(mask)',
+        '$SentryMaskingCustomRule<$Widget>(Closure: ($Element, $Widget) => $SentryMaskingDecision)'
       ];
       test('mask() takes precedence', () {
         final sut = SentryReplayOptions();
diff --git a/flutter/test/replay/test_widget.dart b/flutter/test/replay/test_widget.dart
index 2e8d257a2..7011dc610 100644
--- a/flutter/test/replay/test_widget.dart
+++ b/flutter/test/replay/test_widget.dart
@@ -35,6 +35,7 @@ Future<Element> pumpTestElement(WidgetTester tester,
                       Offstage(offstage: true, child: newImage()),
                       Text(dummyText),
                       Material(child: TextFormField()),
+                      Material(child: TextField()),
                       SizedBox(
                           width: 100,
                           height: 20,
diff --git a/flutter/test/replay/widget_filter_test.dart b/flutter/test/replay/widget_filter_test.dart
index ad76e9bfa..12fc20c3a 100644
--- a/flutter/test/replay/widget_filter_test.dart
+++ b/flutter/test/replay/widget_filter_test.dart
@@ -31,7 +31,7 @@ void main() async {
       final sut = createSut(redactText: true);
       final element = await pumpTestElement(tester);
       sut.obscure(element, 1.0, defaultBounds);
-      expect(sut.items.length, 5);
+      expect(sut.items.length, 6);
     });
 
     testWidgets('does not redact text when disabled', (tester) async {
@@ -53,12 +53,13 @@ void main() async {
       final sut = createSut(redactText: true);
       final element = await pumpTestElement(tester);
       sut.obscure(element, 1.0, defaultBounds);
-      expect(sut.items.length, 5);
+      expect(sut.items.length, 6);
       expect(boundsRect(sut.items[0]), '624x48');
       expect(boundsRect(sut.items[1]), '169x20');
       expect(boundsRect(sut.items[2]), '800x192');
       expect(boundsRect(sut.items[3]), '800x24');
-      expect(boundsRect(sut.items[4]), '50x20');
+      expect(boundsRect(sut.items[4]), '800x24');
+      expect(boundsRect(sut.items[5]), '50x20');
     });
   });