diff --git a/pkg/analyzer/lib/src/error/type_arguments_verifier.dart b/pkg/analyzer/lib/src/error/type_arguments_verifier.dart
index 83fbc885965..3c3ce2d40e7 100644
--- a/pkg/analyzer/lib/src/error/type_arguments_verifier.dart
+++ b/pkg/analyzer/lib/src/error/type_arguments_verifier.dart
@@ -8,12 +8,14 @@ import 'package:analyzer/dart/analysis/features.dart';
 import 'package:analyzer/dart/ast/ast.dart';
 import 'package:analyzer/dart/element/element.dart';
 import 'package:analyzer/dart/element/type.dart';
+import 'package:analyzer/diagnostic/diagnostic.dart';
 import 'package:analyzer/error/error.dart';
 import 'package:analyzer/error/listener.dart';
 import 'package:analyzer/src/dart/ast/extensions.dart';
 import 'package:analyzer/src/dart/element/type_algebra.dart';
 import 'package:analyzer/src/dart/element/type_schema.dart';
 import 'package:analyzer/src/dart/element/type_system.dart';
+import 'package:analyzer/src/diagnostic/diagnostic.dart';
 import 'package:analyzer/src/error/codes.dart';
 import 'package:analyzer/src/generated/engine.dart' show AnalysisOptionsImpl;
 import 'package:analyzer/src/generated/resolver.dart';
@@ -265,18 +267,21 @@ class TypeArgumentsVerifier {
   /// Verify that the type arguments in the given [namedType] are all within
   /// their bounds.
   void _checkForTypeArgumentNotMatchingBounds(NamedType namedType) {
-    var type = namedType.type;
+    final type = namedType.type;
     if (type == null) {
       return;
     }
 
-    List<TypeParameterElement> typeParameters;
-    List<DartType> typeArguments;
-    var alias = type.alias;
+    final List<TypeParameterElement> typeParameters;
+    final String elementName;
+    final List<DartType> typeArguments;
+    final alias = type.alias;
     if (alias != null) {
+      elementName = alias.element.name;
       typeParameters = alias.element.typeParameters;
       typeArguments = alias.typeArguments;
     } else if (type is InterfaceType) {
+      elementName = type.element.name;
       typeParameters = type.element.typeParameters;
       typeArguments = type.typeArguments;
     } else {
@@ -289,7 +294,7 @@ class TypeArgumentsVerifier {
 
     // Check for regular-bounded.
     List<_TypeArgumentIssue>? issues;
-    var substitution = Substitution.fromPairs(typeParameters, typeArguments);
+    final substitution = Substitution.fromPairs(typeParameters, typeArguments);
     for (var i = 0; i < typeArguments.length; i++) {
       var typeParameter = typeParameters[i];
       var typeArgument = typeArguments[i];
@@ -325,6 +330,49 @@ class TypeArgumentsVerifier {
       return;
     }
 
+    List<DiagnosticMessage>? buildContextMessages({
+      List<DartType>? invertedTypeArguments,
+    }) {
+      final messages = <DiagnosticMessage>[];
+
+      void addMessage(String message) {
+        messages.add(
+          DiagnosticMessageImpl(
+            filePath: _errorReporter.source.fullName,
+            length: namedType.length,
+            message: message,
+            offset: namedType.offset,
+            url: null,
+          ),
+        );
+      }
+
+      String typeArgumentsToString(List<DartType> typeArguments) {
+        return typeArguments
+            .map((e) => e.getDisplayString(withNullability: true))
+            .join(', ');
+      }
+
+      if (namedType.typeArguments == null) {
+        var typeStr = '$elementName<${typeArgumentsToString(typeArguments)}>';
+        addMessage(
+          "The raw type was instantiated as '$typeStr', "
+          "and is not regular-bounded.",
+        );
+      }
+
+      if (invertedTypeArguments != null) {
+        var invertedTypeStr =
+            '$elementName<${typeArgumentsToString(invertedTypeArguments)}>';
+        addMessage(
+          "The inverted type '$invertedTypeStr' is also not regular-bounded, "
+          "so the type is not well-bounded.",
+        );
+      }
+
+      return messages.isNotEmpty ? messages : null;
+    }
+
     // If not allowed to be super-bounded, report issues.
     if (!_shouldAllowSuperBoundedTypes(namedType)) {
       for (var issue in issues) {
@@ -332,27 +380,32 @@ class TypeArgumentsVerifier {
           CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS,
           _typeArgumentErrorNode(namedType, issue.index),
           [issue.argument, issue.parameter.name, issue.parameterBound],
+          buildContextMessages(),
         );
       }
       return;
     }
 
     // Prepare type arguments for checking for super-bounded.
-    type = _typeSystem.replaceTopAndBottom(type);
-    alias = type.alias;
-    if (alias != null) {
-      typeArguments = alias.typeArguments;
-    } else if (type is InterfaceType) {
-      typeArguments = type.typeArguments;
+    final invertedType = _typeSystem.replaceTopAndBottom(type);
+    final List<DartType> invertedTypeArguments;
+    final invertedAlias = invertedType.alias;
+    if (invertedAlias != null) {
+      invertedTypeArguments = invertedAlias.typeArguments;
+    } else if (invertedType is InterfaceType) {
+      invertedTypeArguments = invertedType.typeArguments;
     } else {
       return;
     }
 
     // Check for super-bounded.
-    substitution = Substitution.fromPairs(typeParameters, typeArguments);
-    for (var i = 0; i < typeArguments.length; i++) {
+    final invertedSubstitution = Substitution.fromPairs(
+      typeParameters,
+      invertedTypeArguments,
+    );
+    for (var i = 0; i < invertedTypeArguments.length; i++) {
       var typeParameter = typeParameters[i];
-      var typeArgument = typeArguments[i];
+      var typeArgument = invertedTypeArguments[i];
 
       var bound = typeParameter.bound;
       if (bound == null) {
@@ -360,13 +413,16 @@ class TypeArgumentsVerifier {
       }
 
       bound = _libraryElement.toLegacyTypeIfOptOut(bound);
-      bound = substitution.substituteType(bound);
+      bound = invertedSubstitution.substituteType(bound);
 
       if (!_typeSystem.isSubtypeOf(typeArgument, bound)) {
         _errorReporter.reportErrorForNode(
           CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS,
           _typeArgumentErrorNode(namedType, i),
           [typeArgument, typeParameter.name, bound],
+          buildContextMessages(
+            invertedTypeArguments: invertedTypeArguments,
+          ),
         );
       }
     }
diff --git a/pkg/analyzer/test/generated/strong_mode_test.dart b/pkg/analyzer/test/generated/strong_mode_test.dart
index 11b6ce109f4..e23271d4401 100644
--- a/pkg/analyzer/test/generated/strong_mode_test.dart
+++ b/pkg/analyzer/test/generated/strong_mode_test.dart
@@ -3508,8 +3508,10 @@ void test() {
 class C<T0 extends List<T1>, T1 extends List<T0>> {}
 class D extends C {}
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 69, 1),
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 69, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 69, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 69, 1)]),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 69, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 69, 1)]),
     ]);
   }
 
@@ -3523,8 +3525,9 @@ void test() {
 }
 ''', [
       error(HintCode.UNUSED_LOCAL_VARIABLE, 73, 1),
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 81, 1),
       error(CompileTimeErrorCode.COULD_NOT_INFER, 81, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 81, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 81, 1)]),
     ]);
     _assertLocalVarType('c', 'C<List<dynamic>, List<List<dynamic>>>');
   }
@@ -3560,7 +3563,11 @@ typedef T F<T>(T x);
 class C<T extends F<T>> {}
 C c;
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 48, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 48, 1,
+          contextMessages: [
+            message('/home/test/lib/test.dart', 48, 1),
+            message('/home/test/lib/test.dart', 48, 1)
+          ]),
     ]);
     _assertTopVarType('c', 'C<dynamic Function(dynamic)>');
   }
diff --git a/pkg/analyzer/test/src/dart/resolution/constructor_reference_test.dart b/pkg/analyzer/test/src/dart/resolution/constructor_reference_test.dart
index 21f09c6a8db..46d6e0d5198 100644
--- a/pkg/analyzer/test/src/dart/resolution/constructor_reference_test.dart
+++ b/pkg/analyzer/test/src/dart/resolution/constructor_reference_test.dart
@@ -562,7 +562,8 @@ A<String> Function() bar() {
   return A.foo;
 }
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 41, 6),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 41, 6,
+          contextMessages: [message('/home/test/lib/test.dart', 39, 9)]),
     ]);
 
     var classElement = findElement.class_('A');
diff --git a/pkg/analyzer/test/src/dart/resolution/type_literal_test.dart b/pkg/analyzer/test/src/dart/resolution/type_literal_test.dart
index 817267045d1..866b8c30f36 100644
--- a/pkg/analyzer/test/src/dart/resolution/type_literal_test.dart
+++ b/pkg/analyzer/test/src/dart/resolution/type_literal_test.dart
@@ -75,7 +75,8 @@ var t = C<int, int>;
 class C<T extends num> {}
 var t = C<String>;
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 36, 6),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 36, 6,
+          contextMessages: [message('/home/test/lib/test.dart', 34, 9)]),
     ]);
 
     var typeLiteral = findNode.typeLiteral('C<String>;');
@@ -142,7 +143,8 @@ class C<T> {}
 typedef CA<T extends num> = C<T>;
 var t = CA<String>;
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 59, 6),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 59, 6,
+          contextMessages: [message('/home/test/lib/test.dart', 56, 10)]),
     ]);
 
     var typeLiteral = findNode.typeLiteral('CA<String>;');
@@ -374,7 +376,8 @@ var t = Fn<int, String>;
 typedef Fn<T extends num> = void Function(T);
 var t = Fn<String>;
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 57, 6),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 57, 6,
+          contextMessages: [message('/home/test/lib/test.dart', 54, 10)]),
     ]);
 
     var typeLiteral = findNode.typeLiteral('Fn<String>;');
diff --git a/pkg/analyzer/test/src/diagnostics/could_not_infer_test.dart b/pkg/analyzer/test/src/diagnostics/could_not_infer_test.dart
index 40b9bce2544..3e89e8fe8cb 100644
--- a/pkg/analyzer/test/src/diagnostics/could_not_infer_test.dart
+++ b/pkg/analyzer/test/src/diagnostics/could_not_infer_test.dart
@@ -33,10 +33,12 @@ main() {
   P._();
 }
 ''', [
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 154, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 154, 1)]),
       error(CompileTimeErrorCode.COULD_NOT_INFER, 154, 3),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 154, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 154, 1)]),
       error(CompileTimeErrorCode.COULD_NOT_INFER, 154, 3),
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 154, 1),
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 154, 1),
     ]);
   }
 
@@ -58,8 +60,9 @@ main() {
 }
 ''', [
       error(HintCode.UNUSED_LOCAL_VARIABLE, 120, 1),
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 124, 1),
       error(CompileTimeErrorCode.COULD_NOT_INFER, 124, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 124, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 124, 1)]),
     ]);
   }
 
diff --git a/pkg/analyzer/test/src/diagnostics/type_argument_not_matching_bounds_test.dart b/pkg/analyzer/test/src/diagnostics/type_argument_not_matching_bounds_test.dart
index 79ab24abf92..3149899b2c4 100644
--- a/pkg/analyzer/test/src/diagnostics/type_argument_not_matching_bounds_test.dart
+++ b/pkg/analyzer/test/src/diagnostics/type_argument_not_matching_bounds_test.dart
@@ -129,7 +129,8 @@ class C {
   C(G<B> this.f) {}
 }
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 71, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 71, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 69, 4)]),
     ]);
   }
 
@@ -140,7 +141,8 @@ class B {}
 class G<E extends A> {}
 G<B> f() => throw 0;
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 48, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 48, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 46, 4)]),
     ]);
   }
 
@@ -151,7 +153,8 @@ class B {}
 class G<E extends A> {}
 typedef G<B> f();
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 56, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 56, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 54, 4)]),
     ]);
   }
 
@@ -162,7 +165,8 @@ class B {}
 class G<E extends A> {}
 f(G<B> h()) {}
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 50, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 50, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 48, 4)]),
     ]);
   }
 
@@ -184,7 +188,8 @@ class B {}
 class G<E extends A> {}
 var b = 1 is G<B>;
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 61, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 61, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 59, 4)]),
     ]);
   }
 
@@ -252,7 +257,8 @@ class C {
   G<B> m() => throw 0;
 }
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 60, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 60, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 58, 4)]),
     ]);
   }
 
@@ -297,7 +303,8 @@ class Bar<T extends Foo<T>> {}
 class Baz extends Bar {}
 void main() {}
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 65, 3),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 65, 3,
+          contextMessages: [message('/home/test/lib/test.dart', 65, 3)]),
     ]);
     // Instantiate-to-bounds should have instantiated "Bar" to "Bar<Foo>".
     assertType(result.unit.declaredElement!.getType('Baz')!.supertype,
@@ -311,7 +318,8 @@ class B {}
 typedef F<T extends A>();
 F<B> fff = (throw 42);
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 50, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 50, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 48, 4)]),
     ]);
   }
 
@@ -350,7 +358,8 @@ class B {}
 class G<E extends A> {}
 f(G<B> g) {}
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 50, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 50, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 48, 4)]),
     ]);
   }
 
@@ -376,7 +385,8 @@ class C<E> {}
 class D<E extends A> {}
 C<D<B>> c = (throw 0);
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 64, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 64, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 62, 4)]),
     ]);
   }
 
@@ -388,7 +398,8 @@ class C {}
 class G<E extends A> {}
 class D<F extends G<B>> {}
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 77, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 77, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 75, 4)]),
     ]);
   }
 
@@ -399,7 +410,8 @@ class B {}
 class G<E extends A> {}
 G<B> g = (throw 0);
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 48, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 48, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 46, 4)]),
     ]);
   }
 
@@ -487,7 +499,8 @@ typedef FB<T extends F> = S Function<S extends T>(S);
 class CB<T extends F> {}
 void f(CB<FB<F>> a) {}
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 119, 5),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 119, 5,
+          contextMessages: [message('/home/test/lib/test.dart', 116, 9)]),
     ]);
   }
 
@@ -613,7 +626,8 @@ typedef X<T> = A;
 class A<T extends A<T>> {}
 typedef X<T> = A;
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 42, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 42, 1,
+          contextMessages: [message('/home/test/lib/test.dart', 42, 1)]),
     ]);
   }
 
@@ -623,7 +637,8 @@ class A {}
 typedef X<T extends A> = Map<int, T>;
 void f(X<String> a) {}
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 58, 6),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 58, 6,
+          contextMessages: [message('/home/test/lib/test.dart', 56, 9)]),
     ]);
   }
 
@@ -642,7 +657,11 @@ typedef A<X> = X Function(X);
 typedef G<X extends A<X>> = void Function<Y extends X>();
 foo(G g) {}
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 92, 1),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 92, 1,
+          contextMessages: [
+            message('/home/test/lib/test.dart', 92, 1),
+            message('/home/test/lib/test.dart', 92, 1)
+          ]),
     ]);
   }
 
@@ -698,7 +717,8 @@ A get foo => throw 0;
 class C<T extends int> {}
 var t = C<String>;
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 36, 6),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 36, 6,
+          contextMessages: [message('/home/test/lib/test.dart', 34, 9)]),
     ]);
   }
 
@@ -707,7 +727,8 @@ var t = C<String>;
 typedef Cb<T extends int> = void Function();
 var t = Cb<String>;
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 56, 6),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 56, 6,
+          contextMessages: [message('/home/test/lib/test.dart', 53, 10)]),
     ]);
   }
 
@@ -717,7 +738,8 @@ class C {}
 typedef D<T extends int> = C;
 var t = D<String>;
 ''', [
-      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 51, 6),
+      error(CompileTimeErrorCode.TYPE_ARGUMENT_NOT_MATCHING_BOUNDS, 51, 6,
+          contextMessages: [message('/home/test/lib/test.dart', 49, 9)]),
     ]);
   }
 }