diff --git a/src/Compilers/CSharp/Portable/Symbols/AbstractTypeMap.cs b/src/Compilers/CSharp/Portable/Symbols/AbstractTypeMap.cs
index be77e9a27411126e2279778b8d1a31f10fa90937..92ba362e6e0f4515a44c58f5a3aa145179d97ba3 100644
--- a/src/Compilers/CSharp/Portable/Symbols/AbstractTypeMap.cs
+++ b/src/Compilers/CSharp/Portable/Symbols/AbstractTypeMap.cs
@@ -325,12 +325,16 @@ internal ImmutableArray<TypeWithAnnotations> SubstituteTypes(ImmutableArray<Type
 
         /// <summary>
         /// Substitute types, and return the results without duplicates, preserving the original order.
+        /// Note, all occurrences of 'dynamic' in resulting types will be replaced with 'object'.
         /// </summary>
         internal void SubstituteConstraintTypesDistinctWithoutModifiers(
+            TypeParameterSymbol owner,
             ImmutableArray<TypeWithAnnotations> original,
             ArrayBuilder<TypeWithAnnotations> result,
             HashSet<TypeParameterSymbol> ignoreTypesDependentOnTypeParametersOpt)
         {
+            DynamicTypeEraser dynamicEraser = null;
+
             if (original.Length == 0)
             {
                 return;
@@ -341,7 +345,7 @@ internal ImmutableArray<TypeWithAnnotations> SubstituteTypes(ImmutableArray<Type
                 if (ignoreTypesDependentOnTypeParametersOpt == null ||
                     !type.Type.ContainsTypeParameters(ignoreTypesDependentOnTypeParametersOpt))
                 {
-                    result.Add(SubstituteType(type));
+                    result.Add(substituteConstraintType(type));
                 }
             }
             else
@@ -352,7 +356,7 @@ internal ImmutableArray<TypeWithAnnotations> SubstituteTypes(ImmutableArray<Type
                     if (ignoreTypesDependentOnTypeParametersOpt == null ||
                         !type.Type.ContainsTypeParameters(ignoreTypesDependentOnTypeParametersOpt))
                     {
-                        var substituted = SubstituteType(type);
+                        var substituted = substituteConstraintType(type);
 
                         if (!map.TryGetValue(substituted.Type, out int mergeWith))
                         {
@@ -368,6 +372,18 @@ internal ImmutableArray<TypeWithAnnotations> SubstituteTypes(ImmutableArray<Type
 
                 map.Free();
             }
+
+            TypeWithAnnotations substituteConstraintType(TypeWithAnnotations type)
+            {
+                if (dynamicEraser == null)
+                {
+                    dynamicEraser = new DynamicTypeEraser(owner.ContainingAssembly.CorLibrary.GetSpecialType(SpecialType.System_Object));
+                }
+
+                TypeWithAnnotations substituted = SubstituteType(type);
+
+                return substituted.WithTypeAndModifiers(dynamicEraser.EraseDynamic(substituted.Type), substituted.CustomModifiers);
+            }
         }
 
         internal ImmutableArray<TypeParameterSymbol> SubstituteTypeParameters(ImmutableArray<TypeParameterSymbol> original)
diff --git a/src/Compilers/CSharp/Portable/Symbols/ConstraintsHelper.cs b/src/Compilers/CSharp/Portable/Symbols/ConstraintsHelper.cs
index 682889d0f2b5425ef7926bd7deea436315608045..53d97bbfab722a33924f6e3d26123c5bd1393efd 100644
--- a/src/Compilers/CSharp/Portable/Symbols/ConstraintsHelper.cs
+++ b/src/Compilers/CSharp/Portable/Symbols/ConstraintsHelper.cs
@@ -108,7 +108,6 @@ internal static class ConstraintsHelper
 
             NamedTypeSymbol effectiveBaseClass = corLibrary.GetSpecialType(typeParameter.HasValueTypeConstraint ? SpecialType.System_ValueType : SpecialType.System_Object);
             TypeSymbol deducedBaseType = effectiveBaseClass;
-            DynamicTypeEraser dynamicEraser = null;
 
             if (constraintTypes.Length == 0)
             {
@@ -125,15 +124,13 @@ internal static class ConstraintsHelper
                 // interfaces, and filter out any constraint types that cause cycles.
                 foreach (var constraintType in constraintTypes)
                 {
+                    Debug.Assert(!constraintType.Type.ContainsDynamic());
+
                     NamedTypeSymbol constraintEffectiveBase;
                     TypeSymbol constraintDeducedBase;
 
                     switch (constraintType.TypeKind)
                     {
-                        case TypeKind.Dynamic:
-                            Debug.Assert(inherited || currentCompilation == null);
-                            continue;
-
                         case TypeKind.TypeParameter:
                             {
                                 var constraintTypeParameter = (TypeParameterSymbol)constraintType.Type;
@@ -188,35 +185,18 @@ internal static class ConstraintsHelper
                         case TypeKind.Interface:
                         case TypeKind.Class:
                         case TypeKind.Delegate:
-                            NamedTypeSymbol erasedConstraintType;
 
-                            if (inherited || currentCompilation == null)
-                            {
-                                // only inherited constraints may contain dynamic
-                                if (dynamicEraser == null)
-                                {
-                                    dynamicEraser = new DynamicTypeEraser(corLibrary.GetSpecialType(SpecialType.System_Object));
-                                }
-
-                                erasedConstraintType = (NamedTypeSymbol)dynamicEraser.EraseDynamic(constraintType.Type);
-                            }
-                            else
-                            {
-                                Debug.Assert(!constraintType.Type.ContainsDynamic());
-                                Debug.Assert(constraintType.TypeKind != TypeKind.Delegate);
-
-                                erasedConstraintType = (NamedTypeSymbol)constraintType.Type;
-                            }
+                            Debug.Assert(inherited || currentCompilation == null || constraintType.TypeKind != TypeKind.Delegate);
 
                             if (constraintType.Type.IsInterfaceType())
                             {
-                                AddInterface(interfacesBuilder, erasedConstraintType);
+                                AddInterface(interfacesBuilder, (NamedTypeSymbol)constraintType.Type);
                                 constraintTypesBuilder.Add(constraintType);
                                 continue;
                             }
                             else
                             {
-                                constraintEffectiveBase = erasedConstraintType;
+                                constraintEffectiveBase = (NamedTypeSymbol)constraintType.Type;
                                 constraintDeducedBase = constraintType.Type;
                                 break;
                             }
@@ -920,7 +900,7 @@ private static bool HasDuplicateInterfaces(NamedTypeSymbol type, ConsList<TypeSy
             // original definition of the type parameters using the map from the constructed symbol.
             var constraintTypes = ArrayBuilder<TypeWithAnnotations>.GetInstance();
             HashSet<DiagnosticInfo> useSiteDiagnostics = null;
-            substitution.SubstituteConstraintTypesDistinctWithoutModifiers(typeParameter.ConstraintTypesWithDefinitionUseSiteDiagnostics(ref useSiteDiagnostics), constraintTypes,
+            substitution.SubstituteConstraintTypesDistinctWithoutModifiers(typeParameter, typeParameter.ConstraintTypesWithDefinitionUseSiteDiagnostics(ref useSiteDiagnostics), constraintTypes,
                                                                  ignoreTypeConstraintsDependentOnTypeParametersOpt);
 
             bool hasError = false;
diff --git a/src/Compilers/CSharp/Portable/Symbols/SubstitutedTypeParameterSymbol.cs b/src/Compilers/CSharp/Portable/Symbols/SubstitutedTypeParameterSymbol.cs
index d4271f503b255927051460cbd10376bc9018a39a..6e70af594e8dd565b674786273b4be6c1a3464d6 100644
--- a/src/Compilers/CSharp/Portable/Symbols/SubstitutedTypeParameterSymbol.cs
+++ b/src/Compilers/CSharp/Portable/Symbols/SubstitutedTypeParameterSymbol.cs
@@ -100,7 +100,7 @@ public override ImmutableArray<CSharpAttributeData> GetAttributes()
         internal override ImmutableArray<TypeWithAnnotations> GetConstraintTypes(ConsList<TypeParameterSymbol> inProgress)
         {
             var constraintTypes = ArrayBuilder<TypeWithAnnotations>.GetInstance();
-            _map.SubstituteConstraintTypesDistinctWithoutModifiers(_underlyingTypeParameter.GetConstraintTypes(inProgress), constraintTypes, null);
+            _map.SubstituteConstraintTypesDistinctWithoutModifiers(_underlyingTypeParameter, _underlyingTypeParameter.GetConstraintTypes(inProgress), constraintTypes, null);
 
             TypeWithAnnotations bestObjectConstraint = default;
 
@@ -160,7 +160,7 @@ internal override ImmutableArray<TypeWithAnnotations> GetConstraintTypes(ConsLis
                 else if (!HasNotNullConstraint && !HasValueTypeConstraint && !HasReferenceTypeConstraint)
                 {
                     var constraintTypes = ArrayBuilder<TypeWithAnnotations>.GetInstance();
-                    _map.SubstituteConstraintTypesDistinctWithoutModifiers(_underlyingTypeParameter.GetConstraintTypes(ConsList<TypeParameterSymbol>.Empty), constraintTypes, null);
+                    _map.SubstituteConstraintTypesDistinctWithoutModifiers(_underlyingTypeParameter, _underlyingTypeParameter.GetConstraintTypes(ConsList<TypeParameterSymbol>.Empty), constraintTypes, null);
                     return IsNotNullableIfReferenceTypeFromConstraintTypes(constraintTypes.ToImmutableAndFree());
                 }
 
diff --git a/src/Compilers/CSharp/Test/Semantic/Semantics/NullableReferenceTypesTests.cs b/src/Compilers/CSharp/Test/Semantic/Semantics/NullableReferenceTypesTests.cs
index e23407cd7e3c035145e1ee4dd4d482a5a4770154..e700958e54ff90f11d4f0af1e8cae40c3528278d 100644
--- a/src/Compilers/CSharp/Test/Semantic/Semantics/NullableReferenceTypesTests.cs
+++ b/src/Compilers/CSharp/Test/Semantic/Semantics/NullableReferenceTypesTests.cs
@@ -70210,6 +70210,219 @@ void symbolValidator(ModuleSymbol m)
             }
         }
 
+        [Fact]
+        public void DynamicConstraint_01()
+        {
+            var source =
+@"
+class B<S>
+{
+    public static void F1<T1>(T1 t1) where T1 : dynamic
+    {
+    }
+
+    public static void F2<T2>(T2 t2) where T2 : B<dynamic>
+    {
+    }
+}";
+            var comp = CreateCompilation(new[] { source });
+            comp.VerifyDiagnostics(
+                // (4,49): error CS1967: Constraint cannot be the dynamic type
+                //     public static void F1<T1>(T1 t1) where T1 : dynamic
+                Diagnostic(ErrorCode.ERR_DynamicTypeAsBound, "dynamic").WithLocation(4, 49),
+                // (8,49): error CS1968: Constraint cannot be a dynamic type 'B<dynamic>'
+                //     public static void F2<T2>(T2 t2) where T2 : B<dynamic>
+                Diagnostic(ErrorCode.ERR_ConstructedDynamicTypeAsBound, "B<dynamic>").WithArguments("B<dynamic>").WithLocation(8, 49)
+                );
+
+            var m = comp.SourceModule;
+
+            var f1 = (MethodSymbol)m.GlobalNamespace.GetMember("B.F1");
+            Assert.Equal("void B<S>.F1<T1>(T1 t1)", f1.ToDisplayString(SymbolDisplayFormat.TestFormatWithConstraints));
+
+            var f2 = (MethodSymbol)m.GlobalNamespace.GetMember("B.F2");
+            Assert.Equal("void B<S>.F2<T2>(T2 t2)", f2.ToDisplayString(SymbolDisplayFormat.TestFormatWithConstraints));
+        }
+
+        [Fact]
+        [WorkItem(36276, "https://github.com/dotnet/roslyn/issues/36276")]
+        public void DynamicConstraint_02()
+        {
+            var source1 =
+ @"
+#nullable enable
+class Test1<T>
+{
+    public virtual void M1<S>() where S : T
+    {
+    }
+}
+
+class Test2 : Test1<dynamic>
+{
+    public override void M1<S>()
+    {
+    }
+
+    void Test()
+    {
+        base.M1<object?>();
+        this.M1<object?>();
+    }
+}
+";
+            var comp1 = CreateCompilation(new[] { source1 });
+            comp1.VerifyDiagnostics(
+                // (18,9): warning CS8631: The type 'object?' cannot be used as type parameter 'S' in the generic type or method 'Test1<dynamic>.M1<S>()'. Nullability of type argument 'object?' doesn't match constraint type 'object'.
+                //         base.M1<object?>();
+                Diagnostic(ErrorCode.WRN_NullabilityMismatchInTypeParameterConstraint, "base.M1<object?>").WithArguments("Test1<dynamic>.M1<S>()", "object", "S", "object?").WithLocation(18, 9),
+                // (19,9): warning CS8631: The type 'object?' cannot be used as type parameter 'S' in the generic type or method 'Test2.M1<S>()'. Nullability of type argument 'object?' doesn't match constraint type 'object'.
+                //         this.M1<object?>();
+                Diagnostic(ErrorCode.WRN_NullabilityMismatchInTypeParameterConstraint, "this.M1<object?>").WithArguments("Test2.M1<S>()", "object", "S", "object?").WithLocation(19, 9)
+                );
+
+            CompileAndVerify(comp1, sourceSymbolValidator: symbolValidator, symbolValidator: symbolValidator);
+            void symbolValidator(ModuleSymbol m)
+            {
+                var m1 = (MethodSymbol)m.GlobalNamespace.GetMember("Test2.M1");
+                Assert.Equal("void Test2.M1<S>() where S : System.Object!", m1.ToDisplayString(SymbolDisplayFormat.TestFormatWithConstraints));
+                Assert.True(m1.TypeParameters[0].IsNotNullableIfReferenceType);
+
+                var baseM1 = m1.OverriddenMethod;
+                Assert.Equal("void Test1<dynamic!>.M1<S>() where S : System.Object!", baseM1.ToDisplayString(SymbolDisplayFormat.TestFormatWithConstraints));
+                Assert.True(baseM1.TypeParameters[0].IsNotNullableIfReferenceType);
+            }
+        }
+
+        [Fact]
+        [WorkItem(36276, "https://github.com/dotnet/roslyn/issues/36276")]
+        public void DynamicConstraint_03()
+        {
+            var source1 =
+ @"
+#nullable disable
+class Test1<T>
+{
+    public virtual void M1<S>() where S : T
+    {
+    }
+}
+
+class Test2 : Test1<dynamic>
+{
+    public override void M1<S>()
+    {
+    }
+
+    void Test()
+    {
+#nullable enable
+        base.M1<object?>();
+        this.M1<object?>();
+    }
+}
+";
+            var comp1 = CreateCompilation(new[] { source1 });
+            comp1.VerifyDiagnostics();
+
+            CompileAndVerify(comp1, sourceSymbolValidator: symbolValidator, symbolValidator: symbolValidator);
+            void symbolValidator(ModuleSymbol m)
+            {
+                var m1 = (MethodSymbol)m.GlobalNamespace.GetMember("Test2.M1");
+                Assert.Equal("void Test2.M1<S>()", m1.ToDisplayString(SymbolDisplayFormat.TestFormatWithConstraints));
+                Assert.Null(m1.TypeParameters[0].IsNotNullableIfReferenceType);
+
+                var baseM1 = m1.OverriddenMethod;
+                Assert.Equal("void Test1<dynamic>.M1<S>()", baseM1.ToDisplayString(SymbolDisplayFormat.TestFormatWithConstraints));
+                Assert.Null(baseM1.TypeParameters[0].IsNotNullableIfReferenceType);
+            }
+        }
+
+        [Fact]
+        public void DynamicConstraint_04()
+        {
+            var source1 =
+ @"
+#nullable enable
+class Test1<T>
+{
+    public virtual void M1<S>() where S : T
+    {
+    }
+}
+
+class Test2 : Test1<Test1<dynamic>>
+{
+    public override void M1<S>()
+    {
+    }
+
+    void Test()
+    {
+        base.M1<Test1<object?>>();
+        this.M1<Test1<object?>>();
+    }
+}
+";
+            var comp1 = CreateCompilation(new[] { source1 });
+            comp1.VerifyDiagnostics(
+                // (18,9): warning CS8631: The type 'Test1<object?>' cannot be used as type parameter 'S' in the generic type or method 'Test1<Test1<dynamic>>.M1<S>()'. Nullability of type argument 'Test1<object?>' doesn't match constraint type 'Test1<object>'.
+                //         base.M1<Test1<object?>>();
+                Diagnostic(ErrorCode.WRN_NullabilityMismatchInTypeParameterConstraint, "base.M1<Test1<object?>>").WithArguments("Test1<Test1<dynamic>>.M1<S>()", "Test1<object>", "S", "Test1<object?>").WithLocation(18, 9),
+                // (19,9): warning CS8631: The type 'Test1<object?>' cannot be used as type parameter 'S' in the generic type or method 'Test2.M1<S>()'. Nullability of type argument 'Test1<object?>' doesn't match constraint type 'Test1<object>'.
+                //         this.M1<Test1<object?>>();
+                Diagnostic(ErrorCode.WRN_NullabilityMismatchInTypeParameterConstraint, "this.M1<Test1<object?>>").WithArguments("Test2.M1<S>()", "Test1<object>", "S", "Test1<object?>").WithLocation(19, 9)
+                );
+
+            CompileAndVerify(comp1, sourceSymbolValidator: symbolValidator, symbolValidator: symbolValidator);
+            void symbolValidator(ModuleSymbol m)
+            {
+                var m1 = (MethodSymbol)m.GlobalNamespace.GetMember("Test2.M1");
+                Assert.Equal("void Test2.M1<S>() where S : Test1<System.Object!>!", m1.ToDisplayString(SymbolDisplayFormat.TestFormatWithConstraints));
+                Assert.True(m1.TypeParameters[0].IsNotNullableIfReferenceType);
+
+                var baseM1 = m1.OverriddenMethod;
+                Assert.Equal("void Test1<Test1<dynamic!>!>.M1<S>() where S : Test1<System.Object!>!", baseM1.ToDisplayString(SymbolDisplayFormat.TestFormatWithConstraints));
+                Assert.True(baseM1.TypeParameters[0].IsNotNullableIfReferenceType);
+            }
+        }
+
+        [Fact]
+        public void DynamicConstraint_05()
+        {
+            var source1 =
+ @"
+#nullable enable
+public class Test1<T>
+{
+    public virtual void M1<S>(S x) where S : I1?, T {}
+}
+
+public interface I1 {}
+
+public class Test2 : Test1<dynamic>
+{
+    public override void M1<S>(S x)
+    {
+    }
+}
+";
+            var comp1 = CreateCompilation(new[] { source1 });
+            comp1.VerifyDiagnostics();
+
+            CompileAndVerify(comp1, sourceSymbolValidator: symbolValidator, symbolValidator: symbolValidator);
+            void symbolValidator(ModuleSymbol m)
+            {
+                var m1 = (MethodSymbol)m.GlobalNamespace.GetMember("Test2.M1");
+                Assert.Equal("void Test2.M1<S>(S x) where S : System.Object!, I1?", m1.ToDisplayString(SymbolDisplayFormat.TestFormatWithConstraints));
+                Assert.True(m1.TypeParameters[0].IsNotNullableIfReferenceType);
+
+                var baseM1 = m1.OverriddenMethod;
+                Assert.Equal("void Test1<dynamic!>.M1<S>(S x) where S : System.Object!, I1?", baseM1.ToDisplayString(SymbolDisplayFormat.TestFormatWithConstraints));
+                Assert.True(baseM1.TypeParameters[0].IsNotNullableIfReferenceType);
+            }
+        }
+
         [Fact]
         public void NotNullConstraint_01()
         {