diff --git a/include/swift/AST/DiagnosticsSema.def b/include/swift/AST/DiagnosticsSema.def
index 0b25a26844069..9ce207e558b7c 100644
--- a/include/swift/AST/DiagnosticsSema.def
+++ b/include/swift/AST/DiagnosticsSema.def
@@ -2964,7 +2964,7 @@ ERROR(dynamic_self_non_method,none,
       "%select{global|local}0 function cannot return 'Self'", (bool))
 
 ERROR(dynamic_self_invalid,none,
-      "covariant 'Self' can only appear as the possibly optional type of a "
+      "covariant 'Self' or 'Self?' can only appear as the type of a "
       "property, subscript or method result; did you mean '%0'?", (StringRef))
 ERROR(dynamic_self_in_mutable_property,none,
       "mutable property cannot have covariant 'Self' type", ())
@@ -2973,11 +2973,14 @@ ERROR(dynamic_self_in_stored_property,none,
 ERROR(dynamic_self_in_mutable_subscript,none,
       "mutable subscript cannot have covariant 'Self' type", ())
 ERROR(dynamic_self_invalid_property,none,
-      "covariant 'Self' can only appear at the top level of property type", ())
+      "covariant 'Self' or 'Self?' can only appear at the top level of "
+      "property type", ())
 ERROR(dynamic_self_invalid_subscript,none,
-      "covariant 'Self' can only appear at the top level of subscript element type", ())
+      "covariant 'Self' or 'Self?' can only appear at the top level of "
+      "subscript element type", ())
 ERROR(dynamic_self_invalid_method,none,
-      "covariant 'Self' can only appear at the top level of method result type", ())
+      "covariant 'Self' or 'Self?' can only appear at the top level of "
+      "method result type", ())
 ERROR(dynamic_self_stored_property_init,none,
       "covariant 'Self' type cannot be referenced from a stored property initializer", ())
 ERROR(dynamic_self_default_arg,none,
diff --git a/test/decl/ext/generic.swift b/test/decl/ext/generic.swift
index c5605cc23e776..8843479880b38 100644
--- a/test/decl/ext/generic.swift
+++ b/test/decl/ext/generic.swift
@@ -149,7 +149,7 @@ extension Array where Element == String { }
 extension GenericClass : P3 where T : P3 { }
 
 extension GenericClass where Self : P3 { }
-// expected-error@-1{{covariant 'Self' can only appear as the possibly optional type of a property, subscript or method result; did you mean 'GenericClass'?}} {{30-34=GenericClass}}
+// expected-error@-1{{covariant 'Self' or 'Self?' can only appear as the type of a property, subscript or method result; did you mean 'GenericClass'?}} {{30-34=GenericClass}}
 // expected-error@-2{{'GenericClass<T>' in conformance requirement does not refer to a generic parameter or associated type}}
 
 protocol P4 {
diff --git a/test/decl/func/dynamic_self.swift b/test/decl/func/dynamic_self.swift
index 867facc840f1b..e56003d684b29 100644
--- a/test/decl/func/dynamic_self.swift
+++ b/test/decl/func/dynamic_self.swift
@@ -24,9 +24,9 @@ enum E0 {
 class C0 {
   func f() -> Self { } // okay
 
-  func g(_ ds: Self) { } // expected-error{{covariant 'Self' can only appear as the possibly optional type of a property, subscript or method result; did you mean 'C0'?}}
+  func g(_ ds: Self) { } // expected-error{{covariant 'Self' or 'Self?' can only appear as the type of a property, subscript or method result; did you mean 'C0'?}}
 
-  func h(_ ds: Self) -> Self { } // expected-error{{covariant 'Self' can only appear as the possibly optional type of a property, subscript or method result; did you mean 'C0'?}}
+  func h(_ ds: Self) -> Self { } // expected-error{{covariant 'Self' or 'Self?' can only appear as the type of a property, subscript or method result; did you mean 'C0'?}}
 }
 
 protocol P0 {
diff --git a/test/type/self.swift b/test/type/self.swift
index fc3d2de731e08..4355ae739b07e 100644
--- a/test/type/self.swift
+++ b/test/type/self.swift
@@ -5,7 +5,7 @@ struct S0<T> {
 }
 
 class C0<T> {
-  func foo(_ other: Self) { } // expected-error{{covariant 'Self' can only appear as the possibly optional type of a property, subscript or method result; did you mean 'C0'?}}
+  func foo(_ other: Self) { } // expected-error{{covariant 'Self' or 'Self?' can only appear as the type of a property, subscript or method result; did you mean 'C0'?}}
 }
 
 enum E0<T> {
@@ -47,7 +47,7 @@ final class FinalMario : Mario {
 
 class A<T> {
   typealias _Self = Self
-  // expected-error@-1 {{covariant 'Self' can only appear as the possibly optional type of a property, subscript or method result; did you mean 'A'?}}
+  // expected-error@-1 {{covariant 'Self' or 'Self?' can only appear as the type of a property, subscript or method result; did you mean 'A'?}}
   let b: Int
   required init(a: Int) {
     print("\(Self.self).\(#function)")
@@ -55,7 +55,7 @@ class A<T> {
     b = a
   }
   static func z(n: Self? = nil) {
-    // expected-error@-1 {{covariant 'Self' can only appear as the possibly optional type of a property, subscript or method result; did you mean 'A'?}}
+    // expected-error@-1 {{covariant 'Self' or 'Self?' can only appear as the type of a property, subscript or method result; did you mean 'A'?}}
     print("\(Self.self).\(#function)")
   }
   class func y() {
@@ -130,14 +130,14 @@ class C {
     // expected-warning@-1 {{conditional cast from 'Self' to 'Self' always succeeds}}
   }
   func h(j: () -> Self) -> () -> Self {
-    // expected-error@-1 {{covariant 'Self' can only appear at the top level of method result type}}
+    // expected-error@-1 {{covariant 'Self' or 'Self?' can only appear at the top level of method result type}}
     return { return self }
   }
   func i() -> (Self, Self) {}
-  // expected-error@-1 {{covariant 'Self' can only appear at the top level of method result type}}
+  // expected-error@-1 {{covariant 'Self' or 'Self?' can only appear at the top level of method result type}}
 
   func j() -> Self.Type {}
-  // expected-error@-1 {{covariant 'Self' can only appear at the top level of method result type}}
+  // expected-error@-1 {{covariant 'Self' or 'Self?' can only appear at the top level of method result type}}
 
   let p0: Self? // expected-error {{stored property cannot have covariant 'Self' type}}
   var p1: Self? // expected-error {{stored property cannot have covariant 'Self' type}}