diff --git a/pkg/front_end/testcases/general/issue52485.dart b/pkg/front_end/testcases/general/issue52485.dart
new file mode 100644
index 00000000000..e231542e291
--- /dev/null
+++ b/pkg/front_end/testcases/general/issue52485.dart
@@ -0,0 +1,13 @@
+// Copyright (c) 2023, the Dart project authors.  Please see the AUTHORS file
+// for details. All rights reserved. Use of this source code is governed by a
+// BSD-style license that can be found in the LICENSE file.
+
+class A {}
+
+Future<void> h1<X extends Future<A>?>(X x) async {
+  var x2 = await x; // Remains null.
+  print([x2].runtimeType); // 'List<A>`.
+  print(x2); // 'null': A soundness violation.
+}
+
+void main() async => await h1<Null>(null);
diff --git a/pkg/front_end/testcases/general/issue52485.dart.strong.expect b/pkg/front_end/testcases/general/issue52485.dart.strong.expect
new file mode 100644
index 00000000000..a7bf23575fc
--- /dev/null
+++ b/pkg/front_end/testcases/general/issue52485.dart.strong.expect
@@ -0,0 +1,17 @@
+library /*isNonNullableByDefault*/;
+import self as self;
+import "dart:core" as core;
+import "dart:async" as asy;
+
+class A extends core::Object {
+  synthetic constructor •() → self::A
+    : super core::Object::•()
+    ;
+}
+static method h1<X extends asy::Future<self::A>?>(self::h1::X% x) → asy::Future<void> async /* futureValueType= void */ {
+  self::A? x2 = await x /* runtimeCheckType= asy::Future<self::A?> */ ;
+  core::print(<self::A?>[x2].{core::Object::runtimeType}{core::Type});
+  core::print(x2);
+}
+static method main() → void async /* futureValueType= void */ 
+  return await self::h1<Null>(null);
diff --git a/pkg/front_end/testcases/general/issue52485.dart.strong.transformed.expect b/pkg/front_end/testcases/general/issue52485.dart.strong.transformed.expect
new file mode 100644
index 00000000000..3471777bdbc
--- /dev/null
+++ b/pkg/front_end/testcases/general/issue52485.dart.strong.transformed.expect
@@ -0,0 +1,17 @@
+library /*isNonNullableByDefault*/;
+import self as self;
+import "dart:core" as core;
+import "dart:async" as asy;
+
+class A extends core::Object {
+  synthetic constructor •() → self::A
+    : super core::Object::•()
+    ;
+}
+static method h1<X extends asy::Future<self::A>?>(self::h1::X% x) → asy::Future<void> async /* futureValueType= void */ {
+  self::A? x2 = await x /* runtimeCheckType= asy::Future<self::A?> */ ;
+  core::print(core::_GrowableList::_literal1<self::A?>(x2).{core::Object::runtimeType}{core::Type});
+  core::print(x2);
+}
+static method main() → void async /* futureValueType= void */ 
+  return await self::h1<Null>(null);
diff --git a/pkg/front_end/testcases/general/issue52485.dart.textual_outline.expect b/pkg/front_end/testcases/general/issue52485.dart.textual_outline.expect
new file mode 100644
index 00000000000..e7d14fd3383
--- /dev/null
+++ b/pkg/front_end/testcases/general/issue52485.dart.textual_outline.expect
@@ -0,0 +1,4 @@
+class A {}
+
+Future<void> h1<X extends Future<A>?>(X x) async {}
+void main() async => await h1<Null>(null);
diff --git a/pkg/front_end/testcases/general/issue52485.dart.textual_outline_modelled.expect b/pkg/front_end/testcases/general/issue52485.dart.textual_outline_modelled.expect
new file mode 100644
index 00000000000..9ea9b72839e
--- /dev/null
+++ b/pkg/front_end/testcases/general/issue52485.dart.textual_outline_modelled.expect
@@ -0,0 +1,5 @@
+Future<void> h1<X extends Future<A>?>(X x) async {}
+
+class A {}
+
+void main() async => await h1<Null>(null);
diff --git a/pkg/front_end/testcases/general/issue52485.dart.weak.expect b/pkg/front_end/testcases/general/issue52485.dart.weak.expect
new file mode 100644
index 00000000000..a7bf23575fc
--- /dev/null
+++ b/pkg/front_end/testcases/general/issue52485.dart.weak.expect
@@ -0,0 +1,17 @@
+library /*isNonNullableByDefault*/;
+import self as self;
+import "dart:core" as core;
+import "dart:async" as asy;
+
+class A extends core::Object {
+  synthetic constructor •() → self::A
+    : super core::Object::•()
+    ;
+}
+static method h1<X extends asy::Future<self::A>?>(self::h1::X% x) → asy::Future<void> async /* futureValueType= void */ {
+  self::A? x2 = await x /* runtimeCheckType= asy::Future<self::A?> */ ;
+  core::print(<self::A?>[x2].{core::Object::runtimeType}{core::Type});
+  core::print(x2);
+}
+static method main() → void async /* futureValueType= void */ 
+  return await self::h1<Null>(null);
diff --git a/pkg/front_end/testcases/general/issue52485.dart.weak.modular.expect b/pkg/front_end/testcases/general/issue52485.dart.weak.modular.expect
new file mode 100644
index 00000000000..a7bf23575fc
--- /dev/null
+++ b/pkg/front_end/testcases/general/issue52485.dart.weak.modular.expect
@@ -0,0 +1,17 @@
+library /*isNonNullableByDefault*/;
+import self as self;
+import "dart:core" as core;
+import "dart:async" as asy;
+
+class A extends core::Object {
+  synthetic constructor •() → self::A
+    : super core::Object::•()
+    ;
+}
+static method h1<X extends asy::Future<self::A>?>(self::h1::X% x) → asy::Future<void> async /* futureValueType= void */ {
+  self::A? x2 = await x /* runtimeCheckType= asy::Future<self::A?> */ ;
+  core::print(<self::A?>[x2].{core::Object::runtimeType}{core::Type});
+  core::print(x2);
+}
+static method main() → void async /* futureValueType= void */ 
+  return await self::h1<Null>(null);
diff --git a/pkg/front_end/testcases/general/issue52485.dart.weak.outline.expect b/pkg/front_end/testcases/general/issue52485.dart.weak.outline.expect
new file mode 100644
index 00000000000..c912c4fb8c9
--- /dev/null
+++ b/pkg/front_end/testcases/general/issue52485.dart.weak.outline.expect
@@ -0,0 +1,13 @@
+library /*isNonNullableByDefault*/;
+import self as self;
+import "dart:core" as core;
+import "dart:async" as asy;
+
+class A extends core::Object {
+  synthetic constructor •() → self::A
+    ;
+}
+static method h1<X extends asy::Future<self::A>?>(self::h1::X% x) → asy::Future<void> async 
+  ;
+static method main() → void async 
+  ;
diff --git a/pkg/front_end/testcases/general/issue52485.dart.weak.transformed.expect b/pkg/front_end/testcases/general/issue52485.dart.weak.transformed.expect
new file mode 100644
index 00000000000..3471777bdbc
--- /dev/null
+++ b/pkg/front_end/testcases/general/issue52485.dart.weak.transformed.expect
@@ -0,0 +1,17 @@
+library /*isNonNullableByDefault*/;
+import self as self;
+import "dart:core" as core;
+import "dart:async" as asy;
+
+class A extends core::Object {
+  synthetic constructor •() → self::A
+    : super core::Object::•()
+    ;
+}
+static method h1<X extends asy::Future<self::A>?>(self::h1::X% x) → asy::Future<void> async /* futureValueType= void */ {
+  self::A? x2 = await x /* runtimeCheckType= asy::Future<self::A?> */ ;
+  core::print(core::_GrowableList::_literal1<self::A?>(x2).{core::Object::runtimeType}{core::Type});
+  core::print(x2);
+}
+static method main() → void async /* futureValueType= void */ 
+  return await self::h1<Null>(null);
diff --git a/pkg/kernel/lib/type_environment.dart b/pkg/kernel/lib/type_environment.dart
index 5fbd0efcb08..4b1585feeea 100644
--- a/pkg/kernel/lib/type_environment.dart
+++ b/pkg/kernel/lib/type_environment.dart
@@ -129,18 +129,33 @@ abstract class TypeEnvironment extends Types {
       DartType bound = t.right;
       DartType? futureType = _futureTypeOf(bound);
       if (futureType != null) {
-        return _withDeclaredNullability(flatten(futureType), t.nullability);
+        DartType flattenedFutureType = flatten(futureType);
+        return _withDeclaredNullability(flattenedFutureType,
+            uniteNullabilities(t.nullability, flattenedFutureType.nullability));
       } else {
-        return _withDeclaredNullability(flatten(t.left), t.nullability);
+        DartType flattenedFutureType = flatten(t.left);
+        return _withDeclaredNullability(flattenedFutureType,
+            uniteNullabilities(t.nullability, flattenedFutureType.nullability));
       }
     } else {
       DartType? futureType = _futureTypeOf(t);
       if (futureType is InterfaceType) {
         assert(futureType.classNode == coreTypes.futureClass);
+        DartType typeArgument = futureType.typeArguments.single;
         return _withDeclaredNullability(
-            futureType.typeArguments.single, t.nullability);
+            typeArgument,
+            uniteNullabilities(
+                t.nullability,
+                uniteNullabilities(
+                    futureType.nullability, typeArgument.nullability)));
       } else if (futureType is FutureOrType) {
-        return _withDeclaredNullability(futureType.typeArgument, t.nullability);
+        DartType typeArgument = futureType.typeArgument;
+        return _withDeclaredNullability(
+            typeArgument,
+            uniteNullabilities(
+                t.nullability,
+                uniteNullabilities(
+                    futureType.nullability, typeArgument.nullability)));
       } else {
         return t;
       }