diff --git a/test/EFCore.Specification.Tests/Query/GearsOfWarQueryTestBase.cs b/test/EFCore.Specification.Tests/Query/GearsOfWarQueryTestBase.cs
index 424f39c049a..3020bd67816 100644
--- a/test/EFCore.Specification.Tests/Query/GearsOfWarQueryTestBase.cs
+++ b/test/EFCore.Specification.Tests/Query/GearsOfWarQueryTestBase.cs
@@ -7333,6 +7333,17 @@ public virtual Task Byte_array_contains_parameter(bool async)
                 ss => ss.Set<Squad>().Where(s => s.Banner != null && s.Banner.Contains(someByte)));
         }
 
+        [ConditionalTheory]
+        [MemberData(nameof(IsAsyncData))]
+        public virtual Task OrderBy_bool_coming_from_optional_navigation(bool async)
+        {
+            return AssertQuery(
+                async,
+                ss => ss.Set<Weapon>().Select(w => w.SynergyWith).OrderBy(g => g.IsAutomatic),
+                ss => ss.Set<Weapon>().Select(w => w.SynergyWith).OrderBy(g => MaybeScalar<bool>(g, () => g.IsAutomatic)),
+                assertOrder: true);
+        }
+
         protected GearsOfWarContext CreateContext() => Fixture.CreateContext();
 
         protected virtual void ClearLog()
diff --git a/test/EFCore.SqlServer.FunctionalTests/Query/GearsOfWarQuerySqlServerTest.cs b/test/EFCore.SqlServer.FunctionalTests/Query/GearsOfWarQuerySqlServerTest.cs
index b97cd2fc830..1a704e273f4 100644
--- a/test/EFCore.SqlServer.FunctionalTests/Query/GearsOfWarQuerySqlServerTest.cs
+++ b/test/EFCore.SqlServer.FunctionalTests/Query/GearsOfWarQuerySqlServerTest.cs
@@ -7333,6 +7333,17 @@ ELSE CAST(0 AS bit)
 END = CAST(1 AS bit))");
         }
 
+        public override async Task OrderBy_bool_coming_from_optional_navigation(bool async)
+        {
+            await base.OrderBy_bool_coming_from_optional_navigation(async);
+
+            AssertSql(
+                @"SELECT [w0].[Id], [w0].[AmmunitionType], [w0].[IsAutomatic], [w0].[Name], [w0].[OwnerFullName], [w0].[SynergyWithId]
+FROM [Weapons] AS [w]
+LEFT JOIN [Weapons] AS [w0] ON [w].[SynergyWithId] = [w0].[Id]
+ORDER BY [w0].[IsAutomatic]");
+        }
+
         private void AssertSql(params string[] expected)
             => Fixture.TestSqlLoggerFactory.AssertBaseline(expected);
     }