diff --git a/src/Thinktecture.Runtime.Extensions.EntityFrameworkCore.Sources/EntityFrameworkCore/Storage/ValueConversion/ValueObjectValueConverterFactory.cs b/src/Thinktecture.Runtime.Extensions.EntityFrameworkCore.Sources/EntityFrameworkCore/Storage/ValueConversion/ValueObjectValueConverterFactory.cs
index b0b7c2fa..722fb9e6 100644
--- a/src/Thinktecture.Runtime.Extensions.EntityFrameworkCore.Sources/EntityFrameworkCore/Storage/ValueConversion/ValueObjectValueConverterFactory.cs
+++ b/src/Thinktecture.Runtime.Extensions.EntityFrameworkCore.Sources/EntityFrameworkCore/Storage/ValueConversion/ValueObjectValueConverterFactory.cs
@@ -96,6 +96,11 @@ private static Expression<Func<TKey, T>> GetConverterFromKey<T, TKey>(bool useCo
       return (Expression<Func<TKey, T>>)(factoryMethod ?? throw new InvalidOperationException($"A value converter cannot be created for the type '{typeof(T).Name}' because it has no factory methods."));
    }
 
+   private static T Convert<T>(object value)
+   {
+      return (T)System.Convert.ChangeType(value, typeof(T));
+   }
+
    private sealed class ValueObjectValueConverter<T, TKey> : ValueConverter<T, TKey>
       where T : IValueObjectFactory<TKey>, IValueObjectConvertable<TKey>
       where TKey : notnull
@@ -110,7 +115,8 @@ public ValueObjectValueConverter(bool useConstructor)
          {
             null => null,
             TKey key => key, // useful for comparisons of value objects with its key types
-            _ => ((T)o).ToValue()
+            T obj => obj.ToValue(),
+            _ => Convert<TKey>(o)
          };
       }
    }
@@ -130,13 +136,15 @@ public ValidatableEnumValueConverter(bool validateOnWrite)
                                 {
                                    null => null,
                                    TKey key => key, // useful for comparisons of value objects with its key types
-                                   _ => GetKeyIfValid((TEnum)o)
+                                   TEnum obj => GetKeyIfValid(obj),
+                                   _ => Convert<TKey>(o)
                                 }
                                 : o => o switch
                                 {
                                    null => null,
                                    TKey key => key, // useful for comparisons of value objects with its key types
-                                   _ => ((TEnum)o).ToValue()
+                                   TEnum obj => obj.ToValue(),
+                                   _ => Convert<TKey>(o)
                                 };
       }
 
diff --git a/test/Thinktecture.Runtime.Extensions.EntityFrameworkCore.Tests.Sources/EntityFrameworkCore/ValueConversion/ValueObjectValueConverterFactoryTests.cs b/test/Thinktecture.Runtime.Extensions.EntityFrameworkCore.Tests.Sources/EntityFrameworkCore/ValueConversion/ValueObjectValueConverterFactoryTests.cs
index 153f1383..ac620e84 100644
--- a/test/Thinktecture.Runtime.Extensions.EntityFrameworkCore.Tests.Sources/EntityFrameworkCore/ValueConversion/ValueObjectValueConverterFactoryTests.cs
+++ b/test/Thinktecture.Runtime.Extensions.EntityFrameworkCore.Tests.Sources/EntityFrameworkCore/ValueConversion/ValueObjectValueConverterFactoryTests.cs
@@ -83,9 +83,43 @@ UPDATE TestEntities_with_Enum_and_ValueObjects
    [Fact]
    public async Task Should_not_roundtrip_convert_underlying_type_to_value_object_and_back_to_underlying_type()
    {
+      var item = TestSmartEnum_Struct_IntBased.Value1;
+      TestSmartEnum_Struct_IntBased? nullableItem = item;
+
+      var valueObj = IntBasedStructValueObject.Create(42);
+      IntBasedStructValueObject? nullableValueObj = valueObj;
+
+      long int64 = 42;
+      long? nullableInt64 = int64;
+      int int32 = 42;
+      int? nullableInt32 = int32;
+      short int16 = 42;
+      short? nullableInt16 = int16;
+      decimal deci = 42;
+      decimal? nullableDecimal = deci;
+
       await _ctx.TestEntities_with_Enum_and_ValueObjects
-                .Where(e => e.IntBasedStructValueObject == 42
-                            && e.TestSmartEnum_Struct_IntBased == 42)
+                .Where(e => e.TestSmartEnum_Struct_IntBased == item
+                            && e.TestSmartEnum_Struct_IntBased == nullableItem
+                            && e.IntBasedStructValueObject == valueObj
+                            && e.IntBasedStructValueObject == nullableValueObj
+                            && e.IntBasedStructValueObject == int64
+                            && e.TestSmartEnum_Struct_IntBased == int64
+                            && e.IntBasedStructValueObject == nullableInt64
+                            && e.TestSmartEnum_Struct_IntBased == nullableInt64
+                            && e.IntBasedStructValueObject == int32
+                            && e.TestSmartEnum_Struct_IntBased == int32
+                            && e.IntBasedStructValueObject == nullableInt32
+                            && e.TestSmartEnum_Struct_IntBased == nullableInt32
+                            && e.IntBasedStructValueObject == int16
+                            && e.TestSmartEnum_Struct_IntBased == int16
+                            && e.IntBasedStructValueObject == nullableInt16
+                            && e.TestSmartEnum_Struct_IntBased == nullableInt16
+                            && e.IntBasedStructValueObject == deci
+                            && e.TestSmartEnum_Struct_IntBased == deci
+                            && e.IntBasedStructValueObject == nullableDecimal
+                            && e.TestSmartEnum_Struct_IntBased == nullableDecimal
+                      )
                 .ToListAsync();
    }