diff --git a/src/Discord.Net/Net/Converters/DiscordContractResolver.cs b/src/Discord.Net/Net/Converters/DiscordContractResolver.cs
index be22c9b20..4e3aba41e 100644
--- a/src/Discord.Net/Net/Converters/DiscordContractResolver.cs
+++ b/src/Discord.Net/Net/Converters/DiscordContractResolver.cs
@@ -3,6 +3,7 @@ using Newtonsoft.Json;
 using Newtonsoft.Json.Serialization;
 using System;
 using System.Collections.Generic;
+using System.IO;
 using System.Linq;
 using System.Reflection;
 
@@ -17,59 +18,34 @@ namespace Discord.Net.Converters
         {
             var property = base.CreateProperty(member, memberSerialization);
             var propInfo = member as PropertyInfo;
-
             if (propInfo != null)
             {
-                JsonConverter converter = null;
-                var type = property.PropertyType;
-                var typeInfo = type.GetTypeInfo();
+                JsonConverter converter;
+                var type = propInfo.PropertyType;
 
-                //Primitives
-                if (propInfo.GetCustomAttribute<Int53Attribute>() == null)
+                if (type.IsConstructedGenericType && type.GetGenericTypeDefinition() == typeof(Optional<>))
                 {
-                    if (type == typeof(ulong))
-                        converter = UInt64Converter.Instance;
-                    else if (type == typeof(ulong?))
-                        converter = NullableUInt64Converter.Instance;
-                    else if (typeInfo.ImplementedInterfaces.Any(x => x == typeof(IEnumerable<ulong>)))
-                        converter = UInt64ArrayConverter.Instance;
-                }
-                if (converter == null)
-                { 
-                    //Enums
-                    if (type == typeof(ChannelType))
-                        converter = ChannelTypeConverter.Instance;
-                    else if (type == typeof(PermissionTarget))
-                        converter = PermissionTargetConverter.Instance;
-                    else if (type == typeof(UserStatus))
-                        converter = UserStatusConverter.Instance;
-                    else if (type == typeof(Direction))
-                        converter = DirectionConverter.Instance;
+                    var typeInput = propInfo.DeclaringType;
+                    var innerTypeOutput = type.GenericTypeArguments[0];
 
-                    //Entities
-                    if (typeInfo.ImplementedInterfaces.Any(x => x == typeof(IEntity<ulong>)))
-                        converter = UInt64EntityConverter.Instance;
-                    else if (typeInfo.ImplementedInterfaces.Any(x => x == typeof(IEntity<string>)))
-                        converter = StringEntityConverter.Instance;
+                    var getter = typeof(Func<,>).MakeGenericType(typeInput, type);
+                    var getterDelegate = propInfo.GetMethod.CreateDelegate(getter);
+                    var shouldSerialize = _shouldSerialize.MakeGenericMethod(typeInput, innerTypeOutput);
+                    var shouldSerializeDelegate = (Func<object, Delegate, bool>)shouldSerialize.CreateDelegate(typeof(Func<object, Delegate, bool>));
+                    property.ShouldSerialize = x => shouldSerializeDelegate(x, getterDelegate);
 
-                    //Special
-                    else if (type == typeof(string) && propInfo.GetCustomAttribute<ImageAttribute>() != null)
-                        converter = ImageConverter.Instance;
-                    else if (type.IsConstructedGenericType && type.GetGenericTypeDefinition() == typeof(Optional<>))
+                    var converterType = typeof(OptionalConverter<>).MakeGenericType(innerTypeOutput).GetTypeInfo();
+                    var instanceField = converterType.GetDeclaredField("Instance");
+                    converter = instanceField.GetValue(null) as JsonConverter;
+                    if (converter == null)
                     {
-                        var typeInput = propInfo.DeclaringType;
-                        var innerTypeOutput = type.GenericTypeArguments[0];
-
-                        var getter = typeof(Func<,>).MakeGenericType(typeInput, type);
-                        var getterDelegate = propInfo.GetMethod.CreateDelegate(getter);
-                        var shouldSerialize = _shouldSerialize.MakeGenericMethod(typeInput, innerTypeOutput);
-                        var shouldSerializeDelegate = (Func<object, Delegate, bool>)shouldSerialize.CreateDelegate(typeof(Func<object, Delegate, bool>));
-                        property.ShouldSerialize = x => shouldSerializeDelegate(x, getterDelegate);
-
-                        var converterType = typeof(OptionalConverter<>).MakeGenericType(innerTypeOutput);
-                        converter = converterType.GetTypeInfo().GetDeclaredField("Instance").GetValue(null) as JsonConverter;
+                        var innerConverter = GetConverter(propInfo, innerTypeOutput);
+                        converter = converterType.DeclaredConstructors.FirstOrDefault().Invoke(new object[] { innerConverter }) as JsonConverter;
+                        instanceField.SetValue(null, converter);
                     }
                 }
+                else
+                    converter = GetConverter(propInfo, type);
 
                 if (converter != null)
                 {
@@ -77,10 +53,52 @@ namespace Discord.Net.Converters
                     property.MemberConverter = converter;
                 }
             }
-
             return property;
         }
 
+        private JsonConverter GetConverter(PropertyInfo propInfo, Type type, TypeInfo typeInfo = null)
+        {
+            bool hasInt53 = propInfo.GetCustomAttribute<Int53Attribute>() != null;
+
+            //Primitives
+            if (!hasInt53)
+            {
+                if (type == typeof(ulong))
+                    return UInt64Converter.Instance;
+                if (type == typeof(ulong?))
+                    return NullableUInt64Converter.Instance;
+            }
+
+            //Enums
+            if (type == typeof(ChannelType))
+                return ChannelTypeConverter.Instance;
+            if (type == typeof(PermissionTarget))
+                return PermissionTargetConverter.Instance;
+            if (type == typeof(UserStatus))
+                return UserStatusConverter.Instance;
+            if (type == typeof(Direction))
+                return DirectionConverter.Instance;
+
+            //Special
+            if (type == typeof(Stream) && propInfo.GetCustomAttribute<ImageAttribute>() != null)
+                return ImageConverter.Instance;
+            
+
+            if (typeInfo == null) typeInfo = type.GetTypeInfo();
+
+            //Primitives
+            if (!hasInt53 && typeInfo.ImplementedInterfaces.Any(x => x == typeof(IEnumerable<ulong>)))
+                return UInt64ArrayConverter.Instance;
+
+            //Entities
+            if (typeInfo.ImplementedInterfaces.Any(x => x == typeof(IEntity<ulong>)))
+                return UInt64EntityConverter.Instance;
+            if (typeInfo.ImplementedInterfaces.Any(x => x == typeof(IEntity<string>)))
+                return StringEntityConverter.Instance;
+
+            return null;
+        }
+
         private static bool ShouldSerialize<TOwner, TValue>(object owner, Delegate getter)
         {
             return (getter as Func<TOwner, Optional<TValue>>)((TOwner)owner).IsSpecified;
diff --git a/src/Discord.Net/Net/Converters/ImageConverter.cs b/src/Discord.Net/Net/Converters/ImageConverter.cs
index a40b5bf86..3446d2b2e 100644
--- a/src/Discord.Net/Net/Converters/ImageConverter.cs
+++ b/src/Discord.Net/Net/Converters/ImageConverter.cs
@@ -1,5 +1,4 @@
-using Discord.API;
-using Newtonsoft.Json;
+using Newtonsoft.Json;
 using System;
 using System.IO;
 
@@ -20,8 +19,6 @@ namespace Discord.Net.Converters
 
         public override void WriteJson(JsonWriter writer, object value, JsonSerializer serializer)
         {
-            if (value is Optional<Stream>)
-                value = (Optional<Stream>)value;
             var stream = value as Stream;
 
             byte[] bytes = new byte[stream.Length - stream.Position];
diff --git a/src/Discord.Net/Net/Converters/OptionalConverter.cs b/src/Discord.Net/Net/Converters/OptionalConverter.cs
index a1e7c7543..260d642d4 100644
--- a/src/Discord.Net/Net/Converters/OptionalConverter.cs
+++ b/src/Discord.Net/Net/Converters/OptionalConverter.cs
@@ -5,20 +5,36 @@ namespace Discord.Net.Converters
 {
     public class OptionalConverter<T> : JsonConverter
     {
-        public static readonly OptionalConverter<T> Instance = new OptionalConverter<T>();
+        public static OptionalConverter<T> Instance;
+
+        private readonly JsonConverter _innerConverter;
 
         public override bool CanConvert(Type objectType) => true;
         public override bool CanRead => true;
         public override bool CanWrite => true;
 
+        public OptionalConverter(JsonConverter innerConverter)
+        {
+            _innerConverter = innerConverter;
+        }
+
         public override object ReadJson(JsonReader reader, Type objectType, object existingValue, JsonSerializer serializer)
         {
-            return new Optional<T>(serializer.Deserialize<T>(reader));
+            T obj;
+            if (_innerConverter != null)
+                obj = (T)_innerConverter.ReadJson(reader, typeof(T), null, serializer);
+            else
+                obj = serializer.Deserialize<T>(reader);
+            return new Optional<T>(obj);
         }
 
         public override void WriteJson(JsonWriter writer, object value, JsonSerializer serializer)
         {
-            serializer.Serialize(writer, ((Optional<T>)value).Value);
+            value = ((Optional<T>)value).Value;
+            if (_innerConverter != null)
+                _innerConverter.WriteJson(writer, value, serializer);
+            else
+                serializer.Serialize(writer, value, typeof(T));
         }
     }
 }