diff --git a/src/Discord.Net.Core/Net/Converters/DiscordContractResolver.cs b/src/Discord.Net.Core/Net/Converters/DiscordContractResolver.cs
index 3357932d4..e78fe032d 100644
--- a/src/Discord.Net.Core/Net/Converters/DiscordContractResolver.cs
+++ b/src/Discord.Net.Core/Net/Converters/DiscordContractResolver.cs
@@ -28,16 +28,25 @@ namespace Discord.Net.Converters
 
                 if (genericType == typeof(Optional<>))
                 {
-                    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);
-
-                    converter = MakeGenericConverter(propInfo, typeof(OptionalConverter<>), innerTypeOutput);
+                    if (type == typeof(Optional<API.Image?>))
+                    {
+                        converter = ImageConverter.Instance;
+                    }
+                    else
+                    {
+                        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);
+
+                        converter = MakeGenericConverter(propInfo, typeof(OptionalConverter<>), innerTypeOutput);
+                    }
                 }
                 else
                     converter = GetConverter(propInfo, type);
diff --git a/src/Discord.Net.Core/Net/Converters/ImageConverter.cs b/src/Discord.Net.Core/Net/Converters/ImageConverter.cs
index e82b7952b..8cdac09bb 100644
--- a/src/Discord.Net.Core/Net/Converters/ImageConverter.cs
+++ b/src/Discord.Net.Core/Net/Converters/ImageConverter.cs
@@ -20,7 +20,7 @@ namespace Discord.Net.Converters
 
         public override void WriteJson(JsonWriter writer, object value, JsonSerializer serializer)
         {
-            var image = (Model)value;
+            var image = ((Optional<Model?>)value).Value.Value;
 
             if (image.Stream != null)
             {