diff --git a/src/Discord.Net/Entities/Messages/Direction.cs b/src/Discord.Net/Entities/Messages/Direction.cs
index c849146ff..5d8d5e621 100644
--- a/src/Discord.Net/Entities/Messages/Direction.cs
+++ b/src/Discord.Net/Entities/Messages/Direction.cs
@@ -3,6 +3,7 @@
     public enum Direction
     {
         Before,
-        After
+        After,
+        Around
     }
 }
diff --git a/src/Discord.Net/Net/Converters/DirectionConverter.cs b/src/Discord.Net/Net/Converters/DirectionConverter.cs
new file mode 100644
index 000000000..899bd880c
--- /dev/null
+++ b/src/Discord.Net/Net/Converters/DirectionConverter.cs
@@ -0,0 +1,47 @@
+using Newtonsoft.Json;
+using System;
+
+namespace Discord.Net.Converters
+{
+    public class DirectionConverter : JsonConverter
+    {
+        public static readonly DirectionConverter Instance = new DirectionConverter();
+
+        public override bool CanConvert(Type objectType) => true;
+        public override bool CanRead => true;
+        public override bool CanWrite => true;
+
+        public override object ReadJson(JsonReader reader, Type objectType, object existingValue, JsonSerializer serializer)
+        {
+            switch ((string)reader.Value)
+            {
+                case "before":
+                    return Direction.Before;
+                case "after":
+                    return Direction.After;
+                case "around":
+                    return Direction.Around;
+                default:
+                    throw new JsonSerializationException("Unknown direction");
+            }
+        }
+
+        public override void WriteJson(JsonWriter writer, object value, JsonSerializer serializer)
+        {
+            switch ((Direction)value)
+            {
+                case Direction.Before:
+                    writer.WriteValue("before");
+                    break;
+                case Direction.After:
+                    writer.WriteValue("after");
+                    break;
+                case Direction.Around:
+                    writer.WriteValue("around");
+                    break;
+                default:
+                    throw new JsonSerializationException("Invalid direction");
+            }
+        }
+    }
+}
diff --git a/src/Discord.Net/Net/Converters/DiscordContractResolver.cs b/src/Discord.Net/Net/Converters/DiscordContractResolver.cs
index 256afe866..be22c9b20 100644
--- a/src/Discord.Net/Net/Converters/DiscordContractResolver.cs
+++ b/src/Discord.Net/Net/Converters/DiscordContractResolver.cs
@@ -43,6 +43,8 @@ namespace Discord.Net.Converters
                         converter = PermissionTargetConverter.Instance;
                     else if (type == typeof(UserStatus))
                         converter = UserStatusConverter.Instance;
+                    else if (type == typeof(Direction))
+                        converter = DirectionConverter.Instance;
 
                     //Entities
                     if (typeInfo.ImplementedInterfaces.Any(x => x == typeof(IEntity<ulong>)))