diff --git a/src/Discord.Net.Core/Entities/Channels/IMessageChannel.cs b/src/Discord.Net.Core/Entities/Channels/IMessageChannel.cs
index a1df5b4c7..5a6e5df59 100644
--- a/src/Discord.Net.Core/Entities/Channels/IMessageChannel.cs
+++ b/src/Discord.Net.Core/Entities/Channels/IMessageChannel.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.Collections.Generic;
 using System.IO;
 using System.Threading.Tasks;
@@ -11,10 +11,10 @@ namespace Discord
         Task<IUserMessage> SendMessageAsync(string text, bool isTTS = false, Embed embed = null, RequestOptions options = null);
 #if FILESYSTEM
         /// <summary> Sends a file to this text channel, with an optional caption. </summary>
-        Task<IUserMessage> SendFileAsync(string filePath, string text = null, bool isTTS = false, RequestOptions options = null);
+        Task<IUserMessage> SendFileAsync(string filePath, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null);
 #endif
         /// <summary> Sends a file to this text channel, with an optional caption. </summary>
-        Task<IUserMessage> SendFileAsync(Stream stream, string filename, string text = null, bool isTTS = false, RequestOptions options = null);
+        Task<IUserMessage> SendFileAsync(Stream stream, string filename, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null);
 
         /// <summary> Gets a message from this message channel with the given id, or null if not found. </summary>
         Task<IMessage> GetMessageAsync(ulong id, CacheMode mode = CacheMode.AllowDownload, RequestOptions options = null);
diff --git a/src/Discord.Net.Core/Extensions/UserExtensions.cs b/src/Discord.Net.Core/Extensions/UserExtensions.cs
index eac25391e..863201cfe 100644
--- a/src/Discord.Net.Core/Extensions/UserExtensions.cs
+++ b/src/Discord.Net.Core/Extensions/UserExtensions.cs
@@ -1,4 +1,4 @@
-using System.Threading.Tasks;
+using System.Threading.Tasks;
 using System.IO;
 
 namespace Discord
@@ -8,10 +8,10 @@ namespace Discord
         /// <summary>
         /// Sends a message to the user via DM.
         /// </summary>
-        public static async Task<IUserMessage> SendMessageAsync(this IUser user, 
-            string text, 
+        public static async Task<IUserMessage> SendMessageAsync(this IUser user,
+            string text,
             bool isTTS = false,
-            Embed embed = null, 
+            Embed embed = null,
             RequestOptions options = null)
         {
             return await (await user.GetOrCreateDMChannelAsync().ConfigureAwait(false)).SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
@@ -25,23 +25,25 @@ namespace Discord
             string filename,
             string text = null,
             bool isTTS = false,
+            Embed embed = null,
             RequestOptions options = null
             )
         {
-            return await (await user.GetOrCreateDMChannelAsync().ConfigureAwait(false)).SendFileAsync(stream, filename, text, isTTS, options).ConfigureAwait(false);
+            return await (await user.GetOrCreateDMChannelAsync().ConfigureAwait(false)).SendFileAsync(stream, filename, text, isTTS, embed, options).ConfigureAwait(false);
         }
 
 #if FILESYSTEM
         /// <summary>
         /// Sends a file to the user via DM.
         /// </summary>
-        public static async Task<IUserMessage> SendFileAsync(this IUser user, 
-            string filePath, 
-            string text = null, 
-            bool isTTS = false, 
+        public static async Task<IUserMessage> SendFileAsync(this IUser user,
+            string filePath,
+            string text = null,
+            bool isTTS = false,
+            Embed embed = null,
             RequestOptions options = null)
         {
-            return await (await user.GetOrCreateDMChannelAsync().ConfigureAwait(false)).SendFileAsync(filePath, text, isTTS, options).ConfigureAwait(false);
+            return await (await user.GetOrCreateDMChannelAsync().ConfigureAwait(false)).SendFileAsync(filePath, text, isTTS, embed, options).ConfigureAwait(false);
         }
 #endif
     }
diff --git a/src/Discord.Net.Rest/API/Rest/UploadFileParams.cs b/src/Discord.Net.Rest/API/Rest/UploadFileParams.cs
index 30bfc7f9a..781fc0cfd 100644
--- a/src/Discord.Net.Rest/API/Rest/UploadFileParams.cs
+++ b/src/Discord.Net.Rest/API/Rest/UploadFileParams.cs
@@ -1,18 +1,26 @@
-#pragma warning disable CS1591
+#pragma warning disable CS1591
+using Discord.Net.Converters;
 using Discord.Net.Rest;
+using Newtonsoft.Json;
 using System.Collections.Generic;
+using System.Globalization;
 using System.IO;
+using System.Text;
 
 namespace Discord.API.Rest
 {
     internal class UploadFileParams
     {
+        // Fuckin Discord man.
+        private static JsonSerializer _serializer = new JsonSerializer { ContractResolver = new DiscordContractResolver() };
+
         public Stream File { get; }
 
         public Optional<string> Filename { get; set; }
         public Optional<string> Content { get; set; }
         public Optional<string> Nonce { get; set; }
         public Optional<bool> IsTTS { get; set; }
+        public Optional<Embed> Embed { get; set; }
 
         public UploadFileParams(Stream file)
         {
@@ -29,6 +37,17 @@ namespace Discord.API.Rest
                 d["tts"] = IsTTS.Value.ToString();
             if (Nonce.IsSpecified)
                 d["nonce"] = Nonce.Value;
+            if (Embed.IsSpecified)
+            {
+                var sb = new StringBuilder(256);
+                using (TextWriter text = new StringWriter(sb, CultureInfo.InvariantCulture))
+                using (JsonWriter writer = new JsonTextWriter(text))
+                {
+                    // I apologise for the mess I've created here, god damn is this annoying.
+                    _serializer.Serialize(writer, new Dictionary<string, object>() { { "embed", Embed.Value } });
+                }
+                d["payload_json"] = sb.ToString();
+            }
             return d;
         }
     }
diff --git a/src/Discord.Net.Rest/Entities/Channels/ChannelHelper.cs b/src/Discord.Net.Rest/Entities/Channels/ChannelHelper.cs
index f4b6c7f23..710746896 100644
--- a/src/Discord.Net.Rest/Entities/Channels/ChannelHelper.cs
+++ b/src/Discord.Net.Rest/Entities/Channels/ChannelHelper.cs
@@ -1,4 +1,4 @@
-using Discord.API.Rest;
+using Discord.API.Rest;
 using System;
 using System.Collections.Generic;
 using System.Collections.Immutable;
@@ -170,17 +170,17 @@ namespace Discord.Rest
 
 #if FILESYSTEM
         public static async Task<RestUserMessage> SendFileAsync(IMessageChannel channel, BaseDiscordClient client,
-            string filePath, string text, bool isTTS, RequestOptions options)
+            string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
         {
             string filename = Path.GetFileName(filePath);
             using (var file = File.OpenRead(filePath))
-                return await SendFileAsync(channel, client, file, filename, text, isTTS, options).ConfigureAwait(false);
+                return await SendFileAsync(channel, client, file, filename, text, isTTS, embed, options).ConfigureAwait(false);
         }
 #endif
         public static async Task<RestUserMessage> SendFileAsync(IMessageChannel channel, BaseDiscordClient client,
-            Stream stream, string filename, string text, bool isTTS, RequestOptions options)
+            Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options)
         {
-            var args = new UploadFileParams(stream) { Filename = filename, Content = text, IsTTS = isTTS };
+            var args = new UploadFileParams(stream) { Filename = filename, Content = text, IsTTS = isTTS, Embed = embed?.ToModel() };
             var model = await client.ApiClient.UploadFileAsync(channel.Id, args, options).ConfigureAwait(false);
             return RestUserMessage.Create(client, channel, client.CurrentUser, model);
         }
diff --git a/src/Discord.Net.Rest/Entities/Channels/IRestMessageChannel.cs b/src/Discord.Net.Rest/Entities/Channels/IRestMessageChannel.cs
index 3a104dd9c..8ab6e9819 100644
--- a/src/Discord.Net.Rest/Entities/Channels/IRestMessageChannel.cs
+++ b/src/Discord.Net.Rest/Entities/Channels/IRestMessageChannel.cs
@@ -1,4 +1,4 @@
-using System.Collections.Generic;
+using System.Collections.Generic;
 using System.IO;
 using System.Threading.Tasks;
 
@@ -10,10 +10,10 @@ namespace Discord.Rest
         new Task<RestUserMessage> SendMessageAsync(string text, bool isTTS = false, Embed embed = null, RequestOptions options = null);
 #if FILESYSTEM
         /// <summary> Sends a file to this text channel, with an optional caption. </summary>
-        new Task<RestUserMessage> SendFileAsync(string filePath, string text = null, bool isTTS = false, RequestOptions options = null);
+        new Task<RestUserMessage> SendFileAsync(string filePath, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null);
 #endif
         /// <summary> Sends a file to this text channel, with an optional caption. </summary>
-        new Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text = null, bool isTTS = false, RequestOptions options = null);
+        new Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null);
 
         /// <summary> Gets a message from this message channel with the given id, or null if not found. </summary>
         Task<RestMessage> GetMessageAsync(ulong id, RequestOptions options = null);
diff --git a/src/Discord.Net.Rest/Entities/Channels/RestDMChannel.cs b/src/Discord.Net.Rest/Entities/Channels/RestDMChannel.cs
index d41441967..08acdf32b 100644
--- a/src/Discord.Net.Rest/Entities/Channels/RestDMChannel.cs
+++ b/src/Discord.Net.Rest/Entities/Channels/RestDMChannel.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.Collections.Generic;
 using System.Collections.Immutable;
 using System.Diagnostics;
@@ -37,7 +37,7 @@ namespace Discord.Rest
         public override async Task UpdateAsync(RequestOptions options = null)
         {
             var model = await Discord.ApiClient.GetChannelAsync(Id, options).ConfigureAwait(false);
-            Update(model); 
+            Update(model);
         }
         public Task CloseAsync(RequestOptions options = null)
             => ChannelHelper.DeleteAsync(this, Discord, options);
@@ -66,11 +66,11 @@ namespace Discord.Rest
         public Task<RestUserMessage> SendMessageAsync(string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
             => ChannelHelper.SendMessageAsync(this, Discord, text, isTTS, embed, options);
 #if FILESYSTEM
-        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options);
 #endif
-        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options);
 
         public Task TriggerTypingAsync(RequestOptions options = null)
             => ChannelHelper.TriggerTypingAsync(this, Discord, options);
@@ -122,11 +122,11 @@ namespace Discord.Rest
             => await GetPinnedMessagesAsync(options).ConfigureAwait(false);
 
 #if FILESYSTEM
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(filePath, text, isTTS, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(filePath, text, isTTS, embed, options).ConfigureAwait(false);
 #endif
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(stream, filename, text, isTTS, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options).ConfigureAwait(false);
         async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
         IDisposable IMessageChannel.EnterTypingState(RequestOptions options)
diff --git a/src/Discord.Net.Rest/Entities/Channels/RestGroupChannel.cs b/src/Discord.Net.Rest/Entities/Channels/RestGroupChannel.cs
index aa5c0f7dc..a1868573e 100644
--- a/src/Discord.Net.Rest/Entities/Channels/RestGroupChannel.cs
+++ b/src/Discord.Net.Rest/Entities/Channels/RestGroupChannel.cs
@@ -1,4 +1,4 @@
-using Discord.Audio;
+using Discord.Audio;
 using System;
 using System.Collections.Generic;
 using System.Collections.Immutable;
@@ -19,7 +19,7 @@ namespace Discord.Rest
         public string Name { get; private set; }
 
         public IReadOnlyCollection<RestGroupUser> Users => _users.ToReadOnlyCollection();
-        public IReadOnlyCollection<RestGroupUser> Recipients 
+        public IReadOnlyCollection<RestGroupUser> Recipients
             => _users.Select(x => x.Value).Where(x => x.Id != Discord.CurrentUser.Id).ToReadOnlyCollection(() => _users.Count - 1);
 
         internal RestGroupChannel(BaseDiscordClient discord, ulong id)
@@ -79,11 +79,11 @@ namespace Discord.Rest
         public Task<RestUserMessage> SendMessageAsync(string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
             => ChannelHelper.SendMessageAsync(this, Discord, text, isTTS, embed, options);
 #if FILESYSTEM
-        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options);
 #endif
-        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options);
 
         public Task TriggerTypingAsync(RequestOptions options = null)
             => ChannelHelper.TriggerTypingAsync(this, Discord, options);
@@ -132,11 +132,11 @@ namespace Discord.Rest
             => await GetPinnedMessagesAsync(options).ConfigureAwait(false);
 
 #if FILESYSTEM
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(filePath, text, isTTS, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(filePath, text, isTTS, embed, options).ConfigureAwait(false);
 #endif
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(stream, filename, text, isTTS, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options).ConfigureAwait(false);
         async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
         IDisposable IMessageChannel.EnterTypingState(RequestOptions options)
diff --git a/src/Discord.Net.Rest/Entities/Channels/RestTextChannel.cs b/src/Discord.Net.Rest/Entities/Channels/RestTextChannel.cs
index 9c29624c1..600b197d6 100644
--- a/src/Discord.Net.Rest/Entities/Channels/RestTextChannel.cs
+++ b/src/Discord.Net.Rest/Entities/Channels/RestTextChannel.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.Collections.Generic;
 using System.Diagnostics;
 using System.IO;
@@ -61,11 +61,11 @@ namespace Discord.Rest
         public Task<RestUserMessage> SendMessageAsync(string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
             => ChannelHelper.SendMessageAsync(this, Discord, text, isTTS, embed, options);
 #if FILESYSTEM
-        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options);
 #endif
-        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options);
 
         public Task DeleteMessagesAsync(IEnumerable<IMessage> messages, RequestOptions options = null)
             => ChannelHelper.DeleteMessagesAsync(this, Discord, messages.Select(x => x.Id), options);
@@ -123,18 +123,18 @@ namespace Discord.Rest
             else
                 return AsyncEnumerable.Empty<IReadOnlyCollection<IMessage>>();
         }
-        async Task<IReadOnlyCollection<IMessage>> IMessageChannel.GetPinnedMessagesAsync(RequestOptions options) 
+        async Task<IReadOnlyCollection<IMessage>> IMessageChannel.GetPinnedMessagesAsync(RequestOptions options)
             => await GetPinnedMessagesAsync(options).ConfigureAwait(false);
 
 #if FILESYSTEM
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(filePath, text, isTTS, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(filePath, text, isTTS, embed, options).ConfigureAwait(false);
 #endif
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, RequestOptions options) 
-            => await SendFileAsync(stream, filename, text, isTTS, options).ConfigureAwait(false);
-        async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options) 
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
-        IDisposable IMessageChannel.EnterTypingState(RequestOptions options) 
+        IDisposable IMessageChannel.EnterTypingState(RequestOptions options)
             => EnterTypingState(options);
 
         //IGuildChannel
diff --git a/src/Discord.Net.Rest/Entities/Channels/RpcVirtualMessageChannel.cs b/src/Discord.Net.Rest/Entities/Channels/RpcVirtualMessageChannel.cs
index eb807423f..3b6a68193 100644
--- a/src/Discord.Net.Rest/Entities/Channels/RpcVirtualMessageChannel.cs
+++ b/src/Discord.Net.Rest/Entities/Channels/RpcVirtualMessageChannel.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.Collections.Generic;
 using System.Diagnostics;
 using System.IO;
@@ -21,7 +21,7 @@ namespace Discord.Rest
         {
             return new RestVirtualMessageChannel(discord, id);
         }
-        
+
         public Task<RestMessage> GetMessageAsync(ulong id, RequestOptions options = null)
             => ChannelHelper.GetMessageAsync(this, Discord, id, options);
         public IAsyncEnumerable<IReadOnlyCollection<RestMessage>> GetMessagesAsync(int limit = DiscordConfig.MaxMessagesPerBatch, RequestOptions options = null)
@@ -36,11 +36,11 @@ namespace Discord.Rest
         public Task<RestUserMessage> SendMessageAsync(string text, bool isTTS, Embed embed = null, RequestOptions options = null)
             => ChannelHelper.SendMessageAsync(this, Discord, text, isTTS, embed, options);
 #if FILESYSTEM
-        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options);
 #endif
-        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options);
 
         public Task TriggerTypingAsync(RequestOptions options = null)
             => ChannelHelper.TriggerTypingAsync(this, Discord, options);
@@ -82,11 +82,11 @@ namespace Discord.Rest
             => await GetPinnedMessagesAsync(options);
 
 #if FILESYSTEM
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(filePath, text, isTTS, options);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(filePath, text, isTTS, embed, options);
 #endif
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(stream, filename, text, isTTS, options);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options);
         async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options);
         IDisposable IMessageChannel.EnterTypingState(RequestOptions options)
diff --git a/src/Discord.Net.Rest/Net/DefaultRestClient.cs b/src/Discord.Net.Rest/Net/DefaultRestClient.cs
index 637099fd6..5235352f6 100644
--- a/src/Discord.Net.Rest/Net/DefaultRestClient.cs
+++ b/src/Discord.Net.Rest/Net/DefaultRestClient.cs
@@ -1,4 +1,5 @@
-using Newtonsoft.Json;
+using Discord.Net.Converters;
+using Newtonsoft.Json;
 using System;
 using System.Collections.Generic;
 using System.Globalization;
@@ -35,7 +36,7 @@ namespace Discord.Net.Rest
             SetHeader("accept-encoding", "gzip, deflate");
 
             _cancelToken = CancellationToken.None;
-            _errorDeserializer = new JsonSerializer();
+            _errorDeserializer = new JsonSerializer() { ContractResolver = new DiscordContractResolver() };
         }
         private void Dispose(bool disposing)
         {
diff --git a/src/Discord.Net.WebSocket/Entities/Channels/ISocketMessageChannel.cs b/src/Discord.Net.WebSocket/Entities/Channels/ISocketMessageChannel.cs
index e2119e7a2..026bd8378 100644
--- a/src/Discord.Net.WebSocket/Entities/Channels/ISocketMessageChannel.cs
+++ b/src/Discord.Net.WebSocket/Entities/Channels/ISocketMessageChannel.cs
@@ -1,4 +1,4 @@
-using Discord.Rest;
+using Discord.Rest;
 using System.Collections.Generic;
 using System.IO;
 using System.Threading.Tasks;
@@ -14,10 +14,10 @@ namespace Discord.WebSocket
         new Task<RestUserMessage> SendMessageAsync(string text, bool isTTS = false, Embed embed = null, RequestOptions options = null);
 #if FILESYSTEM
         /// <summary> Sends a file to this text channel, with an optional caption. </summary>
-        new Task<RestUserMessage> SendFileAsync(string filePath, string text = null, bool isTTS = false, RequestOptions options = null);
+        new Task<RestUserMessage> SendFileAsync(string filePath, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null);
 #endif
         /// <summary> Sends a file to this text channel, with an optional caption. </summary>
-        new Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text = null, bool isTTS = false, RequestOptions options = null);
+        new Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null);
 
         SocketMessage GetCachedMessage(ulong id);
         /// <summary> Gets the last N messages from this message channel. </summary>
diff --git a/src/Discord.Net.WebSocket/Entities/Channels/SocketDMChannel.cs b/src/Discord.Net.WebSocket/Entities/Channels/SocketDMChannel.cs
index 00cef60f8..451240e66 100644
--- a/src/Discord.Net.WebSocket/Entities/Channels/SocketDMChannel.cs
+++ b/src/Discord.Net.WebSocket/Entities/Channels/SocketDMChannel.cs
@@ -1,4 +1,4 @@
-using Discord.Rest;
+using Discord.Rest;
 using System;
 using System.Collections.Generic;
 using System.Collections.Immutable;
@@ -70,11 +70,11 @@ namespace Discord.WebSocket
         public Task<RestUserMessage> SendMessageAsync(string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
             => ChannelHelper.SendMessageAsync(this, Discord, text, isTTS, embed, options);
 #if FILESYSTEM
-        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options);
 #endif
-        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options);
 
         public Task TriggerTypingAsync(RequestOptions options = null)
             => ChannelHelper.TriggerTypingAsync(this, Discord, options);
@@ -113,7 +113,7 @@ namespace Discord.WebSocket
 
         //IPrivateChannel
         IReadOnlyCollection<IUser> IPrivateChannel.Recipients => ImmutableArray.Create<IUser>(Recipient);
-        
+
         //IMessageChannel
         async Task<IMessage> IMessageChannel.GetMessageAsync(ulong id, CacheMode mode, RequestOptions options)
         {
@@ -131,11 +131,11 @@ namespace Discord.WebSocket
         async Task<IReadOnlyCollection<IMessage>> IMessageChannel.GetPinnedMessagesAsync(RequestOptions options)
             => await GetPinnedMessagesAsync(options).ConfigureAwait(false);
 #if FILESYSTEM
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(filePath, text, isTTS, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(filePath, text, isTTS, embed, options).ConfigureAwait(false);
 #endif
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(stream, filename, text, isTTS, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options).ConfigureAwait(false);
         async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
         IDisposable IMessageChannel.EnterTypingState(RequestOptions options)
diff --git a/src/Discord.Net.WebSocket/Entities/Channels/SocketGroupChannel.cs b/src/Discord.Net.WebSocket/Entities/Channels/SocketGroupChannel.cs
index 92a93a903..d46c5fc59 100644
--- a/src/Discord.Net.WebSocket/Entities/Channels/SocketGroupChannel.cs
+++ b/src/Discord.Net.WebSocket/Entities/Channels/SocketGroupChannel.cs
@@ -1,4 +1,4 @@
-using Discord.Audio;
+using Discord.Audio;
 using Discord.Rest;
 using System;
 using System.Collections.Concurrent;
@@ -61,7 +61,7 @@ namespace Discord.WebSocket
                 users[models[i].Id] = SocketGroupUser.Create(this, state, models[i]);
             _users = users;
         }
-        
+
         public Task LeaveAsync(RequestOptions options = null)
             => ChannelHelper.DeleteAsync(this, Discord, options);
 
@@ -98,11 +98,11 @@ namespace Discord.WebSocket
         public Task<RestUserMessage> SendMessageAsync(string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
             => ChannelHelper.SendMessageAsync(this, Discord, text, isTTS, embed, options);
 #if FILESYSTEM
-        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options);
 #endif
-        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options);
 
         public Task TriggerTypingAsync(RequestOptions options = null)
             => ChannelHelper.TriggerTypingAsync(this, Discord, options);
@@ -195,11 +195,11 @@ namespace Discord.WebSocket
         async Task<IReadOnlyCollection<IMessage>> IMessageChannel.GetPinnedMessagesAsync(RequestOptions options)
             => await GetPinnedMessagesAsync(options).ConfigureAwait(false);
 #if FILESYSTEM
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(filePath, text, isTTS, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(filePath, text, isTTS, embed, options).ConfigureAwait(false);
 #endif
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(stream, filename, text, isTTS, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options).ConfigureAwait(false);
         async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
         IDisposable IMessageChannel.EnterTypingState(RequestOptions options)
diff --git a/src/Discord.Net.WebSocket/Entities/Channels/SocketTextChannel.cs b/src/Discord.Net.WebSocket/Entities/Channels/SocketTextChannel.cs
index 7b8f572d2..ec7615b55 100644
--- a/src/Discord.Net.WebSocket/Entities/Channels/SocketTextChannel.cs
+++ b/src/Discord.Net.WebSocket/Entities/Channels/SocketTextChannel.cs
@@ -1,4 +1,4 @@
-using Discord.Rest;
+using Discord.Rest;
 using System;
 using System.Collections.Generic;
 using System.Collections.Immutable;
@@ -16,7 +16,7 @@ namespace Discord.WebSocket
         private readonly MessageCache _messages;
 
         public string Topic { get; private set; }
-        
+
         private bool _nsfw;
         public bool IsNsfw => _nsfw || ChannelHelper.IsNsfw(this);
 
@@ -24,9 +24,9 @@ namespace Discord.WebSocket
         public IReadOnlyCollection<SocketMessage> CachedMessages => _messages?.Messages ?? ImmutableArray.Create<SocketMessage>();
         public override IReadOnlyCollection<SocketGuildUser> Users
             => Guild.Users.Where(x => Permissions.GetValue(
-                Permissions.ResolveChannel(Guild, x, this, Permissions.ResolveGuild(Guild, x)), 
+                Permissions.ResolveChannel(Guild, x, this, Permissions.ResolveGuild(Guild, x)),
                 ChannelPermission.ViewChannel)).ToImmutableArray();
-        
+
         internal SocketTextChannel(DiscordSocketClient discord, ulong id, SocketGuild guild)
             : base(discord, id, guild)
         {
@@ -78,11 +78,11 @@ namespace Discord.WebSocket
         public Task<RestUserMessage> SendMessageAsync(string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
             => ChannelHelper.SendMessageAsync(this, Discord, text, isTTS, embed, options);
 #if FILESYSTEM
-        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options);
 #endif
-        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, RequestOptions options = null)
-            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, options);
+        public Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options);
 
         public Task DeleteMessagesAsync(IEnumerable<IMessage> messages, RequestOptions options = null)
             => ChannelHelper.DeleteMessagesAsync(this, Discord, messages.Select(x => x.Id), options);
@@ -155,14 +155,14 @@ namespace Discord.WebSocket
         async Task<IReadOnlyCollection<IMessage>> IMessageChannel.GetPinnedMessagesAsync(RequestOptions options)
             => await GetPinnedMessagesAsync(options).ConfigureAwait(false);
 #if FILESYSTEM
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(filePath, text, isTTS, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(filePath, text, isTTS, embed, options).ConfigureAwait(false);
 #endif
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, RequestOptions options)
-            => await SendFileAsync(stream, filename, text, isTTS, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options).ConfigureAwait(false);
         async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
         IDisposable IMessageChannel.EnterTypingState(RequestOptions options)
             => EnterTypingState(options);
     }
-}
\ No newline at end of file
+}