diff --git a/src/Discord.Net.Core/Entities/Channels/IMessageChannel.cs b/src/Discord.Net.Core/Entities/Channels/IMessageChannel.cs
index 0e7df3f7c..b5aa69d55 100644
--- a/src/Discord.Net.Core/Entities/Channels/IMessageChannel.cs
+++ b/src/Discord.Net.Core/Entities/Channels/IMessageChannel.cs
@@ -54,11 +54,12 @@ namespace Discord
         /// <param name="isTTS">Whether the message should be read aloud by Discord or not.</param>
         /// <param name="embed">The <see cref="Discord.EmbedType.Rich" /> <see cref="Embed" /> to be sent.</param>
         /// <param name="options">The options to be used when sending the request.</param>
+        /// <param name="isSpoiler">Whether the message attachment should be hidden as a spoiler.</param>
         /// <returns>
         ///     A task that represents an asynchronous send operation for delivering the message. The task result
         ///     contains the sent message.
         /// </returns>
-        Task<IUserMessage> SendFileAsync(string filePath, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null);
+        Task<IUserMessage> SendFileAsync(string filePath, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false);
         /// <summary>
         ///     Sends a file to this message channel with an optional caption.
         /// </summary>
@@ -82,11 +83,12 @@ namespace Discord
         /// <param name="isTTS">Whether the message should be read aloud by Discord or not.</param>
         /// <param name="embed">The <see cref="Discord.EmbedType.Rich"/> <see cref="Embed"/> to be sent.</param>
         /// <param name="options">The options to be used when sending the request.</param>
+        /// <param name="isSpoiler">Whether the message attachment should be hidden as a spoiler.</param>
         /// <returns>
         ///     A task that represents an asynchronous send operation for delivering the message. The task result
         ///     contains the sent message.
         /// </returns>
-        Task<IUserMessage> SendFileAsync(Stream stream, string filename, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null);
+        Task<IUserMessage> SendFileAsync(Stream stream, string filename, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false);
 
         /// <summary>
         ///     Gets a message from this message channel.
diff --git a/src/Discord.Net.Core/Extensions/AttachmentExtensions.cs b/src/Discord.Net.Core/Extensions/AttachmentExtensions.cs
new file mode 100644
index 000000000..605410769
--- /dev/null
+++ b/src/Discord.Net.Core/Extensions/AttachmentExtensions.cs
@@ -0,0 +1,15 @@
+namespace Discord
+{
+    public static class AttachmentExtensions
+    {
+        /// <summary>
+        ///     The prefix applied to files to indicate that it is a spoiler.
+        /// </summary>
+        public const string SpoilerPrefix = "SPOILER_";
+        /// <summary>
+        ///     Gets whether the message's attachments are spoilers or not.
+        /// </summary>
+        public static bool IsSpoiler(this IAttachment attachment)
+            => attachment.Filename.StartsWith(SpoilerPrefix);
+    }
+}
diff --git a/src/Discord.Net.Core/Format.cs b/src/Discord.Net.Core/Format.cs
index fec9b607a..07a9ec75c 100644
--- a/src/Discord.Net.Core/Format.cs
+++ b/src/Discord.Net.Core/Format.cs
@@ -4,7 +4,7 @@ namespace Discord
     public static class Format
     {
         // Characters which need escaping
-        private static readonly string[] SensitiveCharacters = { "\\", "*", "_", "~", "`" };
+        private static readonly string[] SensitiveCharacters = { "\\", "*", "_", "~", "`", "|" };
 
         /// <summary> Returns a markdown-formatted string with bold formatting. </summary>
         public static string Bold(string text) => $"**{text}**";
@@ -14,6 +14,8 @@ namespace Discord
         public static string Underline(string text) => $"__{text}__";
         /// <summary> Returns a markdown-formatted string with strikethrough formatting. </summary>
         public static string Strikethrough(string text) => $"~~{text}~~";
+        /// <summary> Returns a string with spoiler formatting. </summary>
+        public static string Spoiler(string text) => $"||{text}||";
         /// <summary> Returns a markdown-formatted URL. Only works in <see cref="EmbedBuilder"/> descriptions and fields. </summary>
         public static string Url(string text, string url) => $"[{text}]({url})";
         /// <summary> Escapes a URL so that a preview is not generated. </summary>
diff --git a/src/Discord.Net.Rest/API/Rest/UploadFileParams.cs b/src/Discord.Net.Rest/API/Rest/UploadFileParams.cs
index ae15aa5df..7ba21d012 100644
--- a/src/Discord.Net.Rest/API/Rest/UploadFileParams.cs
+++ b/src/Discord.Net.Rest/API/Rest/UploadFileParams.cs
@@ -19,6 +19,7 @@ namespace Discord.API.Rest
         public Optional<string> Nonce { get; set; }
         public Optional<bool> IsTTS { get; set; }
         public Optional<Embed> Embed { get; set; }
+        public bool IsSpoiler { get; set; } = false;
 
         public UploadFileParams(Stream file)
         {
@@ -28,7 +29,10 @@ namespace Discord.API.Rest
         public IReadOnlyDictionary<string, object> ToDictionary()
         {
             var d = new Dictionary<string, object>();
-            d["file"] = new MultipartFile(File, Filename.GetValueOrDefault("unknown.dat"));
+            var filename = Filename.GetValueOrDefault("unknown.dat");
+            if (IsSpoiler && !filename.StartsWith(AttachmentExtensions.SpoilerPrefix))
+                filename = filename.Insert(0, AttachmentExtensions.SpoilerPrefix);
+            d["file"] = new MultipartFile(File, filename);
 
             var payload = new Dictionary<string, object>();
             if (Content.IsSpecified)
@@ -39,6 +43,8 @@ namespace Discord.API.Rest
                 payload["nonce"] = Nonce.Value;
             if (Embed.IsSpecified)
                 payload["embed"] = Embed.Value;
+            if (IsSpoiler)
+                payload["hasSpoiler"] = IsSpoiler.ToString();
 
             var json = new StringBuilder();
             using (var text = new StringWriter(json))
diff --git a/src/Discord.Net.Rest/API/Rest/UploadWebhookFileParams.cs b/src/Discord.Net.Rest/API/Rest/UploadWebhookFileParams.cs
index 479a7857a..26153c21b 100644
--- a/src/Discord.Net.Rest/API/Rest/UploadWebhookFileParams.cs
+++ b/src/Discord.Net.Rest/API/Rest/UploadWebhookFileParams.cs
@@ -22,6 +22,8 @@ namespace Discord.API.Rest
         public Optional<string> AvatarUrl { get; set; }
         public Optional<Embed[]> Embeds { get; set; }
 
+        public bool IsSpoiler { get; set; } = false;
+
         public UploadWebhookFileParams(Stream file)
         {
             File = file;
@@ -30,7 +32,11 @@ namespace Discord.API.Rest
         public IReadOnlyDictionary<string, object> ToDictionary()
         {
             var d = new Dictionary<string, object>();
-            d["file"] = new MultipartFile(File, Filename.GetValueOrDefault("unknown.dat"));
+            var filename = Filename.GetValueOrDefault("unknown.dat");
+            if (IsSpoiler && !filename.StartsWith(AttachmentExtensions.SpoilerPrefix))
+                filename = filename.Insert(0, AttachmentExtensions.SpoilerPrefix);
+
+            d["file"] = new MultipartFile(File, filename);
 
             var payload = new Dictionary<string, object>();
             if (Content.IsSpecified)
diff --git a/src/Discord.Net.Rest/Entities/Channels/ChannelHelper.cs b/src/Discord.Net.Rest/Entities/Channels/ChannelHelper.cs
index d8a97e85a..5fb150cda 100644
--- a/src/Discord.Net.Rest/Entities/Channels/ChannelHelper.cs
+++ b/src/Discord.Net.Rest/Entities/Channels/ChannelHelper.cs
@@ -199,18 +199,18 @@ namespace Discord.Rest
         /// <exception cref="IOException">An I/O error occurred while opening the file.</exception>
         /// <exception cref="ArgumentOutOfRangeException">Message content is too long, length must be less or equal to <see cref="DiscordConfig.MaxMessageSize"/>.</exception>
         public static async Task<RestUserMessage> SendFileAsync(IMessageChannel channel, BaseDiscordClient client,
-            string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
+            string filePath, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
         {
             string filename = Path.GetFileName(filePath);
             using (var file = File.OpenRead(filePath))
-                return await SendFileAsync(channel, client, file, filename, text, isTTS, embed, options).ConfigureAwait(false);
+                return await SendFileAsync(channel, client, file, filename, text, isTTS, embed, options, isSpoiler).ConfigureAwait(false);
         }
 
         /// <exception cref="ArgumentOutOfRangeException">Message content is too long, length must be less or equal to <see cref="DiscordConfig.MaxMessageSize"/>.</exception>
         public static async Task<RestUserMessage> SendFileAsync(IMessageChannel channel, BaseDiscordClient client,
-            Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options)
+            Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
         {
-            var args = new UploadFileParams(stream) { Filename = filename, Content = text, IsTTS = isTTS, Embed = embed != null ? embed.ToModel() : Optional<API.Embed>.Unspecified };
+            var args = new UploadFileParams(stream) { Filename = filename, Content = text, IsTTS = isTTS, Embed = embed != null ? embed.ToModel() : Optional<API.Embed>.Unspecified, IsSpoiler = isSpoiler };
             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 204546cf3..b5ebe8ec4 100644
--- a/src/Discord.Net.Rest/Entities/Channels/IRestMessageChannel.cs
+++ b/src/Discord.Net.Rest/Entities/Channels/IRestMessageChannel.cs
@@ -42,12 +42,12 @@ namespace Discord.Rest
         ///     A task that represents an asynchronous send operation for delivering the message. The task result
         ///     contains the sent message.
         /// </returns>
-        new Task<RestUserMessage> SendFileAsync(string filePath, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null);
+        new Task<RestUserMessage> SendFileAsync(string filePath, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false);
         /// <summary>
         ///     Sends a file to this message channel with an optional caption.
         /// </summary>
         /// <remarks>
-        ///     This method follows the same behavior as described in <see cref="IMessageChannel.SendFileAsync(Stream, string, string, bool, Embed, RequestOptions)"/>.
+        ///     This method follows the same behavior as described in <see cref="IMessageChannel.SendFileAsync(Stream, string, string, bool, Embed, RequestOptions, bool)"/>.
         ///     Please visit its documentation for more details on this method.
         /// </remarks>
         /// <param name="stream">The <see cref="Stream" /> of the file to be sent.</param>
@@ -60,7 +60,7 @@ namespace Discord.Rest
         ///     A task that represents an asynchronous send operation for delivering the message. The task result
         ///     contains the sent message.
         /// </returns>
-        new Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null);
+        new Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false);
 
         /// <summary>
         ///     Gets a message from this message channel.
diff --git a/src/Discord.Net.Rest/Entities/Channels/RestDMChannel.cs b/src/Discord.Net.Rest/Entities/Channels/RestDMChannel.cs
index bee096273..446410b70 100644
--- a/src/Discord.Net.Rest/Entities/Channels/RestDMChannel.cs
+++ b/src/Discord.Net.Rest/Entities/Channels/RestDMChannel.cs
@@ -121,12 +121,12 @@ namespace Discord.Rest
         /// <exception cref="NotSupportedException"><paramref name="filePath" /> is in an invalid format.</exception>
         /// <exception cref="IOException">An I/O error occurred while opening the file.</exception>
         /// <exception cref="ArgumentOutOfRangeException">Message content is too long, length must be less or equal to <see cref="DiscordConfig.MaxMessageSize"/>.</exception>
-        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);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options, isSpoiler);
         /// <inheritdoc />
         /// <exception cref="ArgumentOutOfRangeException">Message content is too long, length must be less or equal to <see cref="DiscordConfig.MaxMessageSize"/>.</exception>
-        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<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options, isSpoiler);
 
         /// <inheritdoc />
         public Task DeleteMessageAsync(ulong messageId, RequestOptions options = null)
@@ -200,11 +200,11 @@ namespace Discord.Rest
         async Task<IReadOnlyCollection<IMessage>> IMessageChannel.GetPinnedMessagesAsync(RequestOptions options)
             => await GetPinnedMessagesAsync(options).ConfigureAwait(false);
         /// <inheritdoc />
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
-            => await SendFileAsync(filePath, text, isTTS, embed, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
+            => await SendFileAsync(filePath, text, isTTS, embed, options, isSpoiler).ConfigureAwait(false);
         /// <inheritdoc />
-        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.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options, isSpoiler).ConfigureAwait(false);
         /// <inheritdoc />
         async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
diff --git a/src/Discord.Net.Rest/Entities/Channels/RestGroupChannel.cs b/src/Discord.Net.Rest/Entities/Channels/RestGroupChannel.cs
index 39991d411..5cfe03f15 100644
--- a/src/Discord.Net.Rest/Entities/Channels/RestGroupChannel.cs
+++ b/src/Discord.Net.Rest/Entities/Channels/RestGroupChannel.cs
@@ -123,12 +123,12 @@ namespace Discord.Rest
         /// <exception cref="NotSupportedException"><paramref name="filePath" /> is in an invalid format.</exception>
         /// <exception cref="IOException">An I/O error occurred while opening the file.</exception>
         /// <exception cref="ArgumentOutOfRangeException">Message content is too long, length must be less or equal to <see cref="DiscordConfig.MaxMessageSize"/>.</exception>
-        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);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options, isSpoiler);
         /// <inheritdoc />
         /// <exception cref="ArgumentOutOfRangeException">Message content is too long, length must be less or equal to <see cref="DiscordConfig.MaxMessageSize"/>.</exception>
-        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<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options, isSpoiler);
 
         /// <inheritdoc />
         public Task TriggerTypingAsync(RequestOptions options = null)
@@ -178,11 +178,11 @@ namespace Discord.Rest
         async Task<IReadOnlyCollection<IMessage>> IMessageChannel.GetPinnedMessagesAsync(RequestOptions options)
             => await GetPinnedMessagesAsync(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);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
+            => await SendFileAsync(filePath, text, isTTS, embed, options, isSpoiler).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.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options, isSpoiler).ConfigureAwait(false);
         async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
 
diff --git a/src/Discord.Net.Rest/Entities/Channels/RestTextChannel.cs b/src/Discord.Net.Rest/Entities/Channels/RestTextChannel.cs
index 78bc7393f..dc86327bd 100644
--- a/src/Discord.Net.Rest/Entities/Channels/RestTextChannel.cs
+++ b/src/Discord.Net.Rest/Entities/Channels/RestTextChannel.cs
@@ -129,13 +129,13 @@ namespace Discord.Rest
         /// <exception cref="NotSupportedException"><paramref name="filePath" /> is in an invalid format.</exception>
         /// <exception cref="IOException">An I/O error occurred while opening the file.</exception>
         /// <exception cref="ArgumentOutOfRangeException">Message content is too long, length must be less or equal to <see cref="DiscordConfig.MaxMessageSize"/>.</exception>
-        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);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options, isSpoiler);
 
         /// <inheritdoc />
         /// <exception cref="ArgumentOutOfRangeException">Message content is too long, length must be less or equal to <see cref="DiscordConfig.MaxMessageSize"/>.</exception>
-        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<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options, isSpoiler);
 
         /// <inheritdoc />
         public Task DeleteMessageAsync(ulong messageId, RequestOptions options = null)
@@ -266,12 +266,12 @@ namespace Discord.Rest
             => await GetPinnedMessagesAsync(options).ConfigureAwait(false);
 
         /// <inheritdoc />
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
-            => await SendFileAsync(filePath, text, isTTS, embed, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
+            => await SendFileAsync(filePath, text, isTTS, embed, options, isSpoiler).ConfigureAwait(false);
 
         /// <inheritdoc />
-        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.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options, isSpoiler).ConfigureAwait(false);
         /// <inheritdoc />
         async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
diff --git a/src/Discord.Net.WebSocket/Entities/Channels/ISocketMessageChannel.cs b/src/Discord.Net.WebSocket/Entities/Channels/ISocketMessageChannel.cs
index 3c824166f..62f017138 100644
--- a/src/Discord.Net.WebSocket/Entities/Channels/ISocketMessageChannel.cs
+++ b/src/Discord.Net.WebSocket/Entities/Channels/ISocketMessageChannel.cs
@@ -38,7 +38,7 @@ namespace Discord.WebSocket
         ///     Sends a file to this message channel with an optional caption.
         /// </summary>
         /// <remarks>
-        ///     This method follows the same behavior as described in <see cref="IMessageChannel.SendFileAsync(string, string, bool, Embed, RequestOptions)"/>.
+        ///     This method follows the same behavior as described in <see cref="IMessageChannel.SendFileAsync(string, string, bool, Embed, RequestOptions, bool)"/>.
         ///     Please visit its documentation for more details on this method.
         /// </remarks>
         /// <param name="filePath">The file path of the file.</param>
@@ -46,11 +46,12 @@ namespace Discord.WebSocket
         /// <param name="isTTS">Whether the message should be read aloud by Discord or not.</param>
         /// <param name="embed">The <see cref="Discord.EmbedType.Rich" /> <see cref="Embed" /> to be sent.</param>
         /// <param name="options">The options to be used when sending the request.</param>
+        /// <param name="isSpoiler">Whether the message attachment should be hidden as a spoiler.</param>
         /// <returns>
         ///     A task that represents an asynchronous send operation for delivering the message. The task result
         ///     contains the sent message.
         /// </returns>
-        new Task<RestUserMessage> SendFileAsync(string filePath, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null);
+        new Task<RestUserMessage> SendFileAsync(string filePath, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false);
         /// <summary>
         ///     Sends a file to this message channel with an optional caption.
         /// </summary>
@@ -64,11 +65,12 @@ namespace Discord.WebSocket
         /// <param name="isTTS">Whether the message should be read aloud by Discord or not.</param>
         /// <param name="embed">The <see cref="Discord.EmbedType.Rich"/> <see cref="Embed"/> to be sent.</param>
         /// <param name="options">The options to be used when sending the request.</param>
+        /// <param name="isSpoiler">Whether the message attachment should be hidden as a spoiler.</param>
         /// <returns>
         ///     A task that represents an asynchronous send operation for delivering the message. The task result
         ///     contains the sent message.
         /// </returns>
-        new Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null);
+        new Task<RestUserMessage> SendFileAsync(Stream stream, string filename, string text = null, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false);
 
         /// <summary>
         ///     Gets a cached message from this channel.
diff --git a/src/Discord.Net.WebSocket/Entities/Channels/SocketDMChannel.cs b/src/Discord.Net.WebSocket/Entities/Channels/SocketDMChannel.cs
index cd03505ef..838fb8ef2 100644
--- a/src/Discord.Net.WebSocket/Entities/Channels/SocketDMChannel.cs
+++ b/src/Discord.Net.WebSocket/Entities/Channels/SocketDMChannel.cs
@@ -139,12 +139,12 @@ namespace Discord.WebSocket
             => ChannelHelper.SendMessageAsync(this, Discord, text, isTTS, embed, options);
 
         /// <inheritdoc />
-        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);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options, isSpoiler);
         /// <inheritdoc />
         /// <exception cref="ArgumentOutOfRangeException">Message content is too long, length must be less or equal to <see cref="DiscordConfig.MaxMessageSize"/>.</exception>
-        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<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options, isSpoiler);
         /// <inheritdoc />
         public Task DeleteMessageAsync(ulong messageId, RequestOptions options = null)
             => ChannelHelper.DeleteMessageAsync(this, messageId, Discord, options);
@@ -229,11 +229,11 @@ namespace Discord.WebSocket
         async Task<IReadOnlyCollection<IMessage>> IMessageChannel.GetPinnedMessagesAsync(RequestOptions options)
             => await GetPinnedMessagesAsync(options).ConfigureAwait(false);
         /// <inheritdoc />
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
-            => await SendFileAsync(filePath, text, isTTS, embed, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
+            => await SendFileAsync(filePath, text, isTTS, embed, options, isSpoiler).ConfigureAwait(false);
         /// <inheritdoc />
-        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.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options, isSpoiler).ConfigureAwait(false);
         /// <inheritdoc />
         async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
diff --git a/src/Discord.Net.WebSocket/Entities/Channels/SocketGroupChannel.cs b/src/Discord.Net.WebSocket/Entities/Channels/SocketGroupChannel.cs
index 07b7066b9..26fcbe83c 100644
--- a/src/Discord.Net.WebSocket/Entities/Channels/SocketGroupChannel.cs
+++ b/src/Discord.Net.WebSocket/Entities/Channels/SocketGroupChannel.cs
@@ -167,11 +167,11 @@ namespace Discord.WebSocket
             => ChannelHelper.SendMessageAsync(this, Discord, text, isTTS, embed, options);
 
         /// <inheritdoc />
-        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);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options, isSpoiler);
         /// <inheritdoc />
-        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<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options, isSpoiler);
 
         /// <inheritdoc />
         public Task DeleteMessageAsync(ulong messageId, RequestOptions options = null)
@@ -293,11 +293,11 @@ namespace Discord.WebSocket
             => await GetPinnedMessagesAsync(options).ConfigureAwait(false);
 
         /// <inheritdoc />
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
-            => await SendFileAsync(filePath, text, isTTS, embed, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
+            => await SendFileAsync(filePath, text, isTTS, embed, options, isSpoiler).ConfigureAwait(false);
         /// <inheritdoc />
-        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.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options, isSpoiler).ConfigureAwait(false);
         /// <inheritdoc />
         async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
diff --git a/src/Discord.Net.WebSocket/Entities/Channels/SocketTextChannel.cs b/src/Discord.Net.WebSocket/Entities/Channels/SocketTextChannel.cs
index 239d39eab..ca7ca11dc 100644
--- a/src/Discord.Net.WebSocket/Entities/Channels/SocketTextChannel.cs
+++ b/src/Discord.Net.WebSocket/Entities/Channels/SocketTextChannel.cs
@@ -165,13 +165,13 @@ namespace Discord.WebSocket
             => ChannelHelper.SendMessageAsync(this, Discord, text, isTTS, embed, options);
 
         /// <inheritdoc />
-        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);
+        public Task<RestUserMessage> SendFileAsync(string filePath, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false)
+            => ChannelHelper.SendFileAsync(this, Discord, filePath, text, isTTS, embed, options, isSpoiler);
 
         /// <inheritdoc />
         /// <exception cref="ArgumentOutOfRangeException">Message content is too long, length must be less or equal to <see cref="DiscordConfig.MaxMessageSize"/>.</exception>
-        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<RestUserMessage> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false, Embed embed = null, RequestOptions options = null, bool isSpoiler = false)
+            => ChannelHelper.SendFileAsync(this, Discord, stream, filename, text, isTTS, embed, options, isSpoiler);
 
         /// <inheritdoc />
         public Task DeleteMessagesAsync(IEnumerable<IMessage> messages, RequestOptions options = null)
@@ -302,11 +302,11 @@ namespace Discord.WebSocket
             => await GetPinnedMessagesAsync(options).ConfigureAwait(false);
 
         /// <inheritdoc />
-        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options)
-            => await SendFileAsync(filePath, text, isTTS, embed, options).ConfigureAwait(false);
+        async Task<IUserMessage> IMessageChannel.SendFileAsync(string filePath, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
+            => await SendFileAsync(filePath, text, isTTS, embed, options, isSpoiler).ConfigureAwait(false);
         /// <inheritdoc />
-        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.SendFileAsync(Stream stream, string filename, string text, bool isTTS, Embed embed, RequestOptions options, bool isSpoiler)
+            => await SendFileAsync(stream, filename, text, isTTS, embed, options, isSpoiler).ConfigureAwait(false);
         /// <inheritdoc />
         async Task<IUserMessage> IMessageChannel.SendMessageAsync(string text, bool isTTS, Embed embed, RequestOptions options)
             => await SendMessageAsync(text, isTTS, embed, options).ConfigureAwait(false);
diff --git a/src/Discord.Net.Webhook/DiscordWebhookClient.cs b/src/Discord.Net.Webhook/DiscordWebhookClient.cs
index 1253de0a3..5dc3d51aa 100644
--- a/src/Discord.Net.Webhook/DiscordWebhookClient.cs
+++ b/src/Discord.Net.Webhook/DiscordWebhookClient.cs
@@ -93,13 +93,13 @@ namespace Discord.Webhook
         /// <summary> Sends a message to the channel for this webhook with an attachment. </summary>
         /// <returns> Returns the ID of the created message. </returns>
         public Task<ulong> SendFileAsync(string filePath, string text, bool isTTS = false,
-            IEnumerable<Embed> embeds = null, string username = null, string avatarUrl = null, RequestOptions options = null)
-            => WebhookClientHelper.SendFileAsync(this, filePath, text, isTTS, embeds, username, avatarUrl, options);
+            IEnumerable<Embed> embeds = null, string username = null, string avatarUrl = null, RequestOptions options = null, bool isSpoiler = false)
+            => WebhookClientHelper.SendFileAsync(this, filePath, text, isTTS, embeds, username, avatarUrl, options, isSpoiler);
         /// <summary> Sends a message to the channel for this webhook with an attachment. </summary>
         /// <returns> Returns the ID of the created message. </returns>
         public Task<ulong> SendFileAsync(Stream stream, string filename, string text, bool isTTS = false,
-            IEnumerable<Embed> embeds = null, string username = null, string avatarUrl = null, RequestOptions options = null)
-            => WebhookClientHelper.SendFileAsync(this, stream, filename, text, isTTS, embeds, username, avatarUrl, options);
+            IEnumerable<Embed> embeds = null, string username = null, string avatarUrl = null, RequestOptions options = null, bool isSpoiler = false)
+            => WebhookClientHelper.SendFileAsync(this, stream, filename, text, isTTS, embeds, username, avatarUrl, options, isSpoiler);
 
         /// <summary> Modifies the properties of this webhook. </summary>
         public Task ModifyWebhookAsync(Action<WebhookProperties> func, RequestOptions options = null)
diff --git a/src/Discord.Net.Webhook/WebhookClientHelper.cs b/src/Discord.Net.Webhook/WebhookClientHelper.cs
index a02cb3e2f..311d58bda 100644
--- a/src/Discord.Net.Webhook/WebhookClientHelper.cs
+++ b/src/Discord.Net.Webhook/WebhookClientHelper.cs
@@ -35,16 +35,16 @@ namespace Discord.Webhook
             return model.Id;
         }
         public static async Task<ulong> SendFileAsync(DiscordWebhookClient client, string filePath, string text, bool isTTS, 
-            IEnumerable<Embed> embeds, string username, string avatarUrl, RequestOptions options)
+            IEnumerable<Embed> embeds, string username, string avatarUrl, RequestOptions options, bool isSpoiler)
         {
             string filename = Path.GetFileName(filePath);
             using (var file = File.OpenRead(filePath))
-                return await SendFileAsync(client, file, filename, text, isTTS, embeds, username, avatarUrl, options).ConfigureAwait(false);
+                return await SendFileAsync(client, file, filename, text, isTTS, embeds, username, avatarUrl, options, isSpoiler).ConfigureAwait(false);
         }
         public static async Task<ulong> SendFileAsync(DiscordWebhookClient client, Stream stream, string filename, string text, bool isTTS,
-            IEnumerable<Embed> embeds, string username, string avatarUrl, RequestOptions options)
+            IEnumerable<Embed> embeds, string username, string avatarUrl, RequestOptions options, bool isSpoiler)
         {
-            var args = new UploadWebhookFileParams(stream) { Filename = filename, Content = text, IsTTS = isTTS };
+            var args = new UploadWebhookFileParams(stream) { Filename = filename, Content = text, IsTTS = isTTS, IsSpoiler = isSpoiler };
             if (username != null)
                 args.Username = username;
             if (avatarUrl != null)