diff --git a/src/Discord.Net.Rest/Entities/Channels/ChannelHelper.cs b/src/Discord.Net.Rest/Entities/Channels/ChannelHelper.cs
index c5d264ade..66f0b2539 100644
--- a/src/Discord.Net.Rest/Entities/Channels/ChannelHelper.cs
+++ b/src/Discord.Net.Rest/Entities/Channels/ChannelHelper.cs
@@ -338,6 +338,9 @@ namespace Discord.Rest
             string filePath, string text, bool isTTS, Embed embed, AllowedMentions allowedMentions, MessageReference messageReference, MessageComponent component, ISticker[] stickers, RequestOptions options, bool isSpoiler, Embed[] embeds)
         {
             string filename = Path.GetFileName(filePath);
+            if (filename == null || !filename.Contains('.'))
+                throw new ArgumentException("Make sure that the file path has a file name and a valid file extension.");
+
             using (var file = File.OpenRead(filePath))
                 return await SendFileAsync(channel, client, file, filename, text, isTTS, embed, allowedMentions, messageReference, component, stickers, options, isSpoiler, embeds).ConfigureAwait(false);
         }
@@ -346,6 +349,9 @@ namespace Discord.Rest
         public static async Task<RestUserMessage> SendFileAsync(IMessageChannel channel, BaseDiscordClient client,
             Stream stream, string filename, string text, bool isTTS, Embed embed, AllowedMentions allowedMentions, MessageReference messageReference, MessageComponent component, ISticker[] stickers, RequestOptions options, bool isSpoiler, Embed[] embeds)
         {
+            if (filename == null || !filename.Contains('.'))
+                throw new ArgumentException("Make sure that the file path has a file name and a valid file extension.");
+
             embeds ??= Array.Empty<Embed>();
             if (embed != null)
                 embeds = new[] { embed }.Concat(embeds).ToArray();
diff --git a/src/Discord.Net.WebSocket/Entities/Interaction/Message Components/SocketMessageComponent.cs b/src/Discord.Net.WebSocket/Entities/Interaction/Message Components/SocketMessageComponent.cs
index 051a290e6..2e48b6dd9 100644
--- a/src/Discord.Net.WebSocket/Entities/Interaction/Message Components/SocketMessageComponent.cs	
+++ b/src/Discord.Net.WebSocket/Entities/Interaction/Message Components/SocketMessageComponent.cs	
@@ -245,9 +245,9 @@ namespace Discord.WebSocket
 
         /// <inheritdoc/>
         public override async Task<RestFollowupMessage> FollowupWithFileAsync(
+            Stream fileStream,
+            string fileName,
             string text = null,
-            Stream fileStream = null,
-            string fileName = null,
             Embed[] embeds = null,
             bool isTTS = false,
             bool ephemeral = false,
@@ -287,8 +287,8 @@ namespace Discord.WebSocket
 
         /// <inheritdoc/>
         public override async Task<RestFollowupMessage> FollowupWithFileAsync(
+            string filePath,
             string text = null,
-            string filePath = null,
             string fileName = null,
             Embed[] embeds = null,
             bool isTTS = false,
diff --git a/src/Discord.Net.WebSocket/Entities/Interaction/Slash Commands/SocketAutocompleteInteraction.cs b/src/Discord.Net.WebSocket/Entities/Interaction/Slash Commands/SocketAutocompleteInteraction.cs
index 9164bfdd6..fb6aa2a76 100644
--- a/src/Discord.Net.WebSocket/Entities/Interaction/Slash Commands/SocketAutocompleteInteraction.cs	
+++ b/src/Discord.Net.WebSocket/Entities/Interaction/Slash Commands/SocketAutocompleteInteraction.cs	
@@ -34,7 +34,7 @@ namespace Discord.WebSocket
 
         internal new static SocketAutocompleteInteraction Create(DiscordSocketClient client, Model model, ISocketMessageChannel channel)
         {
-            var entity =  new SocketAutocompleteInteraction(client, model, channel);
+            var entity = new SocketAutocompleteInteraction(client, model, channel);
             entity.Update(model);
             return entity;
         }
@@ -84,11 +84,11 @@ namespace Discord.WebSocket
 
         /// <inheritdoc/>
         [Obsolete("Autocomplete interactions cannot have followups!", true)]
-        public override Task<RestFollowupMessage> FollowupWithFileAsync(string text = null, Stream fileStream = null, string fileName = null, Embed[] embeds = null, bool isTTS = false, bool ephemeral = false, AllowedMentions allowedMentions = null, RequestOptions options = null, MessageComponent component = null, Embed embed = null) => throw new NotSupportedException();
+        public override Task<RestFollowupMessage> FollowupWithFileAsync(Stream fileStream, string fileName, string text = null, Embed[] embeds = null, bool isTTS = false, bool ephemeral = false, AllowedMentions allowedMentions = null, RequestOptions options = null, MessageComponent component = null, Embed embed = null) => throw new NotSupportedException();
 
         /// <inheritdoc/>
         [Obsolete("Autocomplete interactions cannot have followups!", true)]
-        public override Task<RestFollowupMessage> FollowupWithFileAsync(string text = null, string filePath = null, string fileName = null, Embed[] embeds = null, bool isTTS = false, bool ephemeral = false, AllowedMentions allowedMentions = null, RequestOptions options = null, MessageComponent component = null, Embed embed = null) => throw new NotSupportedException();
+        public override Task<RestFollowupMessage> FollowupWithFileAsync(string filePath, string text = null, string fileName = null, Embed[] embeds = null, bool isTTS = false, bool ephemeral = false, AllowedMentions allowedMentions = null, RequestOptions options = null, MessageComponent component = null, Embed embed = null) => throw new NotSupportedException();
 
         /// <inheritdoc/>
         [Obsolete("Autocomplete interactions cannot have normal responses!", true)]
diff --git a/src/Discord.Net.WebSocket/Entities/Interaction/SocketBaseCommand/SocketCommandBase.cs b/src/Discord.Net.WebSocket/Entities/Interaction/SocketBaseCommand/SocketCommandBase.cs
index c2a7d5409..189a51e41 100644
--- a/src/Discord.Net.WebSocket/Entities/Interaction/SocketBaseCommand/SocketCommandBase.cs
+++ b/src/Discord.Net.WebSocket/Entities/Interaction/SocketBaseCommand/SocketCommandBase.cs
@@ -159,8 +159,8 @@ namespace Discord.WebSocket
 
         /// <inheritdoc/>
         public override async Task<RestFollowupMessage> FollowupWithFileAsync(
+            Stream fileStream,
             string text = null,
-            Stream fileStream = null,
             string fileName = null,
             Embed[] embeds = null,
             bool isTTS = false,
@@ -181,7 +181,7 @@ namespace Discord.WebSocket
             Preconditions.AtMost(allowedMentions?.UserIds?.Count ?? 0, 100, nameof(allowedMentions.UserIds), "A max of 100 user Ids are allowed.");
             Preconditions.AtMost(embeds?.Length ?? 0, 10, nameof(embeds), "A max of 10 embeds are allowed.");
             Preconditions.NotNull(fileStream, nameof(fileStream), "File Stream must have data");
-            Preconditions.NotNullOrWhitespace(fileName, nameof(fileName), "File Name must not be empty or null");
+            Preconditions.NotNullOrEmpty(fileName, nameof(fileName), "File Name must not be empty or null");
 
             var args = new API.Rest.CreateWebhookMessageParams
             {
@@ -201,8 +201,8 @@ namespace Discord.WebSocket
 
         /// <inheritdoc/>
         public override async Task<RestFollowupMessage> FollowupWithFileAsync(
+            string filePath,
             string text = null,
-            string filePath = null,
             string fileName = null,
             Embed[] embeds = null,
             bool isTTS = false,
@@ -222,7 +222,12 @@ namespace Discord.WebSocket
             Preconditions.AtMost(allowedMentions?.RoleIds?.Count ?? 0, 100, nameof(allowedMentions.RoleIds), "A max of 100 role Ids are allowed.");
             Preconditions.AtMost(allowedMentions?.UserIds?.Count ?? 0, 100, nameof(allowedMentions.UserIds), "A max of 100 user Ids are allowed.");
             Preconditions.AtMost(embeds?.Length ?? 0, 10, nameof(embeds), "A max of 10 embeds are allowed.");
-            Preconditions.NotNullOrWhitespace(filePath, nameof(filePath), "Path must exist");
+            Preconditions.NotNullOrEmpty(filePath, nameof(filePath), "Path must exist");
+
+            fileName ??= Path.GetFileName(filePath);
+
+            if (fileName == null || !fileName.Contains('.'))
+                throw new ArgumentException("Make sure that the file path has a file name and a valid file extension.");
 
             var args = new API.Rest.CreateWebhookMessageParams
             {
diff --git a/src/Discord.Net.WebSocket/Entities/Interaction/SocketInteraction.cs b/src/Discord.Net.WebSocket/Entities/Interaction/SocketInteraction.cs
index b4297b4bd..47b0ebcb6 100644
--- a/src/Discord.Net.WebSocket/Entities/Interaction/SocketInteraction.cs
+++ b/src/Discord.Net.WebSocket/Entities/Interaction/SocketInteraction.cs
@@ -157,7 +157,7 @@ namespace Discord.WebSocket
         /// <returns>
         ///     The sent message.
         /// </returns>
-        public abstract Task<RestFollowupMessage> FollowupWithFileAsync(string text = null, Stream fileStream = null, string fileName = null, Embed[] embeds = null, bool isTTS = false, bool ephemeral = false,
+        public abstract Task<RestFollowupMessage> FollowupWithFileAsync(Stream fileStream, string fileName, string text = null, Embed[] embeds = null, bool isTTS = false, bool ephemeral = false,
             AllowedMentions allowedMentions = null, RequestOptions options = null, MessageComponent component = null, Embed embed = null);
 
         /// <summary>
@@ -176,13 +176,13 @@ namespace Discord.WebSocket
         /// <returns>
         ///     The sent message.
         /// </returns>
-        public abstract Task<RestFollowupMessage> FollowupWithFileAsync(string text = null, string filePath = null, string fileName = null, Embed[] embeds = null, bool isTTS = false, bool ephemeral = false,
+        public abstract Task<RestFollowupMessage> FollowupWithFileAsync(string filePath, string text = null, string fileName = null, Embed[] embeds = null, bool isTTS = false, bool ephemeral = false,
             AllowedMentions allowedMentions = null, RequestOptions options = null, MessageComponent component = null, Embed embed = null);
 
         /// <summary>
         ///     Gets the original response for this interaction.
         /// </summary>
-        /// <param name="options">The request options for this async request.</param>
+        /// <param name="options">The request options for this <see langword="async"/> request.</param>
         /// <returns>A <see cref="RestInteractionMessage"/> that represents the initial response.</returns>
         public Task<RestInteractionMessage> GetOriginalResponseAsync(RequestOptions options = null)
             => InteractionHelper.GetOriginalResponseAsync(Discord, Channel, this, options);
@@ -191,7 +191,7 @@ namespace Discord.WebSocket
         ///     Edits original response for this interaction.
         /// </summary>
         /// <param name="func">A delegate containing the properties to modify the message with.</param>
-        /// <param name="options">The request options for this async request.</param>
+        /// <param name="options">The request options for this <see langword="async"/> request.</param>
         /// <returns>A <see cref="RestInteractionMessage"/> that represents the initial response.</returns>
         public async Task<RestInteractionMessage> ModifyOriginalResponseAsync(Action<MessageProperties> func, RequestOptions options = null)
         {
@@ -203,7 +203,7 @@ namespace Discord.WebSocket
         ///     Acknowledges this interaction.
         /// </summary>
         /// <param name="ephemeral"><see langword="true"/> to send this message ephemerally, otherwise <see langword="false"/>.</param>
-        /// <param name="options">The request options for this async request.</param>
+        /// <param name="options">The request options for this <see langword="async"/> request.</param>
         /// <returns>
         ///     A task that represents the asynchronous operation of acknowledging the interaction.
         /// </returns>