diff --git a/src/Discord.Net.Rest/Entities/Messages/MessageHelper.cs b/src/Discord.Net.Rest/Entities/Messages/MessageHelper.cs
index 384be196..a0aab863 100644
--- a/src/Discord.Net.Rest/Entities/Messages/MessageHelper.cs
+++ b/src/Discord.Net.Rest/Entities/Messages/MessageHelper.cs
@@ -99,7 +99,9 @@ namespace Discord.Rest
             }
             else
             {
-                var apiArgs = new UploadFileParams(args.Attachments.Value.ToArray())
+                var attachments = args.Attachments.Value?.ToArray() ?? Array.Empty<FileAttachment>();
+
+                var apiArgs = new UploadFileParams(attachments)
                 {
                     Content = args.Content,
                     Embeds = apiEmbeds?.ToArray() ?? Optional<API.Embed[]>.Unspecified,
diff --git a/src/Discord.Net.WebSocket/Entities/Interaction/MessageComponents/SocketMessageComponent.cs b/src/Discord.Net.WebSocket/Entities/Interaction/MessageComponents/SocketMessageComponent.cs
index 8758b987..6691bc6e 100644
--- a/src/Discord.Net.WebSocket/Entities/Interaction/MessageComponents/SocketMessageComponent.cs
+++ b/src/Discord.Net.WebSocket/Entities/Interaction/MessageComponents/SocketMessageComponent.cs
@@ -286,7 +286,9 @@ namespace Discord.WebSocket
             }
             else
             {
-                var response = new API.Rest.UploadInteractionFileParams(args.Attachments.Value.ToArray())
+                var attachments = args.Attachments.Value?.ToArray() ?? Array.Empty<FileAttachment>();
+
+                var response = new API.Rest.UploadInteractionFileParams(attachments)
                 {
                     Type = InteractionResponseType.UpdateMessage,
                     Content = args.Content,
diff --git a/src/Discord.Net.Webhook/WebhookClientHelper.cs b/src/Discord.Net.Webhook/WebhookClientHelper.cs
index 535d0fb8..373c6f42 100644
--- a/src/Discord.Net.Webhook/WebhookClientHelper.cs
+++ b/src/Discord.Net.Webhook/WebhookClientHelper.cs
@@ -109,7 +109,9 @@ namespace Discord.Webhook
             }
             else
             {
-                var apiArgs = new UploadWebhookFileParams(args.Attachments.Value.ToArray())
+                var attachments = args.Attachments.Value?.ToArray() ?? Array.Empty<FileAttachment>();
+
+                var apiArgs = new UploadWebhookFileParams(attachments)
                 {
                     Content = args.Content.IsSpecified ? args.Content.Value : Optional.Create<string>(),
                     Embeds =