diff --git a/src/rest/request_manager.ts b/src/rest/request_manager.ts
index 4eacb42bf..63c481964 100644
--- a/src/rest/request_manager.ts
+++ b/src/rest/request_manager.ts
@@ -1,5 +1,10 @@
 import { authorization, eventHandlers } from "../bot.ts";
-import { Errors, HttpResponseCode, RequestMethods } from "../types/mod.ts";
+import {
+  Errors,
+  FileContent,
+  HttpResponseCode,
+  RequestMethods,
+} from "../types/mod.ts";
 import {
   API_VERSION,
   BASE_URL,
@@ -155,8 +160,16 @@ function createRequestBody(body: any, method: RequestMethods) {
   }
 
   if (body?.file) {
+    if (!Array.isArray(body.file)) body.file = [body.file];
+
     const form = new FormData();
-    form.append("file", body.file.blob, body.file.name);
+    // form.append("file", body.file.blob, body.file.name);
+
+    body.file.map((file: FileContent, index: number) =>
+      // The key of the form data item must be unique; otherwise, Discordeno only considers the first item in the form data with the same names.
+      form.append(`file${index + 1}`, file.blob, file.name)
+    );
+
     form.append("payload_json", JSON.stringify({ ...body, file: undefined }));
     body.file = form;
   } else if (
diff --git a/src/types/channel.ts b/src/types/channel.ts
index fa1f03785..fbf6c41fa 100644
--- a/src/types/channel.ts
+++ b/src/types/channel.ts
@@ -111,7 +111,7 @@ export interface MessageContent {
   /** Whether this is a TextToSpeech message */
   tts?: boolean;
   /** The contents of the file being sent */
-  file?: { blob: unknown; name: string };
+  file?: FileContent | FileContent[];
   /** Embed object */
   embed?: Embed;
   /** JSON encoded body of any additional request fields. */
@@ -120,6 +120,11 @@ export interface MessageContent {
   replyMessageID?: string;
 }
 
+export interface FileContent {
+  blob: Blob;
+  name: string;
+}
+
 export interface AllowedMentions {
   /** An array of allowed mention types to parse from the content. */
   parse: ("roles" | "users" | "everyone")[];