diff --git a/src/structures/Webhook.js b/src/structures/Webhook.js
index 4d96382ac..240ea1fd8 100644
--- a/src/structures/Webhook.js
+++ b/src/structures/Webhook.js
@@ -105,14 +105,22 @@ class Webhook {
       options = {};
     }
     if (options.file) {
-      if (typeof options.file === 'string') options.file = { attachment: options.file };
-      if (!options.file.name) {
-        if (typeof options.file.attachment === 'string') {
-          options.file.name = path.basename(options.file.attachment);
-        } else if (options.file.attachment && options.file.attachment.path) {
-          options.file.name = path.basename(options.file.attachment.path);
-        } else {
-          options.file.name = 'file.jpg';
+      if (options.files) options.files.push(options.file);
+      else options.files = [options.file];
+    }
+
+    if (options.files) {
+      for (let i = 0; i < options.files.length; i++) {
+        let file = options.files[i];
+        if (typeof file === 'string') file = { attachment: file };
+        if (!file.name) {
+          if (typeof file.attachment === 'string') {
+            file.name = path.basename(file.attachment);
+          } else if (file.attachment && file.attachment.path) {
+            file.name = path.basename(file.attachment.path);
+          } else {
+            file.name = 'file.jpg';
+          }
         }
       }
       return this.client.resolver.resolveBuffer(options.file.attachment).then(file =>
diff --git a/src/structures/interfaces/TextBasedChannel.js b/src/structures/interfaces/TextBasedChannel.js
index f7fde7319..8fb7995ec 100644
--- a/src/structures/interfaces/TextBasedChannel.js
+++ b/src/structures/interfaces/TextBasedChannel.js
@@ -88,7 +88,7 @@ class TextBasedChannel {
     }
 
     if (options.files) {
-      for (const i in options.files) {
+      for (let i = 0; i < options.files.length; i++) {
         let file = options.files[i];
         if (typeof file === 'string') file = { attachment: file };
         if (!file.name) {