diff --git a/pkg/interface/src/views/apps/chat/components/chat.tsx b/pkg/interface/src/views/apps/chat/components/chat.tsx
index 56fab6c72..18036660f 100644
--- a/pkg/interface/src/views/apps/chat/components/chat.tsx
+++ b/pkg/interface/src/views/apps/chat/components/chat.tsx
@@ -79,7 +79,7 @@ export class ChatScreen extends Component<ChatScreenProps, ChatScreenState> {
   }
 
   onDragEnter(event) {
-    if (!this.readyToUpload() || !event.dataTransfer.files.length) {
+    if (!this.readyToUpload() || (!event.dataTransfer.files.length && !event.dataTransfer.types.includes('Files'))) {
       return;
     }
     this.setState({ dragover: true });
@@ -149,7 +149,12 @@ export class ChatScreen extends Component<ChatScreenProps, ChatScreenState> {
             this.setState({ dragover: true });
           }
         }}
-        onDragLeave={() => this.setState({ dragover: false })}
+        onDragLeave={(event) => {
+          const over = document.elementFromPoint(event.clientX, event.clientY);
+          if (!over || !event.currentTarget.contains(over)) {
+            this.setState({ dragover: false });
+          }}
+        }
         onDrop={this.onDrop.bind(this)}
       >
         {this.state.dragover ? <SubmitDragger /> : null}
diff --git a/pkg/interface/src/views/apps/chat/components/lib/ChatInput.tsx b/pkg/interface/src/views/apps/chat/components/lib/ChatInput.tsx
index 200e02817..c0a1daa9f 100644
--- a/pkg/interface/src/views/apps/chat/components/lib/ChatInput.tsx
+++ b/pkg/interface/src/views/apps/chat/components/lib/ChatInput.tsx
@@ -160,10 +160,14 @@ export default class ChatInput extends Component<ChatInputProps, ChatInputState>
     if (!this.readyToUpload()) {
       return;
     }
+    if (!this.s3Uploader.current || !this.s3Uploader.current.inputRef.current) return;
     this.s3Uploader.current.inputRef.current.files = files;
-    const fire = document.createEvent("HTMLEvents");
-    fire.initEvent("change", true, true);
-    this.s3Uploader.current?.inputRef.current?.dispatchEvent(fire);
+    setTimeout(() => {
+      if (this.s3Uploader.current.state.isUploading) return;
+      const fire = document.createEvent("HTMLEvents");
+      fire.initEvent("change", true, true);
+      this.s3Uploader.current?.inputRef.current?.dispatchEvent(fire);
+    }, 200);
   }
 
   render() {