diff --git a/src/frontend/src/modals/IOModal/components/chatView/chatInput/chat-input.tsx b/src/frontend/src/modals/IOModal/components/chatView/chatInput/chat-input.tsx
index 9c4f25b8b..e2796cc93 100644
--- a/src/frontend/src/modals/IOModal/components/chatView/chatInput/chat-input.tsx
+++ b/src/frontend/src/modals/IOModal/components/chatView/chatInput/chat-input.tsx
@@ -1,4 +1,5 @@
 import { usePostUploadFile } from "@/controllers/API/queries/files/use-post-upload-file";
+import { ENABLE_IMAGE_ON_PLAYGROUND } from "@/customization/feature-flags";
 import useFileSizeValidator from "@/shared/hooks/use-file-size-validator";
 import useAlertStore from "@/stores/alertStore";
 import useFlowStore from "@/stores/flowStore";
@@ -64,7 +65,7 @@ export default function ChatInput({
   const handleFileChange = async (
     event: React.ChangeEvent<HTMLInputElement> | ClipboardEvent,
   ) => {
-    if (playgroundPage) {
+    if (playgroundPage && !ENABLE_IMAGE_ON_PLAYGROUND) {
       return;
     }
 
diff --git a/src/frontend/src/modals/IOModal/components/chatView/chatInput/components/input-wrapper.tsx b/src/frontend/src/modals/IOModal/components/chatView/chatInput/components/input-wrapper.tsx
index 4f2d517da..947f7f522 100644
--- a/src/frontend/src/modals/IOModal/components/chatView/chatInput/components/input-wrapper.tsx
+++ b/src/frontend/src/modals/IOModal/components/chatView/chatInput/components/input-wrapper.tsx
@@ -84,7 +84,8 @@ const InputWrapper: React.FC<InputWrapperProps> = ({
         </div>
         <div className="flex w-full items-end justify-between">
           <div className={isBuilding ? "cursor-not-allowed" : ""}>
-            {!playgroundPage && ENABLE_IMAGE_ON_PLAYGROUND && (
+            {(!playgroundPage ||
+              (playgroundPage && ENABLE_IMAGE_ON_PLAYGROUND)) && (
               <UploadFileButton
                 isBuilding={isBuilding}
                 fileInputRef={fileInputRef}
diff --git a/src/frontend/src/modals/IOModal/components/chatView/chatInput/hooks/use-drag-and-drop.ts b/src/frontend/src/modals/IOModal/components/chatView/chatInput/hooks/use-drag-and-drop.ts
index b8c137ef1..9e8192e6d 100644
--- a/src/frontend/src/modals/IOModal/components/chatView/chatInput/hooks/use-drag-and-drop.ts
+++ b/src/frontend/src/modals/IOModal/components/chatView/chatInput/hooks/use-drag-and-drop.ts
@@ -1,8 +1,11 @@
 import { ENABLE_IMAGE_ON_PLAYGROUND } from "@/customization/feature-flags";
 
-const useDragAndDrop = (setIsDragging: (value: boolean) => void) => {
+const useDragAndDrop = (
+  setIsDragging: (value: boolean) => void,
+  playgroundPage: boolean,
+) => {
   const dragOver = (e) => {
-    if (!ENABLE_IMAGE_ON_PLAYGROUND) return;
+    if (!ENABLE_IMAGE_ON_PLAYGROUND && playgroundPage) return;
     e.preventDefault();
     if (e.dataTransfer.types.some((type) => type === "Files")) {
       setIsDragging(true);
@@ -10,7 +13,7 @@ const useDragAndDrop = (setIsDragging: (value: boolean) => void) => {
   };
 
   const dragEnter = (e) => {
-    if (!ENABLE_IMAGE_ON_PLAYGROUND) return;
+    if (!ENABLE_IMAGE_ON_PLAYGROUND && playgroundPage) return;
     if (e.dataTransfer.types.some((type) => type === "Files")) {
       setIsDragging(true);
     }
@@ -18,6 +21,7 @@ const useDragAndDrop = (setIsDragging: (value: boolean) => void) => {
   };
 
   const dragLeave = (e) => {
+    if (!ENABLE_IMAGE_ON_PLAYGROUND && playgroundPage) return;
     e.preventDefault();
     setIsDragging(false);
   };
diff --git a/src/frontend/src/modals/IOModal/components/chatView/components/chat-view.tsx b/src/frontend/src/modals/IOModal/components/chatView/components/chat-view.tsx
index 5a22b6b62..23050e140 100644
--- a/src/frontend/src/modals/IOModal/components/chatView/components/chat-view.tsx
+++ b/src/frontend/src/modals/IOModal/components/chatView/components/chat-view.tsx
@@ -148,10 +148,13 @@ export default function ChatView({
   const { files, setFiles, handleFiles } = useFileHandler(currentFlowId);
   const [isDragging, setIsDragging] = useState(false);
 
-  const { dragOver, dragEnter, dragLeave } = useDragAndDrop(setIsDragging);
+  const { dragOver, dragEnter, dragLeave } = useDragAndDrop(
+    setIsDragging,
+    !!playgroundPage,
+  );
 
   const onDrop = (e) => {
-    if (!ENABLE_IMAGE_ON_PLAYGROUND) {
+    if (!ENABLE_IMAGE_ON_PLAYGROUND && playgroundPage) {
       e.stopPropagation();
       return;
     }