diff --git a/src/components/common/messaging/MessageBox.tsx b/src/components/common/messaging/MessageBox.tsx
index 66a87bca..17b3eb2d 100644
--- a/src/components/common/messaging/MessageBox.tsx
+++ b/src/components/common/messaging/MessageBox.tsx
@@ -477,8 +477,21 @@ export default observer(({ channel }: Props) => {
                             return send();
                         }
 
-                        if (e.key === "Escape" && replies.length > 0) {
-                            setReplies(replies.slice(0, -1));
+                        if (e.key === "Escape") {
+                            if (replies.length > 0) {
+                                setReplies(replies.slice(0, -1));
+                            } else if (
+                                uploadState.type === "attached" &&
+                                uploadState.files.length > 0
+                            ) {
+                                setUploadState({
+                                    type:
+                                        uploadState.files.length > 1
+                                            ? "attached"
+                                            : "none",
+                                    files: uploadState.files.slice(0, -1),
+                                });
+                            }
                         }
 
                         debouncedStopTyping(true);