diff --git a/src/components/middle/composer/AttachmentModal.tsx b/src/components/middle/composer/AttachmentModal.tsx
index 2f09c8c2e..9c8b71459 100644
--- a/src/components/middle/composer/AttachmentModal.tsx
+++ b/src/components/middle/composer/AttachmentModal.tsx
@@ -264,7 +264,7 @@ const AttachmentModal: FC<OwnProps & StateProps> = ({
         : isSilent ? onSendSilent : onSend;
       send(isSendingCompressed, shouldSendGrouped);
       updateAttachmentSettings({
-        shouldCompress: isSendingCompressed,
+        shouldCompress: shouldSuggestCompression === undefined ? isSendingCompressed : undefined,
         shouldSendGrouped,
       });
     }
diff --git a/src/components/middle/composer/hooks/useAttachmentModal.ts b/src/components/middle/composer/hooks/useAttachmentModal.ts
index cefb0ed2f..0e491c7f7 100644
--- a/src/components/middle/composer/hooks/useAttachmentModal.ts
+++ b/src/components/middle/composer/hooks/useAttachmentModal.ts
@@ -79,6 +79,7 @@ export default function useAttachmentModal({
 
         setShouldForceAsFile(Boolean(shouldForce && canSendDocuments));
         setShouldForceCompression(!canSendDocuments);
+        setShouldSuggestCompression(undefined);
       }
     },
   );