This issue requires a few manual steps that you need to do on your Mac to update Keychain Access settings.
Follow these steps:
- In Sketch, navigate to Plugins > Gallery > Sign out of Gallery.
- Click Yes to confirm.
- On your Mac, search for and launch the app Keychain Access.
- In the left Keychains menu open the login list.
- In the list of login items, you should see an entry called authorization. To confirm that it’s the right one, double click on it and then click on the Access Control tab. Sketch should appear beneath Always allow access by these applications.
- Right click on authorization and click on Delete.
- To confirm these steps resolved the issue, upload from Gallery twice. You should only be prompted to login the first time.
- If the above steps do not resolve the issue, file feedback.
