When you upload a file to media library, right after it’s uploaded it doesn’t get selected automatically. The selection persists in whichever file or folder you had selected previous to the upload. You have to manually select it after the upload. Several clients of mine have told that they made mistakes with that as the behaviour is not that intuitive. They usually upload and then use to hit the insert button right away (and they insert the wrong file). Is there a way to configure / fix that?