What version of Windchill are you currently running? 11.1 M020-CPS20
Describe the problem you are trying to solve. Please include detailed documentation such as screenshots, images or video.
Desktop Integration keeps a cache of the status for a Windchill document, so if it was the latest version and not checked out it will show like this allowing the document to be checked out and back in even after multiple users have made changes to the version without notifying the user if DTI.