Currently for Insync version 4.9.389 there is a bug where the "Prompt for User on Upload" feature is not assigning dictations to the user selected. This is a problem when multiple physicians use the same Olympus 5000 voice recorder. More information on setting up this feature can be found here: How To Set Up InSync When You Have One Recorder For Multiple Physicians
If the Olympus 5000 is not assigned to any user, then the Clinician will be blank in InCommand and InScribe. If the recorder has been setup for a user, then the dictations will always upload with that clinician's name despite what is inputted on the prompt for user.
This has been repaired in the newest version of InSync which can be installed by following this link: http://www.emdat.com/software/insync.asp