What plugin were you using for the chat transcripts? Monitoring plugin? Or are you referring to Message Audit Policy option? Audit Policy is saving logs in Openfire\logs dir, so you can just move that dir to a new server (or just move whole Openfire dir). With Monitoring plugin i suppose it is saving logs in a databse, so you should move your database too, If you are using the Embedded database, then you should move openfire\embedded-db dir to your new place. If you are just doing simple upgrade, then you shouldnt do anything. Well, you can make a backup before upgrading, of course.