Several of our PlayBook users experienced an “encrypted filesystem did not unlock properly” error when bridging between BlackBerry and PlayBook after upgrading to OS 2.x. When experiencing this error it is not possible to establish a Bridging session.
What exactly goes on is unknown to me but all of our users with this exact issue have had previous bridging sessions with the 1.x PlayBook and their BlackBerry prior to upgrading. So maybe it is old (cached) information that is causing this. Deleting the current Bridging setup on both PlayBook and BlackBerry and re-establishing pairing does not solve the problem.
You may be able to use some of the Bridging functionality by accessing http://127.0.0.1:187 from the PlayBook browser but the only way to restore normal functionality is to wipe and reload the OS on the PlayBook.