Liz:
In OE, go to File | Workstation Options and select the tab labelled "Specifications". If the Pick Slip isn't already pointing to PrintBoss, make the change. Note that "Workstation" is meant literally; you will need to make the change on each computer running OE.

A new version of OE will not need a newer version of PrintBoss. The next time would likely be when you change to a new operating system (ie. from XP to Windows 7 or Windows 8).