Depending on the business user working with Windchill (maybe a part time user), the Description associated with a context Role provides additional insight into what is expected of the individual in that role and/or what abilities the user assigned to the role is granted. As a result, the Role Description is something that is saved to the context Template.
Upon instantiating the context template, although the Roles are deployed, the Description for the role (as defined in the Template) does not instantiate.
The current workaround is to manually update/populate the Role Description for EVERY context created in Windchill.
This was reported to PTC, where a SPR was issued (# 532818) with a solution of "no plans to correct"