When I am in the training module, I attempt to update an existing dashboard and add it to the roles I am testing. I have found that the changes I made adding shortcuts do not apply, therefore I created a new dashboard and apply the changes to the roles I am testing and that works just fine. All I am doing is adding shortcuts to the Home Tab. There is a warning that tabs cannot be changed on existing published dashboards. I wonder if this is part of the issue.

Next there appears to be duplicate roles in the system, those with a bundle installed and those that do not have a bundle associated with them. I've heard bundles are sketchy and you don't want to add too many... is this one of the reasons why?