After searching around for months on and off I finally decided to post this up.
We have an ASP.NET MVC app that uses enterprise library to cache items. We also use a windows service that every so often updates those cached items. Problem is that when the windows service updates the cached items, the mvc website does not see the updated cached items until we reset IIS. We have thought about putting some code in the service to restart the IIS service but think there has got to be a better way. There seems to be one other post that talks about removing items from an external app, but it doesn't go far enough.
We think it has something to do with the in memory version that is local to each instance of the cache manager but simply cannot find a way to bring it all together.