Just as an fyi to anyone who has similar issues. WinCache v1.1.x would not write sessions to files under certain conditions. This means that all sessions are lost whenever an app-pool recycle occur. Here is the work around:
If your app-pool name has periods (.) in it, change them to underscores (_). So an app-pool named www.somesite.com should be renamed to www_somesite_com.
You can see the discussion here: