1) If you get an Exception saying "Session state has created a session ID, but cannot save it because the response was already flushed by the application" then make sure you have set DisplayWhenNewSession to 'false'
http://www.codeproject.com/useritems/WebRequestPanel.asp
you lose session state when the application pool is recycled (unless you r using sql server to store your sessions, of course) if that is your problem, and it occurs frequently, then someone missconfigured your webserver as app. pool recycling can be regulated in IIS. i personally think that the error message received sounds like its the app_pool... just a guess, but i'd take a look at the iis settings... try putting the app in a seperate pool for testing, or regulate the recyle settings.
reference
http://www.eggheadcafe.com/community/aspnet/6/10008376/re.aspx