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IIS Web Gardens
Sometimes IIS servers have the Web Gardens feature enabled, and that can cause problems for CrissCross (or other ASP.NET web apps).
If you are getting lots of 'Failed to retrieve repdef object' and 'ASP.NET Session has expired' errors in the error log, it might be due to 'Web Gardens' being turned on on the IIS server. Usually 'Web Gardens' is off but some SSRS servers seem to have it on for some reason.
Basically 'Web Gardens' are when multiple worker processes get assigned to a single IIS Application Pool. This causes trouble for ASP.NET Sessions and caching (unless care has been taken to code round it). See here for background: http://nicholas.piasecki.name/blog/2009/02/on-web-gardens-aspnet-and-iis-60/
The way to fix it is by making sure that CrissCross was running in its own Application Pool, and then modifying the Application Pool settings so that on the 'Maximum number of worker processes' is set to 1. (Thats in the Application Pool properties, on the Performance tab). If 'Maximum number of worker processes' is greater than 1 then you're running 'web gardens' and the default asp.net session stuff won't work (unless you switch to more fancy ASP.NET session settings, see blog post).