We've been using the 2.2x series SS with great success on IIS /w Isapi Rewrite (v3x). Looking towards the future of SS and all the modular upgrades in the works we are looking to upgrade to the 2.3x series SS.
Considering the exact same release (12/18/2008 trunk) works perfectly fine on Apache/Linux, there must be a problem with either the ISAPI_REWRITE or IIS.
Has anyone had success in fixing or at least determining the problem at hand? I'm about to go back to tackling it now.