GPOs probably set correct, firewalls disabled for test purposes. I get this in the event viewer on the 2008 R2 machine (our administrative console server): There was a problem interacting with COM object 833E4010-AFF7-4AC3-AAC2-9F24C1457BCE. An outdated version might be installed, or the component might not be installed at all. This seems to indicate that Remote Assistance from 2008 R2 is trying to use Help & Support (the guid) instead of MSRA. Bug or am I missing something?