Mike,
Unfortunately we don't test CCS debugger in Virtual Machines, nor our emulator third parties, therefore anything can happen under these conditions. Some of our attempts to use emulators in VMs are described in the page below, but I am trying to check if the XDS2xx family can work.
http://processors.wiki.ti.com/index.php/VMware_with_CCS
I will report back here and update the page accordingly, ok?
I apologize for the inconvenience,
Rafael