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Maybe it is a good time to issue a ticket with Esri Tech Support. You could also publish on the http://forums.arcgis.com/forums/5-ArcGIS-Desktop-General and http://forums.arcgis.com/forums/7-ArcGIS-Desktop-Installation-Configuration where you can get more people looking at your problem.
I will have to agree with Alexey, please log a tech support incident. They are best prepared to handle these situations.
Thank you both. I've gone ahead and filled out an incident report. I will post the results here.
It appears as though it has something to do with me getting switched to a roaming profile. Still not sure how to fix it, but I've figured out that if I log in via my local profile, all is well again.