Working with Fiddler, I found that Live Support Operator is making a call to "hostip.info", ostensibly to determine the country and city for an IP address. This call is returning a 502 "unable to connect" error, which may be what is causing the operator program to blow up.  HostIP.info appears to be offline.  Live Support Operator doesn't seem to be able to properly handle that situation.

 

Specifically, it makes a call like: