I currently have a Shoretel Server running Server 2003 x32 as a virtual machine paired with a ShoreGear 90 switch and another unused switch of the same model being reserved for manual failover. I am getting the software mailed to me from my partner, but with limited support since the server is in a relatively remote area. I am tempted to upgrade the OS at the same time as performing the upgrade, but want to know if there are any horror stories or advice I should know about before diving in.

I'm upgrading from Shoretel 9.2 Build. I will be upgrading first to version 10.1 then finally to 11.1. The system has been bullet proof since it was installed and we are upgrading mainly to get a client that is a little more modern.

My question boils down to: Should I even bother with an OS upgrade or even possibly a fresh install of Windows with an install of Shoretel 11.1 and just transfer the configuration?

Should I just stay with Server 2003 since it is supported in my target version of Shoretel and the upgrade will be more than enough to keep me busy as a novice?