In the midst of all the Windows 10 upgrading the Size Matters crew thought it would be a good idea to do an episode on when to upgrade your servers and desktops at your SMB. We talk about tools and caveats that we've personally run into while running these upgrades. As with most things, a lot of it comes down to the people that actually have to use the operating systems. It's a good idea to make sure folks are comfortable with the new OS. Of course you immediately think of end users moving to Windows 8.1 or Windows 10 and the kind of problems that might occur. But there were also some big changes from Server 2008 to Server 2012. You definitely don't want to make your admins lives harder when they're trying to troubleshoot other problems. Listen to the full podcast to hear some of our tips, tricks, and regrets.