I took over an SBS 2011 server that hasn't been updated in over a year. I am migrating them to Windows 2019 and need to do updates before migration. What is the best way to update the server? Should I do Windows Update or just download the latest from Microsoft or some other method?
Just run Windows Update from the Control Panel. If you find that no updates are available but you know the server is behind on updates check the typical SBS WSUS policies, see screenshot.