Of course you should patch your Windows Server installations in a timely manner, however you choose to do it. I'm trying to upgrade a Server Core box to Windows Server 2016 but the setup dialog turns blank at one point and I can't continue. The solution is to restart the setup (not continuing from the last upgrade attempt) but when calling add the "/compat ignorewarning" switch, e.g.Admittedly, many of the Server Core benefits have become moot points with Windows Server 2016: The newly added security measures in Windows Server add a lot.
To allow even greater agility, but also to get the installation ‘just right’ using the Graphical User Interface (GUI), Microsoft offered to add and remove GUI layers in Windows Server 2012 and Windows Server 2012 R2.
Windows Server Update Services are the tools of choice of many administrators, since they allow for greater control and centralized reporting of updates in a networking environment.
In the latest incarnation of WSUS (as bundled with Windows Server 2012), the services are also capable of updating third-party software (like Oracle’s Java and Adobe’s Reader), can be managed through Power Shell, and (you’ve guessed it!
Also, many of the (graphical) tools we needed in Windows Servers to configure the Windows Server installation also have grown up and now offer command-line, if not Power Shell support.
Keeping a networking environment up to date can be a tricky task.
Microsoft is doing a pretty good job of giving you appropriate tools to keep software from Redmond up to date.