One of the things I have noticed since starting to deploy Windows Server 2016 is that the cumulative updates can fail to install when deployed from SCCM. It starts to run but then times out due to the maximum run time having been reached. By default this is set to 10 minutes. However due to the updates being larger and taking longer to install than updates prior to the cumulative updates era 10 minutes doesn’t seem to be long enough. The fix for this is to simply increase the maximum run time for cumulative updates for both Windows Server 2016 and Windows 10 from 10 minutes to 30 minutes.
This is a bit tedious as you’ll have to do it every month for both Windows Server 2016 and every version of Windows 10 you have in your environment. Hopefully Microsoft soon catches on to this and changes the default run time to 30 minutes so that this ceases to be an issue. There is already a Configuration Manager UserVoice entry for this idea, so if you’re reading this, pop over and vote to increase its visibility!