We noticed a while back that the CU updates for Server 2016 were constantly failing so i took a look at event viewer and found:
Next i headed off to the UpdatesHandler logon the server and noted:
Spot the 10 minutes in between the flag being set and the cancel…
So I did a bit of research and happened across this: https://blogs.msdn.microsoft.com/minfangl/2012/08/17/configuration-manager-may-fail-to-install-exchange-rollup-kb2706990-kb2734323-because-of-timeout/ – sounded like my issue so I checked and the Max Run Time on the update was set to 10 minutes. Set this to 600, cleared the cache and ran the cycles then tried the update again.
Note: this will only work for that CU – when it is released the next month you will need to do the process again so stay tuned for my colleagues blog on a script to implement to fix this ongoing!
Hope it helps!