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and without proxy, Windows Update works just as it should! You are checking the configuration of older machines by opening up Internet Explorer and double-checking proxy settings…
Of course, you have some sort of proxy on your network, and you start troubleshooting this issue by testing on a proxy-free network… Still a bit confused, you have a great idea to check system proxy settings by running netsh winhttp show proxy – on older machines you’ll probably see something like this (which is probably OK, because you’ve just seen the Proxy Settings in IE, which are set to correct values): So, you’re (naturally) configuring new machines accordingly. Basically, you need to run netsh winhttp import proxy source=ie (after you’ve set the right proxy settings through IE dialog, of course) or set your system proxy by using the netsh winhttp set proxy proxy.mydomain.com:8080 command. So, remember – when using Windows Server 2016, set your system proxy settings by using the netsh command and everything will work just fine!
So, the next logical next step is to blame “those networking guys”, because updating your machine works fine, when not behind their “fancy proxy thing”. You will soon realize that you have some “old” Windows Server 2012 R2 (or even Windows 10) machines, which are updating just fine… and then you make sure that your new machines are having the same configuration – they have.
You can do further reading & testing, but the thing that helped in our case was setting the system (winhttp) proxy with netsh command, so that it actually imports IE proxy settings.
Incidentally, I tried to install Exchange 2016 on Server 2016 without a GUI but it appears not to be supported. Returning to the subject of updates, Brendan Power at Microsoft popped up on Reddit to say that this is a bug in in the settings: The "Available updates will be downloaded…" text in the UI is a bug that doesn’t represent the actual automatic update settings. That said, Windows Server 2016 is meant to follow the Long Term Servicing Branch (LTSB) model rather than the “Windows as a service” approach in Windows 10, unless you run Nano Server, according to this post.