Can't update High Sierra through a proxy

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Level 1

9 points

Can't update High Sierra through a proxy

Greetings,

I'm experience a problem with systems that either shipped with High Sierra or were updated to High Sierra. I've tested with 10.13.0 and 10.13.1 with the latest security patches applied and the symptoms are the same.

The computer is aware of the proxy via auto-discovery, and is able to proxy other content, but is no longer able to access OS updates through the App Store-- the tab is typically grayed out.

I have opened literally every single apple.com or Apple-related host requested by the computer I'm using for testing, and nothing is working.

Putting the computer outside the proxy for updating is not an option. I'm running Squid 3.1.23 and not caching. Is there any necessary traffic that now requires something other than TCP/80 or TCP/443? This configuration works fine for Sierra and earlier.

Anything else I should try? For what it's worth, I don't really want to break it to upper management that we'll have to stop buying Macs... but putting systems outside the proxy is really and truly not an option for anything other than testing.

MacBook Pro TouchBar and Touch ID, macOS High Sierra (10.13.1)

Posted on Dec 1, 2017 2:21 PM

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Answer 1

Dec 4, 2017 2:20 PM in response to roneill12

I'm experiencing the same basically. I've an iMac at work and our network has HTTP proxies between it and the Internet. Instead of the "Auto Proxy Discovery" though, we have "Automatic Proxy Configuration" with a "Proxy Configuration File" URL.

The end result is the same though; Updates through the App Store fail to connect to Apple's servers through the Proxy - for some reason it's not picking up the Proxy settings. Everything else is working fine with these settings.

I've found a workaround though; manually setting the "Secure Web Proxy (HTTPS)" value with the specific host and port (and, if necessary, credentials) of the proxy server will allow the Updates to work. The downside here is that all of the crazy complicated stuff that's typically handled automatically (changing server names, proxy bypass settings, etc) must be handled manually. I have a pretty long-and-growing list of Bypass domains...

Hope that helps you, and anyone else who finds this. I tripped over it pretty early in High Sierra (10.13.0) and it's persisted so far through 10.13.1.

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Answer 2

roneill12 Author

Level 1

9 points

Dec 4, 2017 2:22 PM in response to Michael Ferry

Thanks for the response, Michael.

Unfortunately manually setting the HTTPS proxy still gives me the same results, and the update tab remains grayed out.

It looks like I may need to build a special proxy configuration just for High Sierra and test. I don't have full time access to the system under test so apologies if responses are slow.

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Answer 3

Dec 4, 2017 2:29 PM in response to roneill12

I'm a little iffy on if you also have to set "HTTP Proxy" too. My test this afternoon worked without it, but it started downloading an update while it was enabled. Go figure. I haven't had to set any of the others, and of course left the "Automatic" with the URL enabled as well.

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Answer 4

Dec 6, 2017 7:19 AM in response to roneill12

Update/Correction - You do indeed have to set both "Web Proxy (HTTP)" AND "Secure Web Proxy (HTTPS)" for Software Update to function properly. Oops on my part from my original testing.

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