macOS 12 Monterey issue with Safari when using authenticated proxy frustrating corporate network users, but probably not for long

macOS 12 Monterey is Apple’s latest operating system. Released on October 25 last year, the OS brings in several new features and support for Apple devices released after 2013, which is really impressive.

However, macOS 12 Monterey users have reported several issues such as Spotlight and Finder app crashing, slow internet speed, and frequent Wi-Fi disconnection.


Now, corporate users who updated their systems to macOS 12 Monterey are reporting that they are unable to load any pages in Safari when connected to an authenticated proxy.

Users say that other browsers like Chrome seem to be working just fine, indicating that the issue lies somewhere with Safari.

Moreover, it looks like Safari starts loading just fine whenever they clear the app cache or use some other browser to load a page and switch back.


After upgrading to Monterey version, we found a problem with Safari. When connecting to the corporate network via vpn (cisco any connect – version 4.10.03104), we cannot access external sites, links do not open in the browser and internal sites (bypassing the proxy) open. If you open the same link in another browser (Google Chrome / Edge / Firefox) – everything works. The problem only occurs in the Safari browser on Monterey, in Big Sur and earlier versions – everything works correctly. sniffed traffic with a network analyzer when Safari used – you can see, that when the proxy server asked for credentials for authorization – Safari does not send anything, we get an error code 407 “proxy authentication required” Does anyone have the same problem? Or is it already a solution?

I just upgraded my Mac book pro to Monterey and coincidentally JAMF was pushed to my machine from our IT group. We have Cisco VPN. And the problem is Chrome will open any web page, but safari will not open anything. I repeat, chrome works but safari does not. So, it’s not exactly as Joel_Rohland posted, but similar. Happens whether I’m logged into the VPN or not. Apple support had me re-install Monterey from the recovery screen. That did not fix the problem. The next apple tech had me create a new user, and the problem still is there.

While Apple is yet to yet to say anything on the matter, it looks like macOS Monterey 12.2 b2 has fixed the issue where Safari is unable to connect when using an authenticated proxy.

I’ve been testing 12.2 b2 and this issue seems to have been resolved for us. I would conduct testing with this beta of Monterey and confirm it also resolves the issue.

We hope Apple releases the fix in the coming days since the issue has been rampant since last year. Rest assured, when they do, we will let you know so stay tuned for updates.

Note: We have more such stories in our dedicated Apple Section so be sure to follow them as well.

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Anurag Chawake

My fascination with technology and computers goes back to the days of Windows XP. Since then, I have been tinkering with OS, mobile phones, and other things. When I am not working on anything, you will find me enjoying video games on some Discord server.