macOS 27.3 Beta 1 (26C5035r) FINALLY has functioning iCloud Private Relay in a virtual machine again, and seems to be much faster logging into an Apple ID in System Settings compared to 27.2. Hoping this doesn't get broken again over the course of the beta cycle.

I installed the public build of 27.2 26B123 and opened a 26.6.2 VM, had it go through the software update to 26.7.2 25G332, and seems to be functioning just fine now. Not sure whether 27.2 or 26.7.2 had the changes, but seems to be fixed if anyone else can test it on their machines as well.

Black screen on OS upgrade appears to be fixed in 27.2 and 26.6.2 iCloud Private Relay issue continues in macOS 27.2 26B123 public release. Not sure what else to do, it's been 6 weeks since my initial reports to Apple, and yet to have any of it be noticed.

Issue continues in macOS 27.2 RC. No response from Apple to submitted feedback.

iCloud Private Relay is still not functional in macOS 27.2 beta 4 VMs. No response from Apple to submitted feedback.

I updated the Host OS to macOS 27.2 beta 3 today to test, and that has also not resolved the hanging macOS 26.7 VM hang when upgrading issue. I posted a little bit about it as well, along with iCloud Private Relay not functioning within macOS 27 guests as of macOS 27.0 Developer Beta 6, and macOS 27.2 beta 3 has still not fixed that issue either. https://developer.apple.com/forums/thread/847322

That seems to be one of the same issues, but I am experiencing it on an M5 Max 16-inch MacBook Pro as well The other issue I have being that iCloud Private Relay stopped functioning in Golden Gate guest virtual machines starting with developer beta 6 of Golden Gate and has continued in every build since. Tahoe and earlier guests seem to remain functioning normally with iCloud Private Relay within virtual machines.

These issues still continue to plague the final releases of 26.7.1 and 27.0.1, and there hasn't been any communication to the feedback reports I submitted. It affects all third-party virtual machine software, but in particular the Parallels Desktop forums are filling up with confused customers unable to upgrade their 26.6.2 and earlier Tahoe machines to 26.7.1, leaving them vulnerable to the security issues those updates are supposed to fix. There is still no available IPSW provided by Apple beyond macOS 26.6.2 that users could use for a clean install in a new virtual machine as a workaround.

iCloud Private Relay continues not to function in today's release of macOS 27.2 Beta 2 within virtual machines. The black screen issue continues to affect macOS Tahoe virtual machines, as today's 26.7.1 RC2 continues to have the black screen upon update reboot.