Hi all,
I had the same issue. My wife's calendar, which she shares with me, suddenly stopped syncing to my machines and devices. In fact, on one device, it would show some appointments and on others nothing. I, too, have spoken with all Apple Support levels, and I have uploaded the diagnostic files to Apple's engineers. I am expecting a callback tomorrow (Sunday) morning. However, I could not let it rest as it was bothering me. So, I think I have finally found a solution—at least one that is working now.
I will not go through all the troubleshooting steps; instead, this is the way; as of this writing, I fixed the issue. First, let me explain the hardware and setup. It is important to note that icloud.com always showed the correct information; the devices and machines weren't syncing.
Wife's System
—iMac M1
—iPhone 13 Pro
—iPad Pro (latest gen)
My Setup
—MacBook Pro M1 Max
—iMac Pro (Intel, of course)
—iPhone 13 Pro Max
—iPad Pro (latest gen)
First, I backed up my wife's shared calendar. Changed the name—disabled iCloud Sync on her machine. I generated a local calendar. I imported the local calendar into a new iCloud calendar.
I then disabled the calendar sync on all my machines and devices. I did a hard reset of my iPhone and iPad and rebooted both machines.
I then reshared her new iCloud calendar with me and accepted the invitation through iCloud.com. Shared calendars repopulated on iCloud.com just fine. On my MacBook Pro M1 MAX, I then enabled iCloud Sync again. It took a couple of minutes, but poof. All items now showed from her new shared calendar. I let it sit for a while and created tests back and forth; everything was fine.
I then enabled calendar sync on my iPhone 13 Pro Max, and poof, everything synced. I again tested creating and deleting events from both sides on her machine and my MacBook and iPhone.
Her iPhone and iPad never had an issue; it was only on my end since she shared the calendar with me. Now, I want to leave it like this for the time being to make sure nothing goes wonky again, but at least it's working on my laptop and iPhone.
It seems I've isolated it to either my iPad or iMac Pro. I have the feeling it is with my iPad, so I will later today enable calendar sync on the iMac Pro. If all goes well for a while, I most likely will format the iPad and start from scratch on the iPad as the last thing I want to do is go through this process again.
Please note: All devices and computers are and were completely up-to-date when the issue occurred, and it seemed to have happened when I updated everything.
I hope this helps, and I will keep you posted.