iCloud Keychain Not Syncing

Hi all,

I've been having significant problems with iCloud Keychain approximately since my upgrade to iOS11/MacOS High Sierra.

The problem has to do with my iCloud keychain passwords, WiFi networks, and synched credit card numbers not updating between my devices. Everything on my Mac is correct, but the problem is on my iPhone. All the saved info on my passwords has not been updating in months. There's no new passwords from November or December, passwords that have changed on my Mac have not changed on my iPhone, and credit cards that have been added/removed aren't changed on my iPhone.

So far, I've deactivated iCloud keychain on both devices, deleted the saved passwords on my phone when prompted, kept the passwords on my Mac when prompted, then turned on iCloud keychain for my Mac to, in theory, upload the correct copy of all my passwords. But, if I go to activate again on my phone, it rarely actually updates. I've only been able to trigger my phone to download the keychain passwords by adding a device to my iCloud (in this case, my wife's MacBook Air), as strange as that sounds. That device receives the most correct passwords. But, even in that instance, passwords do download on my phone, but it's the same old passwords that I've been stuck with.

I'm out of options, phone support is stumped, and I'd really like this to work. I'm hoping someone has encountered something similar and might be able to help. The only thing that sticks out to me is, once I've deleted all the passwords on my phone, there is a username/password entry with a blank website entry that can't be deleted. I don't know if that's what's causing the problem, but it might be related.

Thanks so much!