Keychain Access Strange Behaviours (Beachballs, Password Manager Metadata entries, reminders to login to iCloud)

macOS 10.15.7 / Late 2013 iMac 27"

OK, this is a long one but I'll give all the info I can.

For a several weeks now, I've been experiencing issues with Keychain Access in Catalina. It takes ages to open, shows spinning beachballs and is glacial when entering a search string. I even get spinning beachballs when trying to close a window in Keychain Access app. Just now it took 20 seconds for the coloured buttons to become active after clicking a window in the app and a further five seconds of beachballing for the window to close.

Separately I've been getting repeated notifications to log into iCloud in system preferences to Update Apple ID settings.

This is utterly broken because it goes round in a circle, takes ages, asks for my Apple ID password (and computer password for my Monterey Mac) several times and ultimately achieves nothing. My password is correct - that isn't the problem. Sometimes it acts as though I've finally resolved it, but it always comes back. I tried logging out of iCloud and logging back in, to no avail.

After everything, the Apple ID overview pane still tells me "Some account services will not be available until you sign in again"

I'm clearly not the only one experiencing this. The problem is that Apple seems to have broken compatibility with [and/or] Apple ID / Keychain Access / iCloud in some older operating systems, notably Catalina.

...but not all older OSs. My High Sierra Mac (don't ask) has no issues with Keychain Access.

One more oddity - both keychains are now showing entries called Password Manager Metadata: [some keychain entry name], each of which corresponds to a Keychain entry. There's a (closed) thread about that here. One of the conclusions was that it's linked to the Password Manager system preference in macOS 13, but the assumption there is that the metadata stems from a conflict between Notes in Password Manager and Comments in Keychain Access app.

I demur. In my case there is absolutely no corrspondence between Comments in Keychain Access and the nine Keychain items with corresponding Password Manager Metadata entries. I don't have Ventura, so it can't be coming from Notes in Password Manager, I have never edited these entries directly via iCloud, and I have never updated these passwords on my iPhone.

All this peculiar behaviour strikes me as linked nonetheless, and the common starting point seems to be when I responded to a prompt to update accept new iCloud terms.

It didn't cause an issue for my High Sierra Mac, nor did it casue an issue for my Monterey Mac, but it's clearly created issues for my Catalina Mac. THe other possibility seems to be accepting end-to-end encryption as part of the iCloud terms update on my Monterey Mac, but it surprises me if this alone causes issues for a recent OS but not an older one (both 64 bit FWIW).

FWIW I'm conscious of the propter hoc fallacy, but the experience of others seems to corroborate my suspicions.

One solution that seems open is to reset the keychain, however the cost is "You will lose all items currently stored in these keychains" - and I fear the unresolved iCloud / Apple ID "some account services will not be available" issue is highly likely to casue a catch 22 situation leaving me worse off than I currently am.

Any suggestions?

Updating the OS on my Catalina machine is not an option, so please don't suggest that. Yes, it seems Apple has created a bug and can't be bothered to fix it becasue it only affects an out of support OS, albeit one that's just 5 years old and received its last update just 2.5 years ago. And that's completely, cynically unacceptable. But it doesn't help, and frnkly, we're used to it.

So, bright Ideas?

For me, it's moving to a different password manager altogether, but my favoured on, Sticky Password, doesn't seem to import iCloud keychain, just the login one. Keychain Access doesn't even have an export function afaik.

Maybe there's a terminal command?

Eeep.