Not all items form Keychain Access are under the Passwords App

I've managed to reset the IRC password, however I have three critical notes with security question pairs for an airline and two financial institutions that I can no longer access.

I accidentally updated my main workstation from Sequoia to Golden Gate.

D’oh!

Unfortunately, the Passwords App does not allow me to see a number of things that are stored in the Keychain Access App

Right. Passwords is very much focused on… well… passwords [1] and only deals with the data protection keychain. Keychain Access is the way to work with items in the file-based keychain, including secure notes.

If you’re unfamiliar with these terms, they’re explained in TN3137 On Mac keychain APIs and implementations.

As to why you can’t unlock your login keychain, I don’t have a definitive answer to that. My best guess is that it’s related to the protected entropy file stuff described in the most recent update to TN3137. However, to determine exactly what happened would require a lot more digging.

Do you have a backup of this Mac before you upgraded? If so, you could try to recover your login keychain from that. I have instructions on how to do that, for a very different reason, in The Care and Feeding of Developer ID.

Share and Enjoy
—
Quinn “The Eskimo!” @ Developer Technical Support @ Apple
let myEmail = "eskimo" + "1" + "@" + "apple.com"

[1] Oh, and passkeys.

As someone who used multiple features of Keychain Access over the years, while it has a cleaner interface, I find Passwords underwhelming.

BTW, Keychain Access lets me get at items in the iCloud Keychain with my login password.

Unfortunately, as the update was supposed to be from macOS 15.8 to 15.8.1, rather than 27.0.1, I didn't make a bootable backup.

Other than system files, my data lives on a separate NextCloud server (with off-site back-ups), so I normally don't worry too much when upgrading.

I didn't make a bootable backup.

You don’t need a bootable backup to recover keychains from macOS 15 [1]. Any backup of the files in ~/Library/Keychains should be sufficient.

Share and Enjoy
—
Quinn “The Eskimo!” @ Developer Technical Support @ Apple
let myEmail = "eskimo" + "1" + "@" + "apple.com"

[1] The same can’t be said of macOS 26, where the introduction of protected entropy files means that a simple backup of your home directory is not sufficient.

I ended up in this same situation, completely locked out of my keychain access after updating to golden gate and i have to restart. Loading a backed-up keychain fails and my login password isn't suitable (why would my login keychain not be my computer password is beyond me.)

i have a feeling it has to do with the entropy file. im not sure why this failed completely w/ golden gate and trying to work with an older one requires disabling SIP which is ... scary. At some point, I think i was running into a locked keychain on tahoe and changing my user password to the same password would make it work again.

I'm close to just loading tahoe up again or just giving up and restarting :/