Copying login keychains between Macs fails on Secure Enclave Macs with Tahoe

Disturbing if true, as it suggests my "everything" backups aren't really full backups at all.

I wonder, if you have enabled iCloud keychain, does that provide another way to get your passwords back?

Suppose my MacBook is stolen, but I still have my iPhone. Could I use the passwords app on the iPhone to retrieve my passwords. Would that include all of them or only a subset?

This is pretty much how it's suppose to work...

Switching from macOS to Linux was quite painful because the security was so seamless on Mac. But I also realized I had no idea how my passwords are stored and under what guarantees. Learning and getting the hardware tokens to do it properly on Linux was a PITA. But reading this post made me feel a pinch better.

Does the macoOS login keychain get backed up by Time Machine backups in a way that could restore the keychain if the original machine's Secure Enclave is lost or destroyed?

It sounds like they are using envelope encryption and using the Secure Enclave to derive the row keys each time. Not really any easy way around that except they should provide a tool to export it, TBH. I am guessing they weren’t using envelope encryption before or they were deriving the row keys from the password. This is a secure design but more security usually means less usability these days.

It's always a good idea to plan to hang on to your old machine for a few weeks to ensure everything works properly on the new one. Apple makes that much easier to forget.

This was introduced, unannounced, in macOS 26.4! See my blog post for more information: https://lapcatsoftware.com/articles/2026/9/4.html

And yet if you click export it will gladly print out a plaintext csv with your whole life in passwords. Doesn't even attempt to zip it with password or something.

This is good.