Lost Secure Notes in Keychain

I’ve had multiple issues with my 2020 M1 MacAir, every time I upgraded OS, I was unable to update Apps, I’d have to erase and redownload fresh OS and restore from Time Machine. Support finally suggested I was bringing bad data over (over 15+ years I did a lot of terminal hacks), and I was able to erase and reload Ventura (13.5.2) and did not use Time Machine restore. Keychains and mail and just about everything else are iCloud synced, so that all came in fine. But I’ve lost Secure Notes in Keychain and all of my .sig files for mail. (.sig may not be correct term, it’s my signature files).
Apple Support just told me there is no way to pull my Secure Notes or my .sig files from Time Machine.
I’m devastated, I can’t stress how much important information is in my secure notes.
Any suggestions?

If nothing else works and if you have a complete backup of the info that you are missing; I’m pretty sure you could restore to another Mac, then at worst case copy and paste the info into a document that you could move to the mac that has the missing info and copy to the appropriate places. If you don’t have a spare mac you probably can get a used mac for a few hundred dollars.
If you try this, I would skip signing in with your apple id/icloud in the spare/temporary Mac so nothing tries to sync to the cloud.

What a terrific idea!! Thank you Steve!!

Something I do with my Keychain information is keep an encrypted backup on a USB memory stick that is kept in my “Go Bag”. In addition to emergency preparedness, doing this gives me a backup that is independent of Time Machine and Carbon Copy Cloner (the two backup methods I use).

Here are the steps I follow:

  1. In Finder, open a window that shows your Keychains folder (example path: Macintosh HD > Users > [your User name] > Library > Keychains)
  2. Create an encrypted Disk Image in Apple’s Disk Utility (File > New Image) that is big enough to hold everything in the Keychains folder.
  3. Drag copy Keychains to the Disk Image.
  4. Insert USB stick.
  5. Drag copy the Disk Image to the USB stick.

For maximum security, you could format the USB stick to be encrypted as well.

The Secure Notes are in a .keychain file — probably login.keychain, in ~/Library/Keychains (unless you chose a different keychain for those notes).

Find that file in your backup. Copy and rename it somewhere. The default location is ~/Library/Keychains, but you can put it anywhere.

In Keychain Access, choose File > Add Keychain… . Select your renamed keycahin file. It willl become available to Keychain Access in the “Custom Keychains” section. The password will be whatever you last used for that keychain.

(I tested this in Monterey; as far as I know, nothing has changed in Ventura.)