General Time Machine question relating to MacOS updates

I have run into the same issue. Open TM and then use the keys shift-command-c. This will bring upfront your main drive. You can now scroll back in time. Once you get where you want you can then open the drive and scroll down to your user library and then documents, downloads, etc. and find the item you want. Then copy to desktop and use or move from there.

Hey Adam Nitti,

It sounds like you're looking to restore data from your backup after updating. We can understand wanting to look into that further. We want to help.

You should be able to restore files from your backup using the steps here: Restore items backed up with Time Machine on Mac

If that's not working, let us know what happens when you try. Are you getting an error message? If so, what does that message say?

Thanks!

Adam Nitti wrote:

It's a long story, but I had to update my MacBook Pro (previously running Sierra) to Catalina recently and now I cannot access any of the files backed up to Time Machine prior to the OS Catalina update. Sorry if a dumb question, but is that not something you can access from prior OS installs, even if just wanting to restore individual documents/files from older backups? If that is not an option, how in the world do I access those files again? Thanks for any insight!

There have been issues here... not easily discernible.

How to access Time Machine files from previous OS install?

reference: https://discussions.apple.com/thread/5579823

If your new Mac inherits your backup history - Apple Support

https://support.apple.com/guide/mac-help/if-your-new-mac-inherits-your-backup-history-mh35732/mac

If you get a replacement (new) Mac, you probably want the Inherit or Reuse option.

If you get an additional Mac, you probably want the Create New Backup option.

thus the old adage— 3-2-1 Backup Strategy: three copies of your data, two different methods, and one offsite.

That key combo of keys someone else noted in an old chat discussion. See above link from leroydouglas.