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A recent Mac update deleted or lost all of my AI files, I looked in the recovery directory, qand there are twenty some files there, but Illustrator is not prompting to recover them, how do I recover the files in recovery? I can't use File>Open because the "Library" location is not available, even when holding down the option key. I was also surprised that none of my files were in the cloud, I guess I have to specify "save as cloud document"? Any tips would be appreciated.
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Before updating your operating system, alsways make a backup.
It might also be a good idea to keep the system and your work files on different volumes.
And then also make a lot of backups along the way, so you have different versions of your files.
But if you can't find your files by name, then they are pretty certainly gone.
You haven't saved them in Creative Cloud, Google Drive, iCloud or the like?