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iCloud Drive does not allow you to recover files if you put them into the trash and empty it by accident. I learned this the hardest of ways.

That seems... reasonable? You have to trash the files and empty the trash before you lose them. Isn't that what the trash is for?

Issue is I accidentally used cmd+delete which deletes items immediately. And I’m so used to how Dropbox does it that it wasn’t my assumption.

Accidentally lost a bunch of data that way, figured I’d spread the word.