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My most painful data loss was when I tried a Windows "alternative" called "Lindows" [0]. Touted as "Linux, but easy like Windows!."

So I put the disk in, and it says something like "Do you want to install Lindows?" with no options, no warnings or anything. So I hit Yes/Okay/whatever the single button on the screen was, and without zero warning, it proceeded to wipe my entire hard drive.

It's been 17 years and it still hurts :)

[0] https://en.wikipedia.org/wiki/Linspire



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