How can someone know if you had specific files on a drive?

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I already know about hard drives keeping the file after deletion until something else rewrites it, I’d like to know if someone could find out about your personal things by analizing files you saved along with those things or something like that.

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Sure, if they have ongoing access to your hard drive, they can read all of it. There are special evil-doer tools which make this easier, but they are going to be expending work to learn all about you. It might turn out that you’re not worth it, depending on who you are.

But, if you’re worth billions, they might expend a lot of work to steal all your money.

Yes; here is how:

1. recover your hard drive.
2. recover your browser settings, including cookies. (your browser also keeps passwords this way if you tell it to store password)
3. use the recovered session data (or stored passwords) to authenticate to an online store like Amazon
4. examine your order history from store.
5. also possible to scope out connected devices in your house by examining mac addresses, though this is hit or miss because mac’s aren’t persisted on disk typically (but could be in swap or other areas)
6. if the above fails, you can always recover the wifi password and connect to it that way.