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Pirating games you own?
(infosec.pub)
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I think the only game I have tried that with that worked has been Oblivion and Shivering Isles. Some of them are so old, they don't have any keys. Like Quake and Doom. But those were put in bundles and with updated engine ports and such a couple years ago on Steam and I got those. Like the entire pre-2016 Doom collection, plus some other games on the original engine for $5 total. Not a bad deal. Some of those games I didn't actually already own, too, like Strife and Hexen 2. Always wanted Strife, but only had the shareware as a kid. Couldn't beat that as a kid back then anyway; I only ever got through the entire thing pirating it in my 20's at a time when it wasn't able to be purchased anywhere.
Now that you mention the older games you own. It might be worth it to make some backups in the form of iso's or copies. In case they get disk rot at some point. I think some of them must be close to 30 years old now.
Funny you mention Strife. I never really knew about Strife until much later when I found out about it. I have played the shareware version of Heretic quite a lot. But what really fascinated me back then where the early Grand Theft Auto and Carmageddon games. I guess my interest for cars translated into my games as well. Since those are technically open world driving games beside other things.