Well, yeah, there was a time for that.
But, I can guess I can openly say this twenty years later, I was helping out one of the admins of the one of the largest warez sites in Central Europe and when that was raided (Operation Fastlink) -- police only found the proxies and couldn't find the owner so no one ever got indicted over this site -- I had a little chat with myself and, as I said above, closed that chapter of my life.
That server was really something else: imagine a normal mid tower chassis PC of the era but stuffed with IDE cards and next to it several piles of hard drives separated by little pieces of wood so they didn't overheat from touching. By the end, if memory serves, it was multiple terabytes.
It's extremely tedious for a human, and the pay-off is relatively low, as hinted by the parent (what recent DRMed games are even any good?). I do wonder whether anyone has tried setting a well trained AI on the problem though.
That was exactly my thought, if it is just brute force understanding debugging/assembly code a LLM could help.
I'm not an expert on it but my understand is that one part is basically have a VM with custom opcodes, and every opcode is randomized and the set of opcodes used is a subset of a larger pool. Then the code running in the VM is autogenerated from normal code using these confusing and randomly selected made up opcodes. And that is only 1 piece.