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Do you have the cheat flag active? It prevents achievements.

(+1)

Yeah I learned that the hard way with the Anal Virigin path. And I deleted all my saves for it cause I thought aye I musta already gotten em'. Might wanna consider having it deactivated as a default maybe.

Ah, I'm not sure, but it might be the case. I'll restart my save files and make sure it's turned off.

Nah fam, you turn it off in settings or options at the main menu. I believe X means it's on and a clear box means it's off.