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Is there no key that syncs the achievements you've unlocked in the game itself? I don't want to lose all the progress I've made. When I first booted up Isaac with all DLC's installed it unlocked like 30 achievements for me, but not all of them like these two apparently.
If you've already beaten that boss years ago in the base game... try defeating it again? Maybe there's a save file flag that was added in later DLCs that you haven't obtained yet, so it's worth a shot.
That sounds like a good idea! I'll try it out tomorrow and post what my results were.
I just beat the boss and I unlocked both of the challenges. Thanks for the help!