I did all the three endings and I think that achievement is ending-related, but I can't get it even doing the same ending twice

i dont understand how to get it

Was enjoying the hell out of this game, and then it crashed around 40 minutes in after Petal says something along the lines of "now i have to start living" after clicking on the bloody newspaper. Is this supposed to happen? is this something wrong with my system? when i reopened the game it sent me back to the beginning...