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At The Tale End isn't a game I know terribly much about, other than that it's pretty short, doesn't involve combat, and that it's set after the ending of Ye Old Generic JRPG.

Having done the ending sequence for this game multiple times, I still don't understand what the actual trigger for the loop stopping is. Putting my (very rusty) programmer's hat on, I'm guessing that what's supposed to happen is that the game checks whether or not you meet the requirements when you open up the chest and take the key. It could, however, be entirely possible that the game actually forces you to loop twice before letting you get the true ending.

I will say that I'm not a fan of the decision being made here — the earlier loop, where you got kicked back to the start of the sequence if you didn't drug your friends, was much better implemented, and felt way less random. It was honestly a pretty frustrating way to end the game.

You can find the translator's page here: https://vgperson.com/games/taleend.htm