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The achievement involves having Min, Maria and Lyssa (which is impossible in a normal playthrough, as you can only select two among these), as well as Stacy active.
Instead, navigate to Main Menu --> Bonus Content --> Endings and click on E15 - Waterfall (you'll need to complete it at least once, for it to be unlocked). Select all optional characters here and let the ending play out.
As soon as the scene with Lyssa, Gemma, Stacy and the MC ends, the achievement should unlock.
@CentAurora - you might wanna add this in 'The Tricky Achievements' guide.
So in the classroom scene on Day 16, I chose Freedom Now to release the cage. There may be other ways to remove it before meeting Jessie but I don't know so that's what I did. Then when meeting Jessie on Day 16 I selected "I'm open to it" to have fun with her. This triggered the meeting with Jessie at the end of Day 17, and I chose the options from this guide to get the achievement.