Game:

The Uncertain: Light At The End (2020)

Duration: 0:00

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Game: https://store.steampowered.com/app/925570/The_Uncertain_Light_At_The_End/

Requires at least 3 playthroughs for all the achievements.
Both the "good" ending achievements can be unlocked in the same playthrough, but the two "bad" ending achievements require separate playthroughs.
The two "bad" ending achievements require separate playthroughs because of the very first choice in the pharmacy. Otherwise the two playthroughs are identical.

0:00 Start
8:52 Choice #1 (Help Park)
27:09 Fail QTE (Database Puzzle)
39:41 Fail QTE (Lose Brian)
56:35 Antisocial Club -- Maintain negative relations with all group members by the end of the game.