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For keep's chamber spam 'pose' on the mirror until it stops mirroring you, then talk. As for Violet, it appears she is unable to move to level 9 right now.

Anyone else having trouble accessing Annie's expedition? Also, all my achievements seem to be messed up. Is there a way to fix this or is this an unsolvable problem?

I love how the game doesn't try to force a romantic outcome like most other visual novels do. It's  just a story of a sad and alone friend trying to not be sad and alone anymore, very heartbreaking in a way