Figured it out after some further prodding, I can get the clip to happen if I'm holding up-right to run into the bed while pressing A.
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Train's all good now, but, uh, I think I broke everything sleeping in Annie's room. I even talked to Nero and saved like the dummy I am...
(luckily I managed to bail myself out by just editing the save file to move my coordinates, but yeah whoops)
I keep getting softlocked on the train, after defeating Oakley I can't leave the room. There's a blinking arrow to say I should be able to go down, but I can't. Also can't even reset the room with the Dark Card, and after restarting the train section three times I still get the same result.
Linux build, in case it matters.