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Did you make sure to leave 1 person on guard when this happened?

Yes. Especially on the latest occurrence mentioned, the one where I had my friend play just yesterday (so the memory is really fresh in my mind). 

She got really lucky and had a decent roll the day before it happened so she was able to get enough wood and food for all 7 Campers, had 2 medication already prepared, and had someone on guard. In addition to that, they were all healthy and fed. Then the day ended, and we saw an immediate game over/all campers died screen. 

I decided to try again just now (only minutes ago), to see if I'd get more lucky, but had the same thing happen again. I wasn't paying attention to the day, but it was after day 16, and we were past where we moved to the second floor.

There were 6 campers alive. I had been extremely lucky on rolls just before this point so I was very confident with my resources. I had someone on guard, over 20 wood (was trying to prepare for the upcoming 20 wood check), over 10 food, 3 medicine, and no one was even exhausted that night. Then the day ended, and I got another instant "All Campers Died" screen.

(+1)

I'll take a look into this. I had to hastily throw this game together for the minijam and had limited time so I'm sure there's some weird bug I didn't see. I'll update the game if I find anything strange.