The earliest date at which you can obtain an achievement will be in parentheses (Day X) at the end of the description. Day and night 0 are before Alex sleeps in the inn for the first time.

All achievements can be acquired in a single playthrough.

#1 - Word Finder



Complete the word search on a newspaper outside of Alex's bedroom. (Night 0)

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#2 - Coffee Guzzler



Drink 16 cups of coffee and get a game over screen. The coffee can be found in Concilio's detective agency - the starting location. Note that the coffee at the inn does not work. (Day 0 only)

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#3 - Gravity



When fixing the bike, make sure that there is less pressure than necessary - you can press done immediately without pumping air into the tire at all. (Day 1)

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#4 - Feasting



Eat 6 items off the menu. (Night 0)

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#5 - Didn't Learn



Touch the boards in the boathouse and get a game over screen, once at day and once at night time. (Day 1 - Night 1)

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#6 - Unscrambler



Finish 100 levels of the unscrambling game in Alex's bedroom. If you get stuck, you can use this online unscrambler: https://wordunscrambler.me/ (Night 0)

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#7 - Blowing Up



When fixing the bike tire, keep pumping air into it until you die. (Day 1)

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#8 - Quick Aim



Finish all 20 levels of Geese vs. Fox. (Day 2)

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#9 - Perfect Score



Finish all 20 levels of Geese vs. Fox without losing any health. (Day 2)

1# - Mr. Quackers



Squeeze the rubber duck 20 times. It can be found in a drawer in the dining room of the inn. (Night 0)

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2# - Sleepyhead



Try to sleep at daytime 15 times. (Day 1)

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3# - Cycling is Life



Use the bike 30 times.

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4# - Culprit Catcher (Spoilers)



Once you've broken out of the bunker after Lauren traps you in there, head for the exit to the tunnels and immediately pull down the lever to trap her. This will promptly drop the achievement. (Night 3, at the end of the game)

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5# - Easter Egg



Credits to tishinna32 for this one!
On the third floor of the inn (the one with Shirley's room on it), there is an armchair with a white pillow. Click on it (there is no cursor indication of it being clickable) to find a phone charm behind the pillow. (Day 1)