This video guide contains all achievements / trophies in A Way Out in chronological order. Nothing is missable, you can redo anything via chapter select and unless written otherwise, both players earn the achievement / trophy at the same time (They can only be earned with a full copy of the game, not the free friend pass). This game can only be played with 2 players, there is no Singleplayer mode.
#1 The Dip - 0:25
Chapter: Escape - The Yard
Leo must do 20 Dips in a row on the prison yard.
#2 Freedom - 1:29
Chapter: Escape - Prison Escape
Free the Caged Parrot in the Warden's Office.
#3 Take a Breather - 2:49
Chapter: Fugitives - Breather
At the start of the chapter walk to the right. There's a rock both players need to sit on to enjoy the view.
#4 In Sync - 3:49
Chapter: Fugitives - The Farmstead
Go into the house of the old couple. Vincent must play the piano and Leo the Banjo. Each player must hit 20 notes in a row without missing a single one. If one player messes up you have to get another 20 correct notes.
#5 Timeless Treasure - 5:11
Chapter: Fugitives - The Farmstead
Go into the house of the old couple. On the ground floor is a clock, both players need to interact with it at the same time. This opens a secret door upstairs, go into that hidden room to pick up a sword from the chest.
#6 Take it for a Spin - 6:03
Chapter: Fugitives - The Farmstead
Climb the windmill and interact with it a few times to spin it up.
#7 No Cheating - 7:03
Chapter: Preperation - Reunion
Talk to the woman with the baseball bat in the starting area of the chapter. Then go to the trailer to her right side to find her husband. Then talk to her again to get the trophy. #8 You Started It - 8:19
Chapter: Preperation - Reunion
Both players need to sit on the swing set at the same time.
#9 Home Run - 9:16
Chapter: Preperation - Reunion
At start of chapter, head to the right. There's a guy with a baseball bat. Talk to him and then try to hit a Home Run. Swing the bat as soon as the pitcher starts the throw-animation. You must hit the ball in a straight line over the fence really far away. Only unlocks for the player getting the home run, the 2nd player has to do it again.
#10 Backseat Mechanic - 9:58
Chapter: Preperation - Reunion
Vincent must bring a Wrench to the woman repairing a bike. Then help her start the bike. Leo should stay inside the trailer until the trophy pops and not progress any further (unlocks for both players).
#11 Managed Anger - 11:23
Chapter: Preperation - Violent Questioning
Talk to the guy on the chair and choose to push back the chair. Leo must then pick the purse from the table, drop it on the floor, and lean over the table. Vincent must then use an object to torture the guy which triggers a dream sequence.
#12 Live the Dream - 12:58
Chapter: Preperation - A Nie Life
After riding the elevator both players must sit on the couch in front of the TV. Watch TV until Leo falls asleep.
#13 Break from Reality - 14:16
Chapter: Vengeance - Lift Off
Both players need to play the arcade at start of chapter.
#14 Mayday! - 14:38
Vengeance - Lift Off
Leo has to interact with the Helicopter at start of chapter.