Yoku's Island Express

To start this quest, you need to lose a set amount of fruit from falling onto thorns during the pinball sections of the game. After set amounts of fruit lost, you'll get brief cutscenes that may seem odd. After losing enough fruit, eventually the cutscene will show shadow characters breaking free and running away. At this point, the quest can now be started and completed. Note that you will need the crimson ball color to be able to progress this quest. This is obtained by unlocking "Life finds a way" and then returning to Dipperloaf after five or so minutes have passed and the egg has hatched, rewarding you with the crimson ball color. You'll then need to head to the sprinkle dispensers in the middle of the map and color your ball crimson.

With all that done, you're now ready to do this quest. From the sprinkle dispensers where you color your ball crimson, head right into the little cave hole to drop down lower. Head left into the next cave hole to go even lower. Go down into the well on your immediate left. Now jump into the water on your left and swim under the land you jumped off of to find a guard in red. Talk to him to start the quest. You now need to head to the big piece of land shaped like a monkey holding up a platform above its head. If you pull up your map, it's near the lower middle and tough to miss. Go to the mushroom on its left side to launch into the monkey statue. Progress through the pinball sections inside to complete the area, then return to the red guard to complete the quest and unlock this achievement.