Chester will first spawn after the Eye Bone is placed in the player's inventory. He will then follow the Eye Bone from that point on. As long as the Eye Bone is in the player's possession, Chester will follow the player. If the Eye Bone is dropped on the ground or stored somewhere (even inside Chester himself), he will stop following the player and remain with the Eye Bone.
Chester regenerates Health at a rate of 22.5 HP every 3 seconds. When killed, he drops all of the items stored inside, and the Eye Bone will close its eye. If he dies while burning, any flammable items that he was carrying will be set on fire and burn to Ashes. Chester will respawn in one game day, wherever the Eye Bone happens to be.
Shadow Chester is a special version of Chester. Chester will only transform into Shadow Chester on a Full Moon and with at least one Nightmare Fuel in each of his 9 inventory slots. When those two conditions are met, he will consume the Nightmare Fuel and transform into Shadow Chester. (If Chester does not transform, drop the Eye bone then pick it up again.) Shadow Chester's perk is an additional three (3) inventory slots (for a total of twelve slots). If he dies, he will respawn as normal Chester. The Eye Bone's fur changes color from light brown to dark brown while Chester is transformed.
Snow Chester is a special version of Chester. Chester will only transform into Snow Chester on a Full Moon and with at least one Blue Gem in each of his 9 inventory slots. When those two conditions are met, he will consume the Blue Gems and transform into Snow Chester. Snow Chester's perk is the added ability to act as a mobile Ice Box, as he will preserve perishable items for twice as long (halves spoilage). Like normal Chester, he provides 9 inventory slots (which can also be used to store non-Food items). If he dies, he will respawn as normal Chester. The Eye Bone's fur changes color from light brown to white while Chester is transformed.
- Stacks of Mosquitoes and Killer Bees inside Chester allow him to be turned into a walking bomb that will unleash pain upon death. It's a good idea to drop the Eye Bone if the player plans on doing this; otherwise, they may end up too close to the carnage and suffer terrible consequences.
- Since Chester regenerates health at a fast rate, he can be a useful tool in restoring the player's health. If Chester is attacked with the Bat Bat, the player will regain health from the hit with no risk of being attacked but any followers will attack chester.
- It may be a good idea to keep the Eye Bone in a Backpack so that when armor is equipped, Chester will remain near the Backpack while enemies are dealt with.
- Krampus can steal the Eye Bone if it is in a Backpack. If Krampus despawns with the Eye Bone, it will be gone permanently (for that World only).
- Chester can only transform into Shadow Chester or Snow Chester if the required materials to do so are placed inside the normal version of Chester. In other words, it is impossible for Shadow Chester to transform into Snow Chester (and vice versa).
- The Eye Bone can be dropped on the ground (to free an inventory slot), when not using Chester, without worry of losing it. There is nothing in the game that can affect an Eye Bone lying on the ground (Mobs won't steal it, it's fire-proof, etc.).
- In the Reign of Giants DLC, the best way to deal with Overheating is with two Thermal Stones and Snow Chester. The player can put the two Stones in Snow Chester until they reach their coldest point. Then they can keep one in their inventory to keep them cool and when it gets too hot they can swap that stone with the cold one that is inside Snow Chester. By the time the second stone warms up, the previous one will have cooled in Snow Chester, leaving a cold Thermal Stone always available for the player.
- Chester was added in the Spoiled Rotten update.
- Chester's name is a pun on him being a mobile chest.
- Chester is one of the few Mobs that cannot be frozen.
- Krampus cannot steal from Chester. However, Chester can be killed, allowing Krampus to steal items that were stored in Chester.
- Chester cannot be healed using healing items.
- If Fireflies are stored inside of Chester, he will sometimes give off a tiny amount of light.
- Shadow Chester was implemented after achieving $25,000 in total pledges during .
- Snow Chester was implemented after achieving $120,000 in total pledges during Klei's Chester Plush Kickstarter.
- When killed, Chester will respawn when the eyebone opens its eye or left on the ground.
- According to Wilson, Chester is an esq, which is short for esquire. Esquire means attorney.
- Before the All's Well That Maxwell update, it was possible to obtain two Chesters when traveling between levels.
- Chester sometimes may not transform to Snow or Shadow variants. Dropping the Eye Bone and then picking it up again may fix the issue.
- In the Shipwrecked DLC, it is possible to bring Chester to the world by clicking on the dropped Eye Bone while teleporting via the Seaworthy. However, doing this will spawn an entirely new Chester, which means that objects stored inside him will not transfer. The old Chester will remain in the original world, safe with all things inside him.