Dungeon of Mandom VIII is a press-your-luck dungeon delve in which 2-4 players take turns essentially daring each other to go into a dungeon with less equipment than they start off with while filling the dungeon with monsters. Players can win the game by winning two rounds or get eliminated from the game by losing two rounds.

The game is played in rounds. Each round, the player sets up the base character — one of eight heroes in the box — and all the equipment this character has. This one character represents every player being a fully-equipped dungeon delver.

The start player (the person who challenged the dungeon last or the last player to be in a dungeon) can choose to draw a card from the monster deck or pass their turn. If they choose to draw, they can do one of two things: (1) keep it and remove a piece of equipment or (2) place it face down in the dungeon. Placing it face down in the dungeon creates the dungeon deck and fills the dungeon with monsters that the challenger will have to face later. If they choose to pass their turn, they cannot participate in the rest of the round. Once only one person is left after all the other players have passed their turn, that player then becomes the challenger and must go into the dungeon with only the equipment currently on the character.

The player then flips cards off the dungeon deck and fights the monsters within. Some equipment allows you to null the enemy damage or be able to withstand it by increasing your HP. If the player survives the dungeon with at least 1 HP, they win that round; if not, they lose. The players then reshuffle all the cards to make a new monster deck and use the same or a different hero to start the boasting once again.

The game ends when someone has won twice or one player is the last person standing.

Dungeon of Mandom VIII includes the material in the original Dungeon of Mandom as well as seven new heroes, seven new monsters, and forty new pieces of equipment, with those items having previously appeared in Welcome to the Dungeon and Welcome Back to the Dungeon.

Codenames: Deep Undercover