The Courier needs to play the games that the casino has to offer (Blackjack, Slots and Roulette) until they are banned from gambling in the casino. The player can be banned by winning too many games and getting too much money from the casino. During this process, the Courier will be receiving three different prizes from the casino. Each prize will be given after the player win a certain amount of money while gambling. These prizes are usually given by the table manager of the casino.
Before the Courier manages to start gambling in the casino, they will need to re-open it. The player can re-open it by disabling the security holograms and by activating the dealer holograms.
As the Courier wins the games in the casino, they will receive the following rewards, collected from the casino cashier:
After winning 10,000+ chips, the Courier will be banned from playing games in the Sierra Madre casino. The player can still use its other functions, like the bar, but they cannot gamble on its tables anymore. This ban is permanent.
If the player breaks the house limit before getting any comp gifts (by getting a large win), they will not receive any comps they have missed.
Unlike other casinos, the Sierra Madre will exchange chips for Pre-War Money at a 1:1 ratio. This is a useful way to generate a large amount of weightless goods, to sell once leaving the DLC.