| How the Fuck Can You Grin?|
Complete the Golden Grin Casino heist on the Death Wish difficulty or above.
| Blind Eye in the Sky|
Complete the Golden Grin Casino heist in stealth. Unlocks the "Wheeler Dealer" mask, "Stars" material and "Chips" pattern.
| City of Sin and Well-Oiled Gears|
Complete the Golden Grin Casino heist without having the Big Fucking Drill ever break in loud. Unlocks the "Murmillo Galea Helmet" mask, "Casino" material and "Royale" pattern.
| High Roller|
Complete the Golden Grin Casino heist under 14 minutes. Unlocks "The King" mask, "Plush" material and "Cards" pattern.
| Hail to the King, Baby|
In the Golden Grin Casino heist, kill "The King" and complete the heist in stealth. Unlocks the "Sports Utility Mask" mask, "Carpet" material and "Dices" pattern.
The following appeared on June 22, 2015. They were replaced on June 25, 2015.
| Luck Is|
| What Happens|
| When Preparation|
- The teasers is a quote from The Dentist during pre-planning, also referencing that he first offered preplanning first in his heists.
- How The Fuck Can You Grin? is a quote from the film Casino.
- The name of the mask and material unlocked with the City of Sin and Well-Oiled Gears achievement is most likely a reference to the 2006 James Bond film, Casino Royale.
- A High Roller is a gambler who wagers large amounts of money.
- Hail to the King, Baby is a quote from the film Army of Darkness, which would go on to be quoted by Duke Nukem.