- "Now hit it hard and the punk ass security cars should bail."
- ―Joey Leone.
Claude goes to Joey's garage in Trenton and Joey explains that they are planning to hit a Securicar pay role van. Joey instructs Claude to find a vehicle and ram the van until the driver bails out. Joey then instructs Claude to take the van to a warehouse in Portland Harbor, where some accomplices will get to the cash. When the mission begins, the Securicar is on the move on the edge of Chinatown.
The first objective is to damage the Securicar (indicated by a Damage meter) to the point where its occupants must bail out, as the van's door are locked. Because this particular Securicar is bulletproof, the player must ram the vehicle continuously until the damage meter is full; large and heavy vehicles such as the Bus, Coach or Linerunner are particularly useful damaging the Securicar quickly and pinning down the van when necessary. Upon ramming the Securicar for the first time, the van will begin to flee. In addition, the player accumulates a minimum of two stars by only hitting the vehicle twice.
When the Securicar is sufficiently damaged, its occupants exit the vehicle and flee, allowing the player to commandeer the van and take it to a garage in Portland Harbor. Even if the player has up to three stars, the Securicar's weight should allow the vehicle to push aside any opposing police cars. Regardless of how many stars the player has, their wanted level is nullified when the Securicar reaches its final destination.
- The skins of the van's motorists are unique in the game. They use a cap and shirt in which it is written "Fort Inox Security".
- The best way to damage the vehicle fast is by using a big vehicle like the Pony or the Moonbeam.
The reward for completing the mission is $20,000 and the unlocking of two missions: Cipriani's Chauffeur and Turismo. In addition, the garage used to stash the Securicar in "Van Heist" may receive additional Securicars thereafter, with payouts for every additional Securicar delivered decreased by $500 until the player may no longer receive any more money.