Optional missions from your underbosses have five instances. You unlock one instance by default, and two instances per district assigned. So to get all optional mission instances for all your underbosses, you have to divide the 9 districts (the Bayou is free) equally among them. Equally dividing the districts also ensures that they'll remain loyal to you and won't rebel against you. Loyalty is also increased by completing these optional missions for them.
Talk to Cassandra to start a cutscene. You’ll then need to hijack trucks full of weapons and deliver them to one of Cassandra’s rackets. Head to the truck’s location and clear it off enemies. Once done, drive the truck to Cassandra’s shop in the Hollow. Talk to her to complete the mission.
After giving another district to Cassandra, she’ll have more weapon hijacking targets for you. You have to steal another weapon stash truck from the Dixie Mafia location in the Bayou. Like before, deliver it to Cassandra then talk to her to complete the mission.
Talk to her again to start the third run for this mission. This time, she’ll ask you to steal a police truck in the Southdowns. When you arrive, you’ll see a couple of Dixie Mafia talking with the corrupt police. If you wait, they’ll leave. Now the zone where the truck is located has several police officers but it’s not a restricted area so you can sneak inside and take the truck.
Now the problem is how to bring it back to Cassandra. If police on foot or in patrol cars spot you, they’ll immediately start a chase. If you haven’t used a marker from Burke, you should be able to use the Police Dispatcher associate to get off some heat from you. Or, you can let the police give chase and lure them to the nearest friendly hideout (I chose the nightclub) then hide inside until the zone turns to blue then use the police dispatcher favor to drive away the police. This way, your chances of delivering the police truck without encountering a police vehicle will be low.
After assigning the third district to Cassandra, she’ll send you to two more weapon shipments you can steal. The next one is located in the Tickfaw Harbor. Head there and kill all enemies then drive the truck all the way back to Cassandra’s hideout.
For the last target, you have to head to the weapons warehouse in the northern tip of Bayou Fantom. There aren’t that many enemies but you have to be careful of the two snipers on the rooftops. Make sure to get rid of them first, silently if you can, then slowly decimate the enemy numbers outside.
After clearing the warehouse, ride the truck then deliver the truck in one piece to Cassandra. Talk to her to complete her optional mission. You'll also unlock a corresponding trophy.