Booted

Booted is a side quest

Detailed walkthrough
During the Courier's visit to Nipton, they will notice that something is not right. When they first enter the town, they will meet Oliver Swanick, who seems to be over-excited about winning "the lottery" and keeps repeating that he has won. Going further into the town, the Legion has taken over the town and killed almost everyone. While searching through the town, the Courier will find a man called Boxcars in the general store.

Boxcars reacts to the Courier in different ways, depending on their reputation with the Powder Gangers. He tells the Courier about the lottery that the Legion played with the town of Nipton. He then explains to the Courier that some of the Powder Gangers were enslaved by the Legion and taken east. He mentions that his legs are in a lot of pain and he needs Med-X. The Courier then has the option to spare some for him (a choice of up to five doses).

Locate the enslaved Powder Gang members at the Legion raid camp. They are tied up around a campfire being watched by legionaries. Upon freeing the slaves, the legionaries become hostile and will attack if the Courier does not have a positive reputation with Caesar's Legion. It is also possible to untie the slaves while sneaking or wearing Legion faction armor, resulting in the guards remaining friendly. Freeing the Powder Ganger slaves results in a positive increase in reputation with them with no effect on reputation with the Legion (but, as always, killing the legionaries while detected will reduce one's reputation with the Legion). Once the slaves are freed, the quest is completed.

Behind the scenes
"Booted" is the name of a No. 1 1952 song by Rosco Gordon.

Bugs

 * Sometimes, the player character will see the Powder Gangers up and walking freely, they will flee (although not far) if one gets into combat with the legionaries. After defeating the legionaries, the Powder Gangers will keep walking around, when one tries and "talk" to them, they will get an option to untie them or leave them tied regardless of them walking around freely.
 * Sometimes, after killing the Legion guards, the player character cannot untie the Powder Gangers. Waiting a few in-game hours may fix this.
 * Rarely, a Legion guard may be tied up and the prisoner standing next to him. Talking to the guard makes him speak as usual. One will still have the option to untie the prisoner standing next to the guard.
 * If the Courier has ED-E with them as a companion, it may attack the Powder Ganger prisoners and fail the quest. This is more likely if one's reputation with the Powder Gangers is Vilified.
 * Rarely, if one unties one of the Powder Gangers, a Legion guard will take his place sitting on the ground. Talking to the guard offers the same dialogue options as when he is on duty.
 * When reaching the Powder Gangers, they will sometimes appear dead but still be tied up.
 * Sometimes, after freeing the Powder Gangers, they will roam around freely, and after killing all the Legion guards, they will kneel back onto the ground and become tied up again. This time, however, they cannot be untied, though the quest is finished.
 * Sometimes, untying Powder Gangers will not make Legion guards hostile.
 * Sometimes, the Powder Ganger prisoners will walk around freely, but they cannot be untied. They will eventually go back to a sitting position, but they still cannot be untied, i.e. talking to them instead of untying them.