This quest has many options and will differ depending on what was done and which companions were obtained (if any) before leaving Vault 18. If you have no companions with you, or only Ben Kurtz, this quest is significantly simpler and you can ignore most of the walkthrough.
The quest can be started in several ways: if the Star Player helped defend the vault, it can be started by talking to Kevin Rossman before leaving Vault 18. If the Star Player went through the Enclave questline, it can be given by John Bragg through the Enclave Secure Comlink. If neither option works, the quest will also be started by talking to Ben Kurtz at the end of Blast Radius.
Escaping the vault
After escaping to a safe distance and witnessing the vault's explosion, the "perk" Battle Fatigue will be added, which has negative effects that are removed when the Star Player goes to sleep at Black Bear Lodge.
The first step is to reach Pinehaven. Once there, follow the map marker toward the road going uphill. Along the way, you will find Kira Mann. She is difficult to spot. She is camped at a fire in front of an upturned semi-truck; however, she will likely initiate combat with nearby enemies, resulting in her crouching and hiding near her original position. If the player has Jenn Hail in their party, she and Kira will have an argument as they hated each other in the Vault. Kira will initiate conversation with you almost immediately. Kira reacts depending on how you treated her in Vault 18. If you were a Nerd and were nice to her, or you helped her out as an Athlete by doing the quest I'd Wrestle a Bear for You, you can get her to come with you. Otherwise, she will leave you or become hostile, depending on how you react. A Strength skill of 7 is required if you choose the dialogue option "Well, that's not tasteful..." or a if you choose the dialogue option "Look, you and I...", you will be able to convince her without a skill check.
If have Johnny Matheson is present, he will say that he is feeling ill and proceed to vomit and pass out after reaching the house - at this point the quest There's a Fixer For That will be gained, with objectives to find Fixer and help Johnny. Otherwise, he will die after several in-game hours.
The quest will update again after entering Black Bear Lodge. If Kira or Jamie Campbell are not present, after an NPC dialogue, speak to Ben and jump down to the paragraph after next.
If Kira and Jamie are both present, they will begin to argue. Optionally, a bullet can be fired into the ceiling to intervene, (after a delay, wait for the prompt) or the argument can be allowed to play out. Letting the argument play out will cause Kira to leave, with Jenn trying to stop her and being killed as result, while Eric and Jamie will kill Kira in self-defense. Firing a bullet will result in a Strength check of 7, Charisma check of 7 or Intelligence check of 7, followed by a series of speech checks up to 45. To successfully recruit all the companions, Jenn Hail has a speech check of 40, Jamie Campbell requires Guardian of Vault 18, and Kira Mann requires Nerd-Orable or Smart Jock.
Speak with Ben and exhaust his options. The next step is to look for the Lodge's prior inhabitants. Pick up the notes in the bedroom, visit the cellar, and observe the grave in the backyard. If not already recruited, speak with whichever companions are present. See skill checks above, though Jamie will have an additional option of Speech 55 to recruit her and Eric. Speak to Ben again, who will hint to set mines along the road and the ridge of trees by the cliff for an anticipated attack.
Complete "There's a Fixer For That" if it is active before going to bed. Any companions not recruited will leave when you sleep. Once you go to bed, the Battle Fatigue perk is removed.
When the sequence finishes, Ben wakes you up to warn you of an attack by a group of Survivalist Raiders, lead by Captain Jackson. You have the option of surrendering to him or killing him. Either way, this ends the quest and starts Lost Roads. If Captain Jackson is successful in capturing you, the quest Hell's Gate begins.
Some weapons, when fired into the ceiling during the companion argument, may not have any effect or update the quest. All ballistic weapons are known to work, however.