I have a party of 4 players.
Last session, one player was unable to attend. While I was sort of uncomfortable running a game without another player (I've done this in the past) all of the other players heavily insisted on playing, including the absent player.
The players were in prison. I set the absent player in solitary confinement for having contraband he had requested in the previous session. My other players in prison were chosen to participate in a skill challenge that actually killed both of them.
At this point, 2 players are dead, 1 player is is not in prison, 1 player in solitary confinement.
At this point I considered wrapping up the session. My two other players already had new characters made and were excited to play them. Eventually, we began anew. My three players at the table stayed away from the prison; only one had any kind of reason to stay near the prison and try to bust the last one out.
I've put myself in a corner and need a bit of help. It's been the first game I've run (if that's not too obvious) and am having a difficult time figuring out how to bust out the last player.
My 3 other party members are quite a ways away from the prison at this point.
The party: Bard, college of swords; Fighter; Ranger; Arcane Trickster Rogue in Prison. The prison suppresses magic. The three out of prison are about to enter a dwarven city with quests there.
Essentially each party members backstories are as follows:
Bard (Half-Elf) — Wishes revenge upon her uncle who murdered her aunt. Her aunt is who taught her how to play her first instrument and showed her the path of an entertainer. She joined a circus that has been prominent in the world and experienced more betrayal through the ringmaster who still runs the circus.
Fighter (Human) — A sailor who was a privateer on a ship on contract from a large trade company. An accident occurred and his ship sunk a civilian boat and killed all 9 civilians on board. The trade company heard of this and ripped all funding to his ship and eventually attacked. The fighter was the only survivor.
Ranger (Human) — A homebrew wraith infused ranger almost identical to Talon from Shadow of Mordor. On his travels alone he was resting near an unmarked gravesite and his soul was bonded with this spirit. His personal journey is finding out who this wraith is and why he's chosen him to bond with. I've had more time working with this character and have been doing dream sequences to reveal more of the wraith's past to the ranger.
Rogue (Halfling) — He was exiled out of his hometown while a "cleansing" was taking place. The town was in the process of effectively removing all traces of magic and evidence of races that were not human or half-elf. He desperately tried to save as many books and manuscripts as he could, saving the knowledge of his master's work. I have a quest on deck for this character of his teacher being alive and having a gift for him somewhere.
Should I have someone bail out the last one but offer a quest as ways of repaying the debt?
Should I just have him be acquitted?
Should I have downtime for all players so the sentence is served (2 years)?
I'm looking for the best way of bringing the party back together again.