I want to call this episode “bittersweet,” but that doesn’t seem to do it justice.

Kevin’s hearing Crowley’s voice in his head and is understandably on edge, but he’s figured out the second trial: Sam has to rescue an innocent soul from hell. How does a mortal get into hell? Sam and Dean start by summoning a crossroads demon and torturing him for information. The demon cracks, and it’s off to find a reaper who knows all the secret passages into hell.

That reaper is a taxi driver named Ajay, who also happens to be the reaper who escorted Bobby Singer to hell. Bobby made it into Crowley’s burn book, so innocent as he was, it’s hellfire for Bobby. This conveniently takes care of the which-soul-to-save bit. With the Winchesters in debt to him, Ajay takes Sam on the back roads to hell. First stop? Purgatory.

Ajay leaves Sam with 24 hours to find the portal to hell, get Bobby, and meet him back in purgatory. Get in, get out, go home. As if. Between Kevin’s work and the hellhound Sam killed, Crowley is suspicious. He pops up in Ajay’s backseat and grills him for information. He spills, but he still pays the price of his life, leaving Sam with no way out.

Meanwhile, Dean’s been trying to talk Kevin down a bit. At first, he’ll barely come out of his room, and then when he does, it’s to hide the tablet – and he won’t tell Dean where. And maybe Kevin is right to feel unsafe, considering how easily Naomi gets into their hideout. (To be fair, it’s not protected from angels because, as Naomi points out, Dean hopes Cas while show up). Naomi comes to Dean to insist they’re on the same side, though he, of course, has a hard time believing that, considering what she did to Cas.

But that’s the least of his worries when he finds Ajay dead. In order to pull his brother back out, Dean calls up an old friend to make a desperate request.

Unaware that his ride is gone, Sam has found the portal and made his way into hell. When he finds a haggard Bobby in an unlocked cell, the first thing Bobby does is punch Sam in the face. But you have to understand, Bobby’s hell has been black-eyed Sams and Deans constantly coming for him. However, once Sam divulges some of Bobby’s most sinister secrets – his fondness for Tori Spelling and pedicures – they have their brief reunion, then fight their way back to purgatory.

Up top, Dean is asking Benny for the ultimate favor – letting him send Benny back to purgatory to get Sam and Bobby out the way Dean and Benny had gotten out. Benny has never looked more like a brother to Dean than in the final heartbreaking scene they share. Benny agrees to let Dean behead him to get him back in, saying he felt he didn’t fit in anyway, with humans or vampires. The intention is to have Sam bring back Benny as well as Bobby, but you can already sense the finality in Dean and Benny’s goodbye.

Benny’s just in time to help Sam and Bobby get out. Sam’s got Bobby settled as his carry-on in his arm, and is ready to take Benny too, when a group of vampires shows up. Benny goes to fight them off, telling Sam to tell Dean he says goodbye. Sam sees him go down as he gets pulled through the portal.

Dean’s waiting in the woods for Sam and his relief to see his little brother safe is palpable. They start to release Bobby’s soul into heaven when Crowley comes to ruin the moment. I was genuinely stumped for moment on who was left to save them. That’s when Naomi showed, warding Crowley off and reclaiming Bobby’s soul for heaven. How’s that for a twist? Mixed feelings, anyone?

Once Sam finishes the second trial and the brothers are out of the woods, they’re still not… you know… out of the woods. When they get to the hideout, Kevin’s gone, and so is all his work. Dean thinks he’s just finally snapped and took off, but the last time we see Kevin, he’s facing Crowley, who tells him his mother was killed because she wouldn’t give him up. So was Kevin running from the Crowley in his head, or is the king of hell getting some advanced placement tutoring?

We’ve got another break coming up, but when Supernatural returns on April 24, Charlie is back!

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