"Kevin, open up! Kevin!" Dean pounded on the metal door of Garth's houseboat. Kevin opened the door, a huge cast iron skillet in hand, looking haunted, tired and unkempt. "Whoa! Whoa. Geez. What's going on? What's with the S.O.S?" He entered the room, Sam and Mack close behind. "It's him," Kevin answered. "It's who?" Sam asked. "Crowley." Mack had been looking around the small space curiously, but turned her attention to the older boy when he said the demon king's name. "What about him?" Dean pressed.

"He's in my head."

"He's… in your head," Sam echoed slowly. "Do you know what that means?" Kevin demanded. "Yeah, it means we need to up your anxiety meds," Dean nodded. "Kevin, you're dreaming. Look, if Crowley knew where you were, he'd do a hell of a lot more than mess with your head."

"Where's Garth?" Mack piped up curiously. "On a case, or- or the dentist," Kevin shrugged. "I don't know. I haven't heard from him." Sam and Dean exchanged a look. "Okay, well, what did you want to tell us that you couldn't say on the phone?" Dean asked. "Would you put the frying pan down, please?" Kevin complied, placing the skillet on the stove. "I translated the second trial from the Tablet," he informed them. "You… crazy Prophet, you. Nice work!"

"And if Crowley's in my head, he knows."

"Okay, he's definitely not in your head," Dean groaned. "He's not in your head, Kevin," Sam chimed in. "It's okay. Just… We know you're distressed. Just stay with us, alright? What's the second trial?"

"An innocent soul has to be rescued from Hell and delivered unto Heaven."

"What?"

"'Unto'," Kevin repeated, misunderstanding Dean's confusion. "That's- that's how God talks." Sam knit his brow together, stammering. "Rescue a soul from Hell? Like actually… Go to Hell? How- how do you get a soul unto Heaven? I mean, how do you even get a soul out of Hell?"

"We're gonna need an expert," Dean mused.

After the crossroads demon they summoned told them how to find a rogue reaper who could smuggle them into Hell, they tracked down a reaper posing as a taxi driver. "Ajay," Dean greeted the reaper. "Need to talk to you for a second." Ajay removed his Bluetooth headset, staring at the Winchesters with wide eyes, "You know my name."

"And what you do," Sam added. "We want to do business." Ajay frowned. "But you are mortal- flesh and blood." Mack bit her lip, clutching Dean's hand tightly as Sam continued. "But if we wanted to cross the border into Hell-"

"Visitor's pass," Dean finished. Ajay scoffed, "No one wants to get into Hell." Sam pressed, "But a coyote like you could do it?" Ajay studied the trio for a long beat and then nodded his head slowly. "It's possible. But I have special skills. I have overhead. It will be pricey." Mack looked up at Dean worriedly. He was frowning at Ajay. "How pricey?" he asked. "You two are resourceful," Ajay shrugged, leaving Mack out of it. "One day, you will owe me a favor."

"You say that like you know us."

"Of course," Ajay smirked. "You're the Winchesters." Dean's frown increased, "I'm sorry, have we met?" Ajay stared at him straight in the eyes. "I'm the reaper who took Bobby Singer to Hell." Beside Dean, Mack went stiff and the brothers both stared at the reaper in shock. "Bobby in Hell?" Sam echoed. "We burned his bones. Once we did that, it was over. End of story." Ajay shrugged, "Hmm… Not necessarily."

"No, no, no, 'cause, see, Bobby was on the good side of things, and good guys go to the penthouse," Dean argued. "Usually, mostly," Ajay bobbed his head back and forth. "Depends on who you know, what palms get greased. If you're on the king of Hell's no-fly list, no way you cruise the friendly skies." All three Winchesters were livid. "Crowley," Dean growled. "Okay, let's do this. How much for three tickets down and four back?"

"Dean."

"What?"

"Come here," Sam nodded and Dean rolled his eyes, following him away from Ajay. Mack kept glancing nervously back at the reaper. "What the hell are you thinking?" Sam hissed. "You heard the guy- Bobby's in Hell. We're gonna spring him." Sam huffed in annoyance. "We've gone over this, Dean. I have to do the trials solo." Dean shook his head. "This is Bobby we're talking about, Sam," he argued. "Now, let's face it- you have not exactly been up to full speed lately, okay? We got one shot at this. We can't miss."

"I'm not gonna miss," Sam opened his jacket, revealing Ruby's knife in the interior pocket. "I'll bring him back." He walked back to Ajay. "I'm in. Just me." Ajay smiled. "Follow me." Dean and Mack came back over. "Wait, wait, wait, wait, wait, wait. How does this… work?" Dean demanded. "Not to fret. He'll be back in exactly twenty-four hours time. Return for him then." Ajay led Sam away. Dean glanced at his watch, then down at Mack. "Come on, bug."

They headed back to the Impala, stopping to grab some food before taking it to Garth's houseboat to check on Kevin. "Yo, Kev! It's me and Mack!" Dean called out, carrying the tray of take-out in one hand. "Kevin!" The closet door opened a crack, Kevin speaking from the doorway. "I believe the closet would be safest." Dean frowned, setting the tray of food down. "Safe from what?" he asked. "Crowley. He's in my head, Dean. And if he's in my head, he knows where I am! You know, we- we should move out. We'll find another place."

"Jeez, Kev. Would you chill out?" Dean sighed, handing Mack her food from the tray and then turning back to the older boy. "Have a burger. Come on. Don't lose it on me now dude." Cautiously, Kevin exited the closet. "There you go. That's it." Mack stared at the burger in front of her, chewing her lip and not touching the food. "Just tell me when this all ends, 'cause that's the only thing I want to hear," Kevin requested. "No, like I told you before, this isn't going to end," Dean answered. "Look, man, other guys, they got it easy, you know? It's all backyard barbecues and… bowling teams, but you and me? We got to carry a little extra weight."

"I can't take it."

"Yes, you can. Hey, look at me," Dean said, using his Dad voice and waiting until Kevin complied to continue. "Now, this whole thing sucks. I know. But you suck it up and you push through because that's what we do. And when you get on board with that, the ride is a lot smoother. French fry?" Kevin looked at the food for a moment. "I'm gonna- I'm gonna be in my room. Let me know when there's a good day." He grabbed the entire tray of take-out, including Dean's meal, and went back into the closet, shutting the door. "That's my pie," Dean frowned.

"Daddy?"

"What, bug?"

"Is Uncle Sammy gonna be able to save Grandpa Bobby?" Dean swallowed, glancing over at his daughter from his position by the stove. He'd found some eggs and bacon and was working on frying them up since Kevin took his food. Ever since Cas saved her from Naomi, Mack had been a lot more clingy to him. She hadn't brought up wanting to go off on her own again once, which was fine by him. After she had gotten past the initial shock of being back at the bunker, she'd told him specifically what had happened while he held her in her bed. "Yeah, baby, he is," he answered. "Don't worry. It'll be alright."

She nodded, laying her chin down on her arms folded on top of the table. "Hey, Kevin!" he called out a second later. "Come in here and grab some of these eggs. Kev! Come on man. You can't hide in there forever." Instead of coming out of the closet, Kevin entered the room from the main door. Mack raised her head, staring at him in surprise. Dean also gaped over at him. "Where the hell have you been? What happened to being scared?"

"I am scared. So I made a preemptive move."

"So… Made a what now?" Dean demanded. "I can't sit here with the Tablet like a… sitting duck and Crowley breathing down my ass. Getting rid of the Tablet just takes off some of the pressure." Dean blinked. "Wait. Getting rid of it?" he queried. "Temporarily," Kevin shrugged. "I hid it."

"What? Where?"

"If I tell you, it's not hidden, is it?"

"Kevin, tell me where the damn Tablet is, or I swear to you-"

"You'll what, Dean?" he asked, heading into his room and shutting the door without another word. "Kevin!" Dean yelled, moving toward the door. "Kids," a voice said behind him and he turned to see a woman in a gray pantsuit. "So cute when they're little. Then they turn into teenagers, and the party's over. We haven't been formally introduced, Dean. My name's Naomi." She stuck her hand out to shake, but he backed away from her. Mack had scrambled up from the table, whimpering as she hurried over to hide behind him from the angel.

"Oh, I know who you are," Dean spat. "And I know what you did to my daughter. And Cas after he got out of Purgatory." Naomi retracted her hand. "After I rescued him from Purgatory, you mean," she corrected, ignoring his comment about Mack, "at the cost of many angels' lives." Dean continued to glare at her, hyper aware of Mack's tight grip on the back of his jacket and her erratic breathing as she hid from Naomi. "You screwed with his head and had him spy on us."

"Well, it is true that I have spoken with Castiel many times, trying to reach out to him, trying to help him. Dean, you must have noticed how Purgatory changed him. I mean, he's been unstable in the past, but I was shocked at how damaged he is now." Mack whimpered again, pressing closer to Dean. "Stop, okay?" he snapped. "Don't- don't try to spin this. You think I don't know that you told him to try and kill me? That you threatened to kill my kid if he didn't?"

"Hmm. Yeah, I suppose that is how he would hear it-"

"That's how Mack heard it," Dean growled. Naomi paused, rolling her shoulders back and setting her jaw before continuing. "When I heard of the Angel Tablet, I did tell Castiel to get it at any cost. That's my job- to protect Heaven. I'm a warrior, just as you are. What would you expect? And now Castiel is in the wind with a hydrogen bomb in his pocket, and I- I'm scared, for all of us."

"Save it. See, I don't trust angels, which means I don't trust you."

"And yet you have not warded this place against us. I know. You're hoping Castiel will return to you. I admire your loyalty. I only wish he felt the same way," she grimaced. "I know you don't want to believe it, Dean, but we're on the same side- shutting the gates of Hell, bringing Castiel in from the cold. Take a moment. Think about what I've said." Dean continued to keep his face completely stoic, not revealing how her words were getting under his skin. "Oh," she added as an afterthought. "I know you've been doing business with Ajay. He did mention, didn't he, that his way into Hell is through Purgatory?"

Dean's stoic demeanor dropped for a second in surprise and she smirked. "I knew you'd want to know. You see, we can be of help to each other." She vanished with a flap of her wings. "Daddy-" Mack started, staring up at him with fearful eyes. "We gotta go," he murmured.

When they got back to Ajay's taxi, the reaper was dead in the front seat. Mack was fighting to keep her breathing under control as Dean pulled his phone out. "Yeah. Hey, it's me," he said. "I know. I know, man. It's been a long time. I mean, I wanted to call. I did. I just, uh… I thought it might be better if I didn't…" He glanced over at Mack. She had sunk down into a sitting position against a nearby building, whimpering and rocking with her eyes screwed shut tight. "How you been?" he asked Benny as he went over, placing a hand on top of Mack's knee. She opened her eyes, stopping her rocking motion and staring up at him. "I guess I let you down, huh?"

He rubbed his thumb comfortingly on Mack's knee, silently letting her know he was there for her as he continued to address Benny. "You might change your mind on that. Benny, I gotta ask you a favor. It's a big one."

Dean hugged Mack tightly against his chest as Benny's beat-up old camper pulled into the alley beside the Impala. She hadn't stopped freaking out since Naomi's surprise appearance at the boat. She had cried herself to sleep in his arms back at the motel they'd gotten while they waited for Benny to arrive. "If you want nothing to do with this, I completely understand," Dean told Benny as the vampire approached them. "Wow," Benny replied. "When Dean Winchester asks for a favor, he's not screwing around."

"Benny, sending you back there is the last thing I ever wanted to do."

"I know. I know."

"But my little brother is stuck down there," Dean added. "This would be the same little brother who wants to kill me, right?" Benny clarified. "You got access to the place," Dean murmured. "By 'access', you mean 'getting beheaded'?" the vamp translated. "Yeah, you're right- it's too much," Dean sighed, tightening his hold on Mack. "It's not like I've exactly been there for you lately." Benny blinked. "What? Oh, come on, Dean. You know I love a challenge."

"You're serious?" Dean asked. "Hey, he's your brother. I say let's do this." Benny lowered his gaze to the young girl in Dean's arms, then looked back at Dean. "She okay?" Dean bit his lip, "It's been an exhausting twenty-four hours." Benny nodded in understanding. "I owe you," Dean added. "Oh, you don't owe me nothing. Truth is, uh… I could use a break from all this." Dean frowned, "It really been that tough?"

"I'm not a good fit, Dean. Not with the vampires, and, for sure, not with the humans. I don't belong. And after a while… that starts to wear on you," Benny scoffed at Dean's expression. "Right? Cry me a river. Like you need to listen to this."

"Well, when you get back up here, we're gonna fix all that, okay?"

"When I get back?"

"Yeah, you find the portal, and you ride out of Purgatory with Sam just like you did with me, okay? As soon as I send you back, Mack and I are gonna haul ass to Maine, and we're gonna be waiting for you as soon as you get topside."

"Yeah," Benny nodded. "That sounds like a plan, chief. Let's get on with it." Dean swallowed, "You sure about this?" Benny scoffed again. "Not my first rodeo, man." Dean gently coaxed Mack away from him so that he could circle around to the trunk and grab a machete. "Come here, sister," Benny said, pulling Mack in for a hug. "I promise you, I'll get your uncle back safely, alright? You just look out for your daddy for me, ya hear?"

"Thanks, Benny," she murmured, hugging him back tightly. She let go, allowing her father to take a turn, he and Benny clasping hands to shake before pulling each other into a hug. "Thank you," Dean told him, pulling back. "Well, come on," Benny smirked. "You a wimp?" Mack flinched as Dean swung the machete, sending Benny's head rolling.

Dean and Mack were making their way through the woods in the hundred-mile wilderness in Maine near where Dean landed nearly a year prior. Suddenly, there was a flash of light nearby and Sam was suddenly standing there, stumbling over to where they were. "Uncle Sammy!" Mack cried, hugging him tightly. "Hey, Kinley," Sam smiled, hugging her back. She pulled back, allowing him to hug Dean next. "Purgatory, right?" Dean smirked. "A real garden spot, ain't it?" Sam nodded, "Yeah."

"Did you get him out?"

"Only Bobby." Dean raised his eyebrows. "What? I mean, that's fantastic about Bobby." Sam grimaced. "Dean, look- Benny, uh… He got us out. A bunch of vamps showed, and he used himself as bait. I get the feeling even if that didn't happen, he didn't want to come back, you know? I'm sorry." Dean frowned, glancing down, "You're probably right. So, uh… Bobby- how- how'd he hold up down there?" Sam smiled a little. "He's good, all things considered. Ornery as hell, of course."

"As he should be. Let's put that old man where he belongs."

"Yeah," Sam pulled up his jacket sleeve, knife in hand. "Solvo haec phantasmata in terram," he recited, the yellow and red light of Bobby's soul glowing and writhing beneath his skin, "et inde ad olympum." He held his arm up, the light turning bluish-white as Bobby's soul left his arm and started rising up toward the sky. Suddenly, it turned into a cloudy mix of red and black, stopping midair. "What the hell?" Dean asked.

"Hello, boys. Chipmunk." The Winchesters turned to face Crowley as he looked up at the red and black cloud of light in the sky. "Bobby Singer- I'd know you anywhere." Mack was the one to pipe up. "Let him go, Crowley. He doesn't belong in Hell." Crowley smirked at her, "He does if I say he does. He's inflicted untold damage on my kind. From where I sit, actually, Hell's too good for him. Really?" Sam and Dean had started to rush toward the demon, but with a flick of his finger, Crowley had pinned all three Winchesters to separate trees several feet off the ground. He looked at Bobby's soul, which had started to come back down towards the Earth.

"What?" he demanded when it stopped again, flashes of white light shooting through it. He turned to see Naomi standing there, a pleased look on her face. "Oh, come on!" he cried angrily. "Let me see if I've interpreted the situation correctly," the angel began. "The Winchesters have freed an innocent soul from Hell, to which you are wrongfully trying to return it."

"Siding with them, Naomi? You don't know those three. Before they're done, we'll both be locked away," Crowley said. "I'm just hoping they lock you away, dear. The rest I'll figure out," Naomi smirked. "Bureaucrat," the demon spat. "You're fighting outside your weight class." The angel's eyes flashed with anger. "Don't call me a bureaucrat." She raised her hand toward him, eyes shining brightly with grace. Crowley vanished then, and the Winchesters all plummeted to the ground. Dean immediately rushed over to help Mack to her feet. She clutched his arm, staring at Naomi fearfully.

She had redirected her hand upwards, sending Bobby's soul shooting upward in a flash of blue and white light. She turned her focus toward Dean. "I told you you could trust me." She vanished. "What the hell was that?" Sam demanded. "I'll tell you later. Let's get this trial done." Sam took out the paper from his pocket, intoning the Enochian phrase. "Kah-nuh-ahm-duhr." He grabbed his right arm, falling to his knees in agony. His hand looked like it was burning on the inside, and he made a fist as the light faded. Dean grabbed onto his shoulder.

"Sam? What? What?! Talk to me! What?!"

"It's okay!" Sam panted. "It's okay! It's okay. I'm fine. It's done. It's done."