Dean cast his gaze to the guard standing at the doorway as he deftly worked the cloth through the loop of the other fabric, pulling the scratchy material tight and knotting it again before pulling at Mills undershirt, ripping another strip off and beginning to tie again.

It had taken a few days with the guards keeping a close eye on him and Castiel, but with the help of Shadson and Mills, they had gathered around twenty prisoners for the escape, gathering all the clothes and bedsheets that they could get their hands on. It hadn't been a hard process to explain the knotting process for them, and although most of the soldiers didn't understand why they needed makeshift rope, or how they were going to get out in the first place, they put their faith in Dean.

It had been surprising for Dean for the others to rely on him so strongly, especially since coming to the camp, he had caused nothing but trouble. Castiel had commented on how it felt almost natural to follow his lead, but Dean pushed that away right then and there. He was not a good person to follow. He was just a man who had a plan in an otherwise hopeless situation.

"You really think this will work?" Mills asked, working on the other end of the rope and looking at Dean with dark eyes. Dean casted her only a small glance before looking back down at the finished knot in his hands, his eyes moving to the sleeping Castiel on the other bed. Shadson had gone to loosen the planks of the other cabins, while Dean and Mills had finished the last rope they had. They only had three with them, but hopefully the soldiers would have been able to rummage up more.

"Not at all," He replied, standing and pushing the rope against the shadow of the bed and lying down, a movement that made it clear that he didn't want to talk until it was time to go. Nevertheless, Mills just stared at him for a moment before sitting across on the other bed, a thoughtful look in her eyes.

"Why do you seem so guilty every time you look at him?" Mills asked, making Dean tense just slightly before he turned away from her, his eyes finding the wall. His gaze subconsciously slid down until he found Castiel again, his heart fluttering in his chest at the strength, yet innocence the man seemed to possess when he was asleep.

"Is it because Sam is there while you're here? Does Castiel remind you of Sam?" Mills asked softly, making Dean furrow his brows and sit up, his eyes widening in alarm as he looked at the woman.

"H-how do you know about Sam?" Dean asked warily, looking at the sympathetic woman. She only sighed, rubbing her hand through her frazzled hair.

"I figured you hadn't remembered me," She stated, giving him a small, sad smile, "I was the sheriff for Sioux Falls. We met quite a bit when you would come over to Bobby's. Then again, that was years ago."

"You know Bobby?" Dean asked, his expression incredulous as Mills nodded, leaning back on her arms and shaking her head, dislodging the hair that was stuck to her face.

"Of course. He always kept me updated on the two of you after I joined the army. You joining the army as well, Sam becoming mute, John's arrest...Sam's letters not going through," She said softly, as if she were trying to guide Dean as if he were a child. Dean swallowed thickly, shaking his head and looking away.

"I didn't want to look at them," Dean said, his voice feeling so much harder to push through. Since when did breathing seem like such a hard task? "I don't deserve to have Sam as a brother. I can't pretend that everything is okay when...for what I did to him..."

"Bobby says that he's always asking about you, figuratively of course," Mills said, her eyes softening as Dean almost recoiled from that look. It was too motherly, and he wouldn't break down here. He didn't deserve to cry for the pain that he had caused.

"It'd be better if he thought I was dead," Dean growled, the words hanging heavy in the air and drawing out a silence between the two of them. It was only broken by Shadson slipping out from under the bed, his eyes glimmering with the strange intellegence he always got when he was doing something sneaky.

"It's time. Two cabins are already led towards the meeting point, so we might want to catch up," Shadson whispered before casting a single last glance to the unaware guard and slipping back into the shadows. Dean sighed and stood, slipping over to Castiel and stirring him away, pressing his finger to the soldier's lips in a way to keep him quiet before getting him up, passing the guidance onto Mills.

"I'll be right behind you," Dean whispered, nodding to her before watching them disappear. He turned to the guard, taking a deep breath and stepping closer, his steps becoming silence as he put to use his sneaking skills, pulling him closer and closer to the guard, his hands pulling up for just a moment before darting out.

His hand closed over the man's mouth and nose, bringing out a soft grunt as the guard was dragged back into the cabin. Dean felt the man struggle for a moment, closing his eyes before gritting his teeth and snapping his neck to the side with an audible crack, slowly letting the man collapse silently to the floor before darting under the bed.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Mills was waiting by the back of the cabin with Castiel, her eyes wide as Dean wriggled out of the space, a single nod between them telling all that needed to be said before he took Castiel's arm, letting her hold the ropes tighter before they slipped towards the interrogation building, where the barbed wire fence met the wood wall, an otherwise desolate building.

There, they already had fifteen men and women waiting for the escape, obvious discomfort on their faces as they constantly glanced around to make sure no guards were after them. Dean patted Castiel's hand once before letting go, Shadson sliding up beside the man to give him the reassurance that there was someone there as Dean took one of the ropes from Mills, hurrying over to the barbed fence.

"Get the ropes around the wire and pull it tight," Dean growled to the other prisoners, throwing his own rope around the bottom two wires several times before pulling it, the wires pulling together and forming a small space. Mills wrapped her rope around the next wire along with Dean's, pulling it ever slightly higher.

The other soldiers began to catch on and used their makeshift ropes to pull the wire tighter and higher up, inching it off the ground and towards the middle of the fence, worry creased in all of their faces as they worked as fast as they could. They would have only maybe thirty minutes before the guards switched post and found the dead guards at the cabins.

The barbed wire was now high enough that a person could get under, even a larger man like Shadson, and the prisoners began flooding the small area before Dean had a chance to say anything. Several got nicks and cuts from the pushing and hurry, but no real damage was done, and the prisoners were darting into the trees as not to be seen, but Dean could still see the movement of them in the shadows, knowing that they were still waiting there.

Mills went first, and Dean helped Castiel through and to her before letting Shadson follow and finally himself. He glanced back, wondering if he had time to pull the ropes off and hide their escape.

A shout from the cabins told them they had no time.

"Go! Part go to the west, another south, and the others to the river," Dean hissed at the other prisoners, watching them quickly split into a group. There was a chance that at least one group would make it, especially with moving quicker through the forest that smaller groups allowed.

Shadson went with the group that headed south, leaving Mills, Dean, and Castiel to follow the group towards the river. They didn't have a plan after that, an escape from the guards that Dean could hear beginning their tyrantal search for the escapees, but just ran.