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Dylann was placed in the Al-Cannon detention centre following his arrest. According to fellow inmate Ashley Ireland, Dylann had stacks of mail in his cell every day. But he never seemed to read any of the letters. He said that Dylann read the bible every night in his cell, but when Ashley went to ask him what bible verse Dylann was reading he realized it seemed as if Dylann didn’t know anything about the bible. Ashley said “He didn't really understand what any of it meant. I don't think he was even really reading it.” Ashley said that Dylann seemed to be lost and hopeless. Dylann once confided in him that he wished he hadn’t of done it and that he didn’t even know why he did it. He said that he didn’t want to die but he couldn’t have certain people thinking he was insane. Dylann got an hour of recreation a day, during this time everyone else had to stay in their cells. But Dylann only used up 15 minutes of his time were he got stuff from the canteen and showered. When Ashley asked why he didn’t use much of his recreation time Dylann said he didn’t want to take away from the free time other people could be using.

Dylann and Dwayne Stafford seemed to have gotten along at first. Dwayne said that they would engage in conversation about politics and current world events. But sometimes would also talk about girls. Dwayne said he would often go up to Dylann’s cell door to ask him what was up and he said that Dylann would come up to the cell door smiling. It’s not completely known what exactly caused their “friendship” to end. But Dwayne said that he had pressed Dylann on his plans to start a race war and that lead to Dylann insulting Dwayne’s recently deceased father. Dwayne also mentioned that Dylann was telling other inmates about how he had killed a child, which Dwayne corrected him by informing him that the 11 year-old girl actually had survived Dylann’s attack by playing dead.

On August 4th, Dwayne Stafford managed to get out of his cell during Dylann’s shower time. He ran down to the shower room unnoticed as guards were preoccupied with other things. Dylann was about to get in the shower when Dwayne punched him multiple times. Dwayne said Dylann had attempted to fight back but was unable to. Guards managed to break the pair apart quickly. Dylann was found bloodied but was relatively okay. Dylann did not press any charges against Dwayne for the assault.

Dylann had a jailhouse journal that was confiscated after he had tried to send his sister a letter that seemed like he was suicidal. Dylann cleared up some things that he alleged was untrue. He said that he had never intended to kill the young girl in the church and that he had never aimed at her. He also cleared up a rumour that had been circulated by a journalist that falsely stated he had committed the attacks after his girlfriend left him for a black man.

Dylann had many bizarre interactions over jailhouse video. On one occasion, his grandfather asked him if he had a chipped tooth. Dylann responded “No, they are just crooked.” His grandfather said that they needed to get him an orthodontist, to which Dylann bursted out laughing and informed his grandfather that there was no orthodontist in jail. He continued by detailing how terrible the dental care is in jail, stating that “they pull out teeth for the slightest problem.” His grandparents were visibly distressed.

Dylann has described himself as enjoying messing with others, and others have said it seems he enjoys to as well. On one occasion he had tried to trick his mother that he had tinsel in his cell. As well as inquiring about his cats to which he berated his mother for feeding them too many treats.

He even cried in one video, convinced he had syphilis despite the fact that he says he has never had a girlfriend. He often makes statements that upset his parents, he told his father that he was thinking of doing something even worse than the court massacre. His father teared up and told him “You know that everything you've done is a reflection on us as a family. Don't be a fucking dumbass.” But sometimes him and his father would make jokes about how much money the government was wasting on him. His mother tried to convince him to keep his lawyers, to which he refused and told her “Don’t trust my lawyers, they’re tricking you.” He engaged with small talk with his younger sister Morgan, he asked her what she wanted to do as a career. She replied Nurse to which he scoffed at the unoriginality. He stated he no longer has to worry about making a living since he is in prison. His sister smiled back calling him “A professional dumbass.” In the video call between his father and younger sister, she also asked him if she could attend his execution to which they all laughed and he told them he can only invite two people.

His sister Amber told him on call that she was angry with him, he laughs and says “Well this isn’t a good visit.” She tells him he is way too happy for her to feel ok about him. He responds by saying “I still have 19 minutes to start crying.” He only apologized for ruining her wedding when she directly asked him to. Amber tells him he is going to be an uncle. He responds by asking if it was too late to get an abortion.

He was very against the idea of these videos being released and told his younger sister that he was trying to stop them from doing it. He felt that the release would be an invasion of his and his family’s privacy. He says that it has been difficult to talk to his parents about the crime and explain why he did it to them knowing the videos may be released.

Dylann received a lot of fan mail as mentioned before. He had a call of a romantic nature with a woman on two separate occasions, who was sort of courting Dylann trying to be his long distance girlfriend now that he is in prison. In the call, he told her “I can’t talk to you. These videos will be part of the trial. I can’t do that. You have to go away.”

In 2020, Dylann reached out to the Associated Press alleging that he has been targeted by staff and treated disproportionately harsh and he went on hunger strike due to the mistreatment. A person familiar with the matter informed them it had ended, it’s not known exactly how long it lasted. But Dylann said that he was several days into his hunger strike. His protest ended when corrections officers forcibly tried to take his blood and insert an IV into his arm, which caused him to briefly pass out. Dylann said the he felt as though he could have went much longer without food but said “It’s just not worth being murdered over.”