It was Chief Judge Diane Wood who most clearly signaled she believed the detectives went too far, including by quoting a Biblical passage that the “truth would set him free” to suggest Dassey might be released if he confessed and by winning his trust by saying they were talking to him more as parental figures than as cops.

Video of the interrogation shows one detective saying he’s a dad to a child around Dassey’s age, adding, “There’s nothing I’d like more than to come over and give you a hug cause I know you’re hurting.”

“The investigators made my skin crawl watching this video,” Wood said. Wood noted that Dassey had no one representing him in the room and appeared disoriented, pausing for long stretches.

“He is obviously racking his brain about how he can answer … in a way (investigators) will like,” she said.

Dassey has a low IQ of around 80 and struggles to grasp simple concepts, meanings and consequences, court filings say. Wood said comments by Dassey during his interview strongly suggested he didn’t understand what was happening. After appearing to confess to participation in a brutal slaying, she noted, he asked the detective if he could now go back to school.