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Central Virginia Regional Jail (or as Chris once called it, "this Jail of Fail") serves five largely rural counties in central Virginia, including Greene County. Chris was sent to the jail following incestuous acts on his mother where he was held without bond from 2 August 2021 through 28 February 2022 - when he was transferred to Western State Hospital - and again from 3 May 2022 until he was released from custody on 27 March 2023.

In an October 2021 letter to a fan, Chris rated the jail accommodations two out of five stars, praising the "mostly good" food, good selection of items in the commissary, and the rec room, and criticizing attitudes from jail jerkops and "really noisy neighbours". In another letter, Chris claimed to have a bidet in his jail cell, possibly referring to the sink/toilet combo common in jails.

Chris was evidently in protective custody as of November 2021, noting in a jail letter that "I do not interact with other inmates often, especially since they've opted to keep me separated from them for my safety."

For activities, Chris mentioned playing solo basketball, listening to the radio, reading, writing, drawing, and placed heavy emphasis on meditation. On 30 November, Chris said in a letter that he had been restricted from the rec room and could no longer play basketball.

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