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October was the tenth month of 2021. Chris remained in jail for the entire month, waiting for his delayed second court appearance in November. Continuing on from the previous month, Chris wrote several letters from jail.
- 1 October - Barb turns 80. With Bob long-dead and Chris in jail, it is her first birthday in decades spent completely alone.
- 3 October - Chris begins writing a letter to a ween in response to an apparent attempt to convert him to Islam.
- 4 October - Chris finishes writing the Islam letter, then begins another letter shortly afterwards, this one directed towards Kenneth Engelhardt.
- 5 October - Chris finishes writing the Kengle letter.
- 6 October - The Kengle letter is sent in the mail.
- 7 October - The Islam letter is sent in the mail.
- 10 October - The Kengle letter is received and uploaded online.
- 13 October - The Islam letter is received and uploaded online.
- 21 October - Chris writes another letter, responding to an inquiry about a plush doll seen in some of his videos.
- 22 October - The plush doll letter is sent in the mail.
- 25 October
- 26 October - The Virginia fan letter is sent in the mail.
- 27 October - A fan named Cory Allison writes Chris a letter and includes his phone number.
- 29 October - The letter from October 25th is received and uploaded online.
- 30 October - Chris writes a third letter addressed to Kengle.
- 31 October - Halloween. Chris called Cory from the jail phone but caught him while he was at work, so the call was cut short and not recorded. Meanwhile, no trick-or-treaters showed up at Barb's door, so she spent this day in complete isolation.
- https://twitter.com/terrybeigie/status/1438504504396161029 (archive: https://archive.ph/THcDL)
- Barb's birthday
- Jail Letter - 3 October 2021
- Jail Letter - 4 October 2021
- Jail Letter - 21 October 2021
- Jail Letter - 25 October 2021 (Kengle)
- Jail Letter - 25 October 2021 (Virginia fan)
- 2021 Jail Call
- Jail Letter - 30 October 2021