June was the sixth month of 2021. In a disturbing turn of events, this was the month in which Chris began engaging in incest with his mother. This went under the radar for over a month, and only became known to the public by late July.
Chris uploaded a few videos this month, most notably one in which he wishes a happy birthday to a Devin. Aside from this, Chris made miscellaneous social media posts about Tarot cards, and claimed that the organizers behind the TooManyGames convention conspired with the trolls.
- 1 June - Chris briefly roleplays as his younger pre-name change self on Twitter in order to address any issues regarding the Warhol / Chris Chan book.
- 3 June - Chris starts posting daily photos of various Tarot cards on Twitter.
- 4 June - A fan takes a photo with Chris at a Barnes and Noble bookstore.
- 10 June - Chris discusses his Top 5 list of people who made the most negative impacts on his life. The list includes the Idea Guys, Jacob Sockness, Michael Snyder, BlueSpike, and the staff of Nathanael Greene Elementary School.
- 13 June - The owner of the Charlottesville Fashion Square Mall files for Chapter 11 bankruptcy. 
- 15 June - Chris makes a comment about mass shooter Andrew Blaze on Youtube; he treats Blaze as an imaginary friend and says that he, Blaze, and Andy Warhol are all interdimensionally awakened individuals.
- 19 June - Chris uploads an audio clip of himself laughing at an OneyPlays joke on Twitter.
- 19 June - Chris records a video of himself sending a birthday message to one "Devin", and then briefly tours around his house whilst scat-rapping.
- 19 June - Chris tweets a video of him baby-talking to and playing with his cat Sylvia.
- 19 June - Toffee Rosechu, a fantasy enabler of Chris's, tweets about a family tragedy while expressing skepticism over his belief system. Chris DMs her to discuss further.
- 20 June - A video of Chris talking about the Binding of Isaac is released.
- 22 June - Chris breaks his 193-day long streak of not begging with a Twitter rant about money, saying he is open to donations for a new car.
- 24 June - Chris makes a few tweets on Twitter regarding conventions, claiming that the TooManyGames incident was supposedly a trap by the trolls, and that he had attended several local rock and stamp conventions.
- 25 June - Chris makes another set of tweets regarding TooManyGames, claiming that the convention staff and organizers conspired with the trolls to set up a trap.
- 25 June - The WCT makes a call Chris to discuss his suspicion that fellow Watchman Naught had doxed him. WCT encourages Chris to leave their Discord group and join his own.
- 25 June - Chris joins The Knights of CWC, a splinter Discord group of Watchmen set up by The WCT.
- 26 June - Chris leaves The Place, the previous Discord group of the Watchmen, cutting ties with Naught, Kyle and MKR.
- 26 June - Null announces that Chris is planning to attend Everfree Northwest, a My Little Pony convention held in Seattle, WA, on 13 August. He mentions vetoing Chris's plan to drive there and recommended taking a flight, and says he will help Chris with financial arrangements.
- 27 June - Chris begins engaging in incest with his mother.
- 29 June - A series of tweets by MKRNightVee hints at the breakup of the Watchmen group.
- 29 June - An anonymous fan on 4chan's /pol/ board photographs themself going to Chris's house.
- 30 June - The full uncut version of the Taser Discussion is released, revealing the fact that in the original audio, it was a Watchman member who jokingly floated the idea of Chris tasing himself, after which Chris volunteered himself, and a Praetor member told him it was a bad idea.
- The Knights of CWC chats (June 2021)#Chris Enters
- Incest call#Transcript
- WCT DMs#New sweetheart