June was the sixth month of 2021. 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.
The Watchmen, a white knight group, broke up following internal conflicts among its members.
- 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. It would later be revealed that this was a result of manipulation by The WCT, a ween working with Isabella Loretta Janke who had held a bizarre obsession with Stair himself since at least July 2018.
- 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.
- 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.
- 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 - According to Chris himself, Chris begins to engage in incest with his mother around this time - news of this would not break until July 2021.
- 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.
- Sean Walker / @Psychic Espeon / Lainchu / WCT / WildCat / Neko (etc.) - Self-described "Final Protagonist of Christory", spree-killer fanboy, connected to Bellagate
- The WCT Page on a wiki created by Sean himself
- Incest Discussion