September was the ninth month of 2016. Chris continued in this month to earn money by posting paid videos. He attended the Cville Pride Festival, the annual Charlottesville LGBTQ pride festival, for the third year in a row. He got a new cat called Sorbet. He ramped up his criticisms of presidential candidate Donald Trump, a trend that would become more acute in the coming months. Otherwise, Chris continued to dick around with his toys and occasionally make posts on Facebook.
- 4 September - More emails from the 2009-2012 era of Christory are leaked.
- 6 September - Chris posts about his opinions of Donald Trump using Transformers toys.
- 6 September - Chris makes a paid video birthday greeting for fan Alex.
- 7 September - On Facebook, Chris reminsces about better times when he was more creative and less bothered by trolls.
- 7 September - Chris makes a "Paid Message to the Trolls" in which he calls out Kiwi Farms and mocks Donald Trump.
- 8 September - YouTube member "Lil E" uploads an interview with Chris.
- 10 September - Chris posts a word salad on Germany's Autobahn, the Transformers franchise, and his wish that Hitler hadn't died in 1945.
- 12 September - Chris is photographed shopping at Toys R Us.
- 14 September - Greene County's court rules that Barb owes $15,906.99, from unpaid debt, to Capital One Bank.
- 17 September - Chris attends Cville Pride with Vinyl, a toy doll from the Equestria Girls show.
- 17 September - Chris has questions about Transformers for his Facebook friends.
- 18 September - Chris reminds Facebook that his old TrollBusters campaign is still relevant.
- 19 September - Chris announces that he has a new pet cat, Sorbet, and begs for money.
- 22 September - On Facebook, Chris comments about a piece of My Little Pony merchandise.
- 24 September - Chris registers to vote.
- 25 September - Chris explains that he won't vote for Trump because of a satirical depiction of him from The Simpsons, and because Trump "spelled backwards is 'Pmurt,' which rhymes with 'Hurt,' and he would badly 'Pmurt' this country in office."
- 25 September - Chris posts three more cat photos and invites his audience to play a guessing game.
- 26 September - Chris discusses the new Equestria Girls movie on Facebook.
- 27 September - Chris offers his analysis of the political debate between Hillary Clinton and Donald Trump on Facebook.
- 27 September - Chris uploads a paid request in which he rambles about a character from Steven Universe.
- 27 September - Chris posts a political commentary) which consists of him sitting alone in his room and playing with his toys like a child. He also uses the term "we" to refer to himself and a doll he made in effigy of himself.
- 27 September - Chris posts a brief addendum to the above anti-Pmurt video.
- 29 September - On Facebook, Chris tells Hasbro to make more Transformers toys.
- 29 September - Chris uploads a brief paid shout-out to two fans.