September is the ninth month of 2020. As of this month, the COVID-19 pandemic has spread throughout the United States for half a year. Chris dedicates most of the month answering questions from his True and Loyal Fanbase through Discord.
- 2 September - The two debt cases from January wrap up; Chris owes $2,773.56 to one of his creditors and $905.36 to the other.
- 2 September - In a message to a Watchman, Chris discusses his debt hearing, Transformers toys, and the Dimensional Merge.
- 4 September - Chris has Barbara record a video saying she's fine.
- 4 September - Chris records a reaction video to the fourth part of TF2 Analysis's Red Vs Blue brony cartoon.
- 8 September - Chris answers more Q&A questions through Discord.
- 9 September - Chris continues to answer the questions.
- 11 September - Chris responds to even more Q&As.
- 15 September - Chris answers his seventh Q&A on Discord.
- 16 September The first of the released The Journey to the Merge Discord caps takes place.
- 24 September - Chris responds to more questions on Discord.
- 30 September - Chris releases a video in which his mother addresses his half-brother Cole.
- Bonus short update from Barb 09/04/2020
- Watching TF2 Analysis Anarchy Red Vs Blue Part 4, plus a few thoughts.
- To Cole Smithey, from Barb, and Sonichu (Prime)