I’ve noticed that there’s a lot of transphobia within homestuck and post canon.
Within the bounds of the original comic run, one thing that I notice immediately is March Eridan. They decided to present the racist eugenicist as a femboy. Femboys for those not familiar are people who appropriate the aesthetics of transfeminity in an easily palatable way for a bigoted audience.
There is the greater issue of post canon Jade. Let me start off by saying within the epilogue Hussie decided to give Jade a dog penis. This is shown to immediately affect her behavior, a transphobic thing on its face pointing towards ideas of bio essentialism. The behavior changes made are transmisogynistic, especially given how much they diverge from her original character. She becomes aggressive both sexually and physically, shown to attack and act predatory to gay men. Her hypersexuality is also playing to a bigoted idea of a trans woman. That’s not to mention the fact that polyamory is shown in two instances, and both are clearly just cheating.
This issue continues in homestuck two. Jade is routinely called a bad mother, and her cis mother is forced to step in. She’s shown as a cheater who wants a child as an object to prove she can be a mother. The worst example is that they decided to depict her as a soyjak, a bigoted form of meme meant to show people right wing users don’t like as “soy boys.” This is often used to make trans suicide jokes as well. Not only is she shown as this, she’s given facial hair as well.
Then there’s the issue of June. She was introduced in one slide in beyond canon. Then subsequently in the same update they decided to call John a pedophile. Now finally, I move on to the harder to prove. Roxy in the original homestuck comic is depicted as transfem and was commonly seen as such in the fandom at the time. This is mostly rooted in stereotypes, and the fact her name plate is chromosomal. However, it was the popular headcanon at the time.
What the epilogues decided to do was make sure every character was confirmed as cis by forcing them to have children in order to erase trans interpretations. Then, Roxy who was broadly seen as transfem was made into a trans man. It’s hard to see this as anything but spite for the fans. If that is too tenuous, which I understand. There’s the fact that candy Roxy detransition and frames being trans as a choice chose not to make because she had a baby and her gender troubles were fixed.
Finally there’s psycholonials. The gender pyramid refers to nonbinary identity as clown like and then states caring about your gender is equally stupid. Caring about your gender is described as horse gender and ascribed to Rowling a known transphobe. It’s clear from this that Hussie doesn’t respect trans people.
Each individual aspect might not seem compelling but when taken in connection, it paints a clear picture.