Perhaps attacking people in previously marginalized groups is punching down, but attacking HR DEI enforcers is definitely punching up.
Personally - I think Scott Adams is more than a little bit batshit insane, but I certainly don't think he's punching down in the strips presented here.
I transitioned at work, and I've tried really hard not to be this character. I asked people to use my new name and pronouns but never complained to HR if they didn't. I made an effort to be as friendly and hardworking as possible, so that my conservative coworkers wouldn't see me through the lens of the "culture wars" like this that they're fed. This kind of comic was the stereotype I faced.
It worked for me. I changed peoples' minds, got respect for being reliable no matter my looks, and eventually started passing so nobody remembers I'm trans anymore.
Exactly, so by presenting in a particular way, you were able to get people to use the pronouns you wanted. I think this is the key to why people find pronoun declaration so meaningless — pronouns are meant as a shortcut chosen by the speaker to refer to another person based on who that person appears to be. Making pronouns into a declaration breaks a fundamental piece of language functionality for very little gain.
Dilbert works by personifying roles. It doesn't do much in the way of role subtext.
Those policies aren't coming from the peers.
When people who are and have been marginalized, after centuries of fighting, finally get some of the establishment on their side, it doesn't suddenly become "punching up" to mock and satirize the efforts to get them the recognition, opportunity, and equity they deserve, even if said punches are, on the surface, aimed at individuals with positions of power.
I think to explore this further we'd need a clearer definition of "punching up".
I think that if you really wanted to make a workplace comic that skewers HR departments' often hamfisted attempts to promote diversity (which is often because they themselves don't really care about it, and have just been given a mandate), you need to center the people with the real issues, rather than the ones who are being mildly inconvenienced by it.
Have a trans employee complaining that HR is happy to jump down people's throats for accidental misgendering, but still hasn't actually processed their name change paperwork and informed IT, so the intranet is still deadnaming them.
Have an employee of color upset that they've plastered black, Hispanic, and Asian people all over the company's website, but he's just gotten passed up for promotion for the third time to a white guy who worked there less than a year and who does nothing but kibitz all day.
Have a Jewish employee angry that the company has branded kippahs that they give out alongside their other swag, but won't give the Jewish High Holidays off as paid holidays.
In general, play up the empty tokenism, while emphasizing what's really important. (Making it also funny is left as an exercise for the reader; I don't claim to be a comic.)