This seems like an odd take. I remember when a large portion of the people I'd speak with online were very pro 2a while also being countercultural. There was a strong individual liberties/responsibilities, anti-government, pro-decentralization and devolution of power, and dare I say libertarian streak. This isn't an attitude I'd associate with the modern definition of progressive.

The big tech era certainly diluted a lot of that but I don't think it ever went away. I haven't seen a huge resurgence in this either so it seems strange to believe that tech is becoming less progressive. From my vantage it is still very far away from where it was in the 80s and 90s. I can agree that it has become much, much less countercultural since it's basically 100% mainstream opinion now.

You're not wrong. We're talking about different eras--and it sounds like you may have been around a bit longer. The mostly libertarian/individualistic (I would dare say _left libertarian_, who seem now to be pretty much politically extinct) era was notable to me in the late 90s through about the mid-aughts. This transitioned into a more progressive culture somewhere in the 05-08 era -- and its rise and fall pretty well overlapped with Twitter's, as best I can tell.

I can't directly speak to The Culture Of The Internet before about '97.