On both ends.
Software developers hate boring software for pragmatic HR-driven career reasons and because devs are apes and apes are faddish and like the shiny new thing.
And commercial hegemony tends to go to the companies that slap something together with duct tape and bubble gum and rush it out the door.
So you get clusterfucks like Unix winning out against elegantly designed Lisp systems, and clusterfucks like Linux winning out against elegantly designed Unix systems, and clusterfucks like Docker and microservices and whatever other "innovations" "winning out" over elegantly design Linux package management and normal webservers and whatnot.
At some point someone important will figure out that no software should ever need to be updated for any reason ever, and a software update should carry the same stigma as...I don't know...adultery once carried. Or an oil spill. Or cooking the books. Whatever.
But then also it's important to be realistic. If anyone ever goes back and fixes any of this, well, a whole lot of very smart people are going to go unemployed.
Speaking of which...