Deepness in the Sky is one of my favorite books of all time! Fire Upon the Deep is a serious let-down by comparison, but the wolves are a cool concept.

As I've gotten older I've realized that I have very little in common with Vinge philosophically. But he was a person who thought very deeply, and it shows.

(ok mild spoilers ahead) Really why! I enjoyed them both and I read Deepness in the Sky first. It was a bit of a shock about FTL for me but I kind of granted narrative license so he could explore the range of consequences there, like with FTLness being distributed over a field of sorts. But yeah the dogs were dope, their packs, the interaction of the technological bootstrapping with them. Yadda yadda. I can't say I am familiar with his philosophy either

Any essays or articles in particular you're thinking of in relation to his philosophy?

Vinge is a full-on anarcho-capitalist. This is most evident in the Realtime series, particularly The Ungoverned which is pretty much entirely about the Bad Statists vs the Good Libertarians with Nukes. But it's also fairly obvious in Deepness, and to a lesser extent in Fire.

Since we're talking about cyberpunk specifically here, the Vinge recommendation that needs to be at the top of that list is https://en.wikipedia.org/wiki/True_Names. As literary quality goes, it's not as good as his later works, but it's still written by a computer scientist who clearly understands and loves what he does - not just as technology, but also as culture - and it shows. Features ARPANET, VR cyberspace, and hackers ("warlocks") vs NSA.

"True names and the opening of the cyberspace frontier" is a very nice edition with essays (Tim May's is very good) plus the novella of True Names, worth checking out!

His Realtime series (The Peace War, Marooned in Realtime) is also pretty good, in terms of “what if”.