White hats? If white hats were building actively guided systems capable of that sort of range, you'd be seeing miniature computer boards running Linux, Squid and Tor relays launched into stable orbits that crossed nations with restricted network access. We don't.
I don't usually comment in the gun threads, since it's not my hobby, and usually someone would have noticed this remark and answered it by now, but we're 400 posts and counting into the thread and still no one has, so I will.
We do. Ham radio enthusiasts (who have a not-inconsiderable intersection with gun enthusiasts) have put multiple relay satellites in orbit, and you could call them miniature. They're certainly reasonably small compared to normal commercial satellites, even if they're mostly not CubeSats. Some of them are intentionally put into inclined orbits, so they cover more of the Earth's surface, including crossing nations with restricted network access. No, they don't build actively guided systems of their own to do it. They launch as secondary payloads. They operate mainly as store-and-forward systems. Email, basically, or Internet newsgroups.
I don't recognize your reference to neocon stupidity, but I concur that it was stupid. There are existing orbital solutions to the problem of rampant censorship.