Hamachi was amazing, one of the best, most focused apps I've ever used. We were kids but it was still easy to use. Then they were bought by LogMeIn and was killed unceremoniously.

Also, it's old but not 90s old: https://swapped.cc/#!/hamachi released in 2004 actually.

The Hamachi UI and UX were great. I was very sad when it got bloated and then killed like a beached whale. I just looked and I guess it lives on as a whalezombie at https://vpn.net/.

This is ZeroTier territory. Not as polished as Tailscale, but provides L2 like Himachi and has been bulletproof for years already.

I remember XBConnect and GameSpy for playing Xbox Halo 1 over the internet. I think a couple were invented for every big game or console before 2010 or so.

Tailscale doesn't really address connecting to strangers, though.

Yes, XBConnect! Nevermind that you threw a grenade in Halo a whole 2 seconds after you pressed the button, you were playing with your friends! Good times.

I completely forgot about Hamachi. Remember using this as a teenager for creating private xbox lobbies over the internet

Hamachi was the OG user friendly VPN.

Not identical but in the 90s to play Windows games that only had a LAN mode over the Internet, we were using Kali in the 90s: https://en.wikipedia.org/wiki/Kali_(software)

This allowed us to play Warcraft II with random strangers: RTS games over the Internet... Felt like the future!

So many good memories from Kali!