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Tailscale First Impressions

Tailscale is a VPN for the rest of us:

A frustratingly simple VPN

Tailscale lets you easily manage access to private resources, quickly SSH into devices on your network, and work securely from anywhere in the world.

Oddly, while I probably could have put Tailscale to gainful use for quite some time, instead I just admired the technical depth of their blog posts. There’s been a lot of hype, criticism, discussion, etc. but the product seems to be a bit of a hit.

With a few spare cycles I finally decided to bite the bullet and give Tailscale a shot. In the last 24 hours, I’ve installed it on six machines, a mix of Linux, macOS, and iOS. Three are desktops/servers in my home, one’s a relatively stationary laptop, another’s a cloud node, and the last is an iPad. All easy, peasy 5-10 minute installs. The UX is to die for.

Haven’t attempted to use while away from homebase which is the next round of testing. So far, so good.

Once upon a time I noodled around with ZeroTier, which still seems to be chugging along. At that moment, the UX for ZeroTier was nowhere as smooth as Tailscale now, especially the outsourced identity management. I expect ZeroTier has sanded off a lot of the rough edges. The Tailscale folks even consider ZeroTier an admirable competitor.

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