Headscale began as a learning project to work out “what was needed” to re-implement a Tailscale control server and unexpectedly exploded in popularity in the self-hosted and open source community as a home-labbers alternative to Tailscale.

Headscale has a vibrant community, about 6000 members in our Discord community and our Github repo has more stars than Tailscale’s open source client, but who's counting.

Three years ago I was hired as a member of technical staff at Tailscale, spending half of my time contributing and driving Headscale, ensuring the future of the project.

Headscale is a clone of Tailscale’s closed-source SaaS control plane, and it would be easy to consider it a competitor. Tailscale supporting Headscale this way is an unusual arrangement and sometimes raises eyebrows with "the internet".

It turns out that letting Headscale be autonomous and trusting it to run its own community complements Tailscale in a variety of ways. It helps people stay in the ecosystem. Homelabbers and self-hosted will use it at home, but bring Tailscale to work. Sometimes it even solves problems Tailscale can not.

Of course, it has not only been smooth sailing, and being a paid contributor has caused a lot of skepticism with some users fearing an “embrace, extend, extinguish” strategy, fueling conspiracy theories about our roadmap.

In this talk, I will share how the projects exist in symbiosis, the challenges of being a paid contributor, and how the stability of a corporate payroll has enabled Headscale to reach its current scale.