While this is great, especially for smaller self-hosters, as a setup gets more and more dependent on Tailscale, one should think about self-hosting Headscale, and therefore not being over-reliant on services not offered by it. I’m in that boat and I haven’t done the Headscale migration yet.

What is it about Tailscale that is giving you heartburn? I am over reliant on my ISP. Without them, selfhosting would be rather bland.

Ownership, size and profit growth strategy. My ISP is a massively profitable poorly regulated oligopoly. The deal there is clear - they’re already charging as much as the market can afford. They aren’t providing a free service today that they’ll have to monetize down the line to compensate for the time operating on VC funding. Tailscale, awesome as it is today, is in my view guaranteed to enshittify over time as they start getting pressed to grow profit. That’s not too much of a problem for me since the clients I use are open source and there’s an alternative open source server. If I used features unavailable in Headscale or were in over my head and unable to self-host Headscale, I might be in a bad time some time down the line.

Would it make you feel better if you paid Tailscale for one of their plans? It’s not like they are just giving away their whole enterprise. It’s fairly trivial for them to give free services, kind of like Cloudflare, Oracle, et al. Reading a bit reveals:

• Tailscale’s estimated annual revenue is currently $45.2M per year.
• Tailscale’s estimated revenue per employee is $230,489
• Tailscale’s total funding is $277M.
• Tailscale’s current valuation is $1.5B. (April 2025)
• Tailscale has 196 Employees.
• Tailscale grew their employee count by 23% last year.

That seems pretty profitable. Enshitification happens. It’s been going on since I was born. If it’s free on the internet, and later it becomes a paid service, then I just find something else that fits. Or pony up the cheapest plan they have, which currently is their Personal Plus @ $5 USD per month. I don’t mind paying for a good service and $5 USD is burger from McDonalds. Extremely well under what most people put into a hobby. Will prices increase? Maybe…everything goes up. Rarely do services and utilities go down in price. When the price points are no longer justifiable, again, I look for something else that fits.

There’s also Netbird, worth checking out.