[password4321]

The question is: how long will Headscale be supported in the official clients - how long will the incentives of Tailscale's VC's align with the freeloaders?

The official clients (most valuable: the polished mobile apps easily installed from the default app stores) are one auto-update away from cutting ties when push comes to shove, the same as all commercial VPNs with a free tier.

[jmprspret]

The clients are the open source part of Tailscale. They can be forked and built by someone else if required.

However I do not think Tailscale is going to remove the custom control URL feature from their mobile clients. For one, I think there are legitimate "Tailscale Enterprise" use-cases for the custom login server.

Additionally, I have heard that Tailscale has been supportive of the Headscale project, providing assistance to the devs.

Further, Tailscale seems fairly committed to keeping their clients open sourced, and engaging in the developer community. Of course as you can say this can change at any time.

[figassis]

I think clients are the least to worry about. They can be built by someone else if the need arises.