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Is this because HS hasn't implemented it yet (which is on the community), or because Tailscale does something to prevent them from working specifically?

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Is it on the community, when TS have said that they won't open source their control plane because HS is good enough / easier to run?

it's a proposed and planned feature by the looks of it :

https://github.com/juanfont/headscale/issues/1651

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