> So I can't just make a conditional in my config to go through TS instead of local network based on that
Tailscale can do hairpinning, so you may find you don't need a conditional config.
Thanks I'll look into that.
Though part of my gripe is just not having this in general. I can want to work on a certain machine I don't open and if I'm on an internal network but if external I want to do a proxy jump. The ssid is the most obvious and consistent way to determine this, at least to me. Anyone got another idea?
One big issue is Apple, who doesn't seem to respect DNS and VPNs, especially local network access... the other aspect is that it makes some ssh automation annoying because they will change things, such as getting the name of the current ssid (wtf?!). So I can't just make a conditional in my config to go through TS instead of local network based on that