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Interestingly (I just found this out) Android permits 1 VPN connection per user profile.
So I run a VPN in my regular profile, and found my work profile wasn't using it. So I installed Tailscale there, and it works only in the work profile, while my regular VPN only works in my main profile.
If always assumed VPN config was a system-wide thing.
I remember figuring this out when I realized my vpn wasn't connecting while I was inside of my secure folder, which acts like it's own user profile