Tailscale + VPN

[easyusername1111]

So i have a jellyfin server running fine on my local network, and while i am out and about i access it through tailscale. If my Server pc has my VPN(Mulvad) is on tailscale cannot connect. im an absolute noob, any advice is helpful.

[TheDreadPirate]

I'm not aware of anyone running two VPNs simultaneously with any success. I think it is hypothetically possible, but would require significant expertise and a lot of configuration (routing tables, firewall rules, etc).

[easyusername1111]

Would caddy be a better route of I'm trying to leave my VPN on? Or is there a way to have one drive for my server one drive for downloads?

[bitmap]

I'm not aware of anyone running two VPNs simultaneously with any success.  I think it is hypothetically possible, but would require significant expertise and a lot of configuration (routing tables, firewall rules, etc).

Yeah, uh...I do this. It's not worth the hassle. It's called split tunneling and if you're a novice or even moderately competent, it's above your skill level (because it was above mine). I struggled my way through this with OpenWRT, OpenVPN, Private Internet Access, and a plugin that allowed for routing tables via LuCI. It took me weeks to get it functioning properly and the only reason I kept going was because it allowed me to watch hockey via the ESPN+ app when games were blacked out in my region.

I also run Wireguard for remote access to my internal network. To make it even more complex, I run a second instance of PIA for outgoing/incoming traffic for my (micro-)services. So I'm running three VPNs simultaneously. However, there's a catch. The one on my router that split tunnels my traffic, which is what you would be looking to do, is the only one not containerized. The other two run in Docker, which makes the whole situation a LOT easier to manage.