Selfhosted
A place to share alternatives to popular online services that can be self-hosted without giving up privacy or locking you into a service you don't control.
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Cloudflare Tunnels work great and are really easy to setup. Plus you are not exposing you machine completely to the outside, as the cloudflared service/container „calls out“, and Cloudflare is your reverse proxy. Downside is, you’re binding yourself to one of the US hyperscalers.
Pangolin uses the same principle, but is a bit more challenging to setup. Plus you need some kind of cloud server to make it work.
As you already have a VPN active at all times (at least it sounds like that), a VPN home seems out of the picture.
Unless you have a dedicated firewall at home, maybe reconsider the reverse proxy route. Personally would not feel comfortable with exposing a machine at home to the internet in full without a handle on what it can do or how it may be reached.
Expand on that, if you would. I run local VPN and everything else through Cloudflare. In fact the VPN DNS is Cloudflare as well as the stand alone pFsense firewall. Perhaps I am misunderstanding, which is likely since I'm all drugged up trying to pass a kidney stone.
Well, not every system can handle or support multiple VPN connections with different providers, or the VPNs could interfere with each other. E.g. when using Tailscale you can not use another WireGuard based VPN according to their FAQs.
Also, it adds complexity to the stack and system as a whole on the client side. That is all fine and dandy as long as it works, but quickly a pain in the butt once you have to debug something.
Wireguard + OpenVPN works well for me.
OpenVPN fully supports multiple simultaneous connections. But Wireguard is such a pain in the ass with this. But Wireguard dgaf about OpenVPN connections.
Anecdotally, if I turn off the Advanced killswitch and The VPN killswitch of my main VPN, I can actually bring up Tailscale. But you are right, it does add complexity. Basically I use Tailscale on the server and pFsense firewall as an overlay VPN. It's also handy if you lock yourself out of the server. A 'backdoor' of sorts.