THIS

While I would make the modification to use Android’s Private Space instead of a work profile (or Shelter instead of Insular), this was such an obvious solution, and I feel stupid for not seeing it. I might use Wireguard instead of Tailscale, I don’t know yet, but thank you! Consider yourself an outside the box thinker!

We all got hung up on trying to fix Proton, when Android was the issue here!

Thank you for this!

Is OPNsense like dd-wrt or OpenWrt?

The thing is (and this is by no means a knock on you) if you are doing pen testing then you definitely need to increase your knowledge on networking.

I have background in Wi-Fi hacking and LAN attacks, and I understand the structure of networking (LAN, WAN, layers of the internet, DNS, CAs, etc.). My head starts to hurt when RADIUS is involved, ad hoc networking (which I understand the concepts of, just not how it works. I want to learn this first), mDNS, and other complicated topics. I’m trying to push past those mental roadblocks and learn as best I can, but it’s a tricky topic!

https://wiki.freeradius.org/

There’s something to check out just to get some concepts. You can do plenty of things to harden your security that could give you the comfort you need without defaulting to encrypted connections over LAN.

Thank you! I’ll definitely check this out. You’ve been a huge help!

Since I always have ProtonVPN enabled, and Android devices only have one VPN slot enabled, I cannot use something such as Tailscale for encryption.

This is fair, and does solve the problem. I didn’t explicitly state that I needed it to be convenient, so you’re right. Having one network that is LAN only and switching to it to use Jellyfin, and having a second network that is WAN only and using ProtonVPN there would probably be the most secure setup. Unfortunately, it still doesn’t solve the issue of encryption in transit over the LAN, but that might be fixable with Tailscale. The LAN could even be ethernet-only, to mitigate wireless attacks.

That makes me wonder if there’s a way I could simply plug an ethernet cord from my phone to the airgapped Pi and use it that way. Is that possible? Surely it is. Could ProtonVPN be used on the phone even while the phone is connected physically to the Pi?

No, it can run along anything, as long as you don’t conflict the IP space assigned to a VPN.

I tried Tailscale on Android, and it isn’t working because it requires the active VPN slot occupied by ProtonVPN.

Okay, so you might be unfamiliar with networking

I’m familiar with some parts of networking, but selfhosted VPNs are something I am unfamiliar with, so thank you for helping me out!

No need to use Tailscale if you’re just using your Wi-Fi or Ethernet.

I want it to be encrypted during transit, even if it is over the LAN.

Tailscale/Headscale creates it’s own VPN network which will need its own IP space.

This is what I was afraid of, because this means it probably can’t run alongside ProtonVPN, since it would fill up the VPN slot on Android, right?

If so, it means we’ve come full circle. Unless there is a way to use Tailscale alongside ProtonVPN or a way to get Jellyfin clients to trust self-signed certificates, I don’t see any other option than buying a domain and exposing the server to the internet. Am I missing something?

I know. It’s very unfortunate, but I understand why.

You want to use it only locally (on your home), but it can’t be a local-only instance.

By “local-only” I meant on-device

You want to e2ee everything, but fail to mention why.

Privacy and security.

There is no reason to do that on your own network.

Networks are not a trusted party in any capacity.

I do not know why you want to use a VPN and what you want to do with it. Where do you want to connect to?

A VPN such as ProtonVPN or Mullvad VPN are used to displace trust from your ISP into your VPN provider and obscure your IP address while web browsing (among other benefits that I don’t utilize).

What is the attack vector you’re worried about? Are there malicious entities on your network?

These are good questions but not ones I can answer briefly.

Alright, I’m slowly learning, bare with me here:

• ProtonVPN is always-on and blocks connections without VPN
• Jellyfin and Headscale are hosted on the Pi (or does Headscale need its own server?)
• Tailscale and a Jellyfin client are installed on the phone

Then:

• Will that will run fully on the LAN?
• Will it be encrypted during transit?
• Does ProtonVPN need to allow LAN connections?

So:

• ProtonVPN is installed on my Android phone
• Android has Always-on VPN enabled
• Android has Block connections without VPN enabled
• Host Jellyfin on my Raspberry Pi 5
• Install Headscale on my Raspberry Pi 5
• Install Headscale on my Android phone
• Install a Jellyfin client on my Android phone
• Configure everything

And that will work? It will be encrypted during transit? And only run on the LAN? Does ProtonVPN need to allow LAN connections (I assume it does)?

Does Headscale conflict with ProtonVPN/Mullvad VPN (i.e. can I use those alongside Headscale)? Android has a limited number of VPN slots, so that’s why I ask.

Run in at home and get Tailscale setup with a Headscale server, or just use Tailscale straight out of you want. That’s the simplest.

I have no idea how to do this. Do you have any resources? Does it cost a subscription fee?

A better option would be getting an OpenWRT router

This is what I have planned. OpenWrt Two my beloved

You’ll have many different options for decentralized and NAT traversing VPNs with this option. GL.Inet Flint is a great choice.

I also don’t know how to do this. Resources are much appreciated :)