Can't VPN in to Port 1194 When Router Is Using VPN

I am trying use OpenVPN to connect to my home network when I am not at home. If the VPN is active on the router I cannot connect, if the VPN is turned off I can connect as expected.

I am using a custom subdomain on DuckDNS to connect to PIVPN and my PiHole when I am not on my home network. If the VPN is active on router the connection never completes, if I disable the VPN on the router I can connect. I am trying to use my PiHole and obfuscate my IP when I am not on my network.

I am aware that I am trying to VPN to a second VPN.

Using my VPN provider alone on my phone does not solve my problem, because it removes the blocking my PiHole provides. Disabling the VPN on the router reveals my true IP, and is not the solution I’m looking for. I am trying to have the benefit of the PiHole with the VPN company obfuscating my IP whether I’m home or not.

If it helps I have an unused GL-AR750 I can put on my network.

Bumping this in case it was missed over the weekend

Want to make clear, you connect the router via VPN to your home PiVPN server.

And it connects.

And they you need to use your PiHole?

Seems that you have connected to you PiVPN?

The Router has a DD-WRT file for Proton VPN, when the router is connected to Proton VPN I can’t connect to PIVPN on Port 1194, when it’s not connected to Proton VPN I can connect to PIVPN on Port 1194.

What I’m trying to achieve is this

Phone > Router > PIVPN > PiHole > Proton VPN

It is a little bit clear now. But still confuses.

You said router is connected to ProtonVPN and you want to connect to PiVPN on your phone.

So it seem like this

Phone > Router > Proton VPN > PiVPN > PiHole

But seems your setup has problems.

  • All of your data will go through your PiVPN finally and the website will think you are using Internet at home.
  • Your carrier will know you are using ProtonVPN, not using your home vpn. But does this matter if they know you are using your home VPN? If does not matter, just connect the router to your home VPN.

You are focussing on ways to try and simplify what I’m doing, has it ever occurred to you that I have put a lot of thought into this and I’m doing things this way on purpose?

I am extremely concerned about my privacy, and blocking advertising and marketing companies from tracking me is a top level concern. I want to block the tracking across my entire network, and the most efficient way to do this is with a PiHole. Additionally I want to obfuscate my IP and location, so I use Proton VPN to do this.

I want to use both my PiHole and Proton VPN when I’m not on my home network. The best way to do this is with PiVPN on the same Raspberry Pi running the PiHole.

Using this strategy it’s entirely possible to prevent your location from being tracked using your cell phone. I know you don’t believe me and think that’s impossible, I can assure it is possible. I’ve been doing it since November of 2019 and have only connected to cell phone towers four times since then, the last time was in April. Here’s an overview of how I do it:

I know it seems like I’m adding extra steps and taking the long way to do this, but I have an very specific path I’m trying to use, and simplifying the process is going to remove a mission critical component I put there for a reason.