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I have been trying to configure my pfSense router to allow me to connect remotely to my development VM without having to run a remote desktop connection to my office computer. Keep in mind, I am a software developer, not a network engineer.

First, I tried setting up OpenVPN, failed miserably after trying 5 different tutorials. From what I see it seems to be an issue with my pfSense since I'm not even able to update pfSense in itself due to a broken database in its package manager, but I'm not about to reinstall it since I'd have no idea how to set it up again.

I tried Logmein Hamachi as a VPN, which still didn't work, and lastly I tried installing OpenVPN in the development machine which, well, lo and behold, still didn't work.

On the development machine I need to be able to access port 80 (http), port 443 (ssl), port 21 (ftp), port 22 (ssh and sftp), port 3306 (mysql) and port 3745 (jenkins instance), I tried using NAT port forwarding but so far I've only been able to get pfSense to route traffic to a single machine, that being the production VM.

I tried using DNS forwarding, which just ends up resolving back to the production machine. Lastly, I tried removing all NAT rules to test if it was a misconfiguration on my DNS forwarding set up, but that's when I realized that it was still the rules taking effect, and that my DNS forwarding hadn't actually made a dent.

I do have other services like Samba which I'd love to be able to access but I have no idea how to get it to work. Any help would be heavily appreciated, even just a lead so that I know where to start.

This is a makeshift diagram of my network:

- comcast Router (OPT1)
- pfSense Router (public ip/WAN, everything under this is LAN)
    - office computers
    - proxmox
        - dev (0.0.0.1)
        - prod (0.0.0.2)

I made two A records (dev and prod) on my DNS provider (Cloudflare) for the domain I am using and I am pointing both of them to the only IP address we have available.

Thank you!

1 Answer 1

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I'm going to close the question because I was able to found a solution. It was not the way I had originally attempted to do it but it worked nonetheless. Instead of setting up the OpenVPN server on pfSense, I set it up on dev and then forwarded 1194. I was able to get Samba and everything else working.

Putting up this answer just for closure.

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