OpenVPN Remote Access - Should I Be Able to Ping...?

  • My OpenVPN client gives me the green light at my remote Windows 10 computer, but Windows Remote Desktop can't get to my computer inside our office MS Active Directory domain. The OpenVPN Client-side log shows that the tunnel is connected, which I set up as ans issues me an IP of I cannot get to my office domain subnet, which is set up in the pfSense Server Certificate as From this old novice, I would appreciate you sharing any ideas that you might have, whether obvious or not.

  • A couple of things to check:

    1. Do you have appropriate firewall rules on pfSense to allow the vpn traffic thru? By default, all incoming vpn traffic will be blocked.

    2. If you did #1, you might have to allow RDP connections on your Windows firewall.

    Firewall rule logging and packet capture will help you determine if the traffic is getting to pfSense and being blocked. Once you're confident that the traffic is passing thru pfSense then you need to investigate the Windows firewall situation.

  • I'll check the pfSense firewall rules. I used the Wizards to set up the protocols. Our firewall/VPN router had been running on pfSense 2.3.2 since 2016, but we upgraded to Windows Server 2019 and were informed that one of the protocols was now considered unsecure. The person who set the router up has moved to another city, so while running an engineering practice I'm spending my off-hours dabbling in IT issues that I haven't messed with for ~25 years. I'm now running to pfSense 2.4.5 via incremental upgrades from 2.3.2 - no problem with the upgrades from what I can tell. I'll also check the Windows Server firewall to see if RDP connections are allowed. Thanks for advise.

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