OpenVPN in a virtualized environment



  • How do you get OpenVPN working with a VPN provider when running pfSense in a Virtual environment? I currently have a working pfSense box but I've been experimenting installing pfSense on my Hyper-V server. I have it setup exactly as below and everything is working apart from being able to connect to my VPN provider (IPVanish).  The Interface is up but the gateway is offline and I'm assuming this is something to do with it being virtualized as the exact same config works fine on my physical pfSense box. I can't seem to find any info on this, could someone help point me in the right direction please. I should also add my WAN connection is via PPPoE.

    Thanks.




  • LAYER 8 Global Moderator

    looks like you got an IP from ipvanish, and just your gateway monitoring is not working..  What IP are you using for monitor in your gateway settings.

    I run a vpn connection to one of my vps via openvpn client setup on pfsense that is running as vm on esxi.. There would be nothing I could think of in vm setup other than maybe a double nat setup?  That could cause you problems.  But you hid your wan IP so I take it that is public in pfsense.



  • @johnpoz:

    looks like you got an IP from ipvanish, and just your gateway monitoring is not working..  What IP are you using for monitor in your gateway settings.

    I run a vpn connection to one of my vps via openvpn client setup on pfsense that is running as vm on esxi.. There would be nothing I could think of in vm setup other than maybe a double nat setup?  That could cause you problems.  But you hid your wan IP so I take it that is public in pfsense.

    I'm using a Huawei modem but I have it unlocked in bridge mode so double NAT shouldn't be my problem. My Gateway is setup as below, I have it set as Dynamic IP and I've not added anything in for the alternate monitoring IP.




  • It may possibly be that the default monitoring IP doesn't respond to ping requests. Try entering an alternate monitoring IP such as 8.8.8.8 (google DNS) and see whether that shows it as online.



  • Just tried that and still the same. The settings are exactly the same as my bare metal pfsense box, the only difference is this one is a VM. Can't figure out for the life of me what is causing it to not work.


  • LAYER 8 Global Moderator

    Who says its not working… You are clearly getting an IP from them...  So clearly the connection is up! Check what IP your monitoring..  Are you getting public from them or rfc1918?  Don't most vpn providers give you rfc1918 and nat it... I don't see how they could give out public IPs to all of their customers..  Not ipv4..



  • HI guys. I'm new here and have similar problem. I have win7 desktop that has 2 realtek Nics and i'm running vmware workstation on it that has pfsense vm on it as host.
    When i reset my cable modem my pfsense vm won't get comcast wan ip address or it will and then it will get dropped as soon as i access dashboard on lan. Most of the time i won't even get comcast ip in pfsense. It will be assigned to my desktop pc physical nic however so then i bridge physical nic with vmware nic1 but that don't help. Other options is NAT or host and neither works. I have 2 virtual adapters from vmware and 2 physical adapters. My setup looks like this



  • LAYER 8 Global Moderator

    Rango start you own thread - your problem is nothing like the OP problem at all…



  • Your setup is radically different than but I also have a pfsense VM on a Hyper V server and have no issues running openVPN on it. I use the virtual hyper-V adapters, etc.
    The issue is not on the Hyper-V or pfsense.

    As other have suggested it could be a NAT issue


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