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I have an OpenVPN server running on a VPS. When I connect to the VPN using the redirect-gateway option to route all traffic from the client through the VPN, Skype loses its connection. As soon as I disconnect from the VPN, Skype goes back to being connected as normal. I've tried closing and restarting Skype after enabling the VPN and again after disabling the VPN, and I've also tried closing Skype before connecting to the VPN, then connecting, then starting Skype up once the VPN is connected. None of it makes a difference; Skype works if and only if I'm not connected to the VPN.

This problem occurs on multiple computers, using both Linux and Windows 8.1. All the computers use the same OpenVPN client configuration file so this doesn't rule out an error in the client config.

As far as I can tell, Skype is the only program affected. I can browse the web and check email just fine whether I'm connected to the VPN or not. Unfortunately Skype produces no debugging output, so I can't tell exactly why it's not connecting. I've been watching the network behavior with Wireshark and netstat, and I see some RST packets coming in from the hosts Skype is connected to, but that doesn't get me much closer to a solution since I don't know why they're coming or how to stop them, or even if they have anything to do with the problem I'm having.

I would like to get Skype working with its traffic routed through the VPN. I'm not sure whether it's the client's or server's configuration that needs to be changed to make it happen. Any idea how to fix this, or at least what information to look for to identify what's wrong?

Here's the routing table from ip route on one of my Linux clients without the VPN connected:

default via 192.168.1.1 dev enp1s0  proto static  metric 1024 
127.0.0.0/8 dev lo  scope host 
127.0.0.0/8 via 127.0.0.1 dev lo 
192.168.1.0/24 dev enp1s0  proto kernel  scope link  src 192.168.1.5 

and with it:

default via 10.100.0.13 dev tun0  proto static  metric 1024 
10.100.0.1 via 10.100.0.13 dev tun0  proto static  metric 1024 
10.100.0.13 dev tun0  proto kernel  scope link  src 10.100.0.14 
69.x.x.x via 192.168.1.1 dev enp1s0  proto static  metric 1 
127.0.0.0/8 dev lo  scope host 
127.0.0.0/8 via 127.0.0.1 dev lo 
192.168.1.0/24 dev enp1s0  proto kernel  scope link  src 192.168.1.5 

I've partially anonymized my VPS address.

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  • I have not used skype for a while, does it still require you open a local port to receive incoming packets ?
    – dotvotdot
    Feb 17, 2016 at 11:43
  • It might. I'm not sure since I don't run a firewall on the Linux client, and I don't know if I would have to do something to manually open a port in Windows. Maybe I'll look into that.
    – David Z
    Feb 17, 2016 at 12:09
  • If it is possible open the port on your VPS and your VPN client, then forward packets to your VPN client on that port.
    – dotvotdot
    Feb 17, 2016 at 12:17

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