OpenVPN MacOS Limited Connectivity
CNLiberal last edited by
I've got pfSense 2.4.4-p2 running on a Dell R210II. I've got OpenVPN Server configured. From Windows, the OpenVPN GUI is working as expected. From MacOS Mojave (Tunnelblick) and OpenVPN for Android, I'm having issues where some IPs on the server side are pingable, and others aren't. I've got my pfSense box as simply a firewall. I've got a L3 switch on the LAN side with OSPF enabled between the two devices. When connected to VPN, I can ping and access the pfSense device (10.0.14.1) and the L3 switch (10.0.14.2). I can't ping any device on the internal LAN (10.0.0.0/24). But I can ping and access a device (10.0.11.180) off a DMZ interface (10.0.11.0/24) of the pfSense firewall.
In MacOS I can see a route for the 10/20 network (that is the correct network statement which is entered in the OpenVPN Server config). Here's the output of netstat -nr on the Mac:
user@MacBook-Pro.local:~$netstat -rn Routing tables Internet: Destination Gateway Flags Refs Use Netif Expire default 10.0.0.1 UGSc 76 41 en0 10/24 link#5 UCS 3 0 en0 ! 10/20 10.0.15.1 UGSc 2 2 utun3 ... 10.0.15/24 10.0.15.2 UGSc 2 0 utun3 10.0.15.2 10.0.15.2 UH 1 0 utun3
I'm not sure why on Windows this is working fine, but on MacOS it's not. Also, I don't understand why on my Android devices it sometimes does and does not work. Very strange. Any help would be appreciated. Thanks!
Pretty much everyone who uses a Mac and wants OpenVPN to work buys a copy of Viscosity.
Probably a good time to run a 30-day trial.