OpenVPN Client on MacOS Catalina running on 2nd attempt

guille

Hi everybody,

I am experiencing a problem with the OpenVPN client in MacOS.

I have OpenVPN installed on a Synology NAS, running perfectly from Windows. But when I connect from a Mac with Catalina OS, the first connection is established, but I can't ping any computer on the target network.

If I disconnect VPN and reconnect after a few seconds, it works perfectly and I can connect to all resources on my Mac Mini server and ping all my LAN computers.

I've tried it with the OpenVPN client v3 for MacOS and also with Tunnelblick, and both programs have the same problem. First connection appears connected, but ping failing.

Once connected (on second attempt), the connection is 100% stable and I can work normally. Only the first connection fails, if I then disconnect and reconnect it always goes well, until I restart the computer, then the first connection fails again (login successful and appears connected, but I can't ping any computer on the LAN).

Any ideas?

Thanks in advance.

TinCanTech

All we know is what you told us .. tell us more.

guille

Solved!

The problem only occurs when the source and destination network addresses use the same range.

My laptop is connected to my home LAN with a 192.168.1.x address. The destination server is also on a LAN with 192.168.1.x address.

I fixed the problem by adding a line to the OVPN configuration file with a static route only to my Mac Mini Server located on the destination LAN.

route 192.168.1.XXX 255.255.255.255
(XXX=My Mac Mini IP address)

Now, my OpenVPN client (Tunnelblick or OpenVPN client v3) in my Macbook laptop, connects at first attempt to the destination network and can access to my office Mac Mini Server without problems.

Regards from Barcelona (Catalonia).

Pippin

That's not really the solution, please see here:
https://community.openvpn.net/openvpn/wiki/AvoidRoutingConflicts

guille

Thanks, Pippin, for your quick reply.

I understand that the best solution is to use different IP ranges at the source and destination, but the intention now is not to have to change the IP address of all the computers in the office, which are connected to a network with addresses of type 192.168.1.XXX (similar to those used by home networks).

In addition, I have no way to manage routes on the OpenVPN Server, as it is embedded in a Synology NAS device, with few configuration options.

Regards,

TinCanTech

guille wrote the intention now is not to have to change the IP address of all the computers in the office, which are connected to a network with addresses of type 192.168.1.XXX (similar to those used by home networks).

That's called a "notwork" .. individual networks must have unique IP addresses.

However, if your home devices only need access to the office then it should be ok.