OpenVPN / Tunnelblick – auto retry connection with credential error

How can I get OpenVPN on MacOS to auto-retry a connection with a credential error?

I’d like to run the connection on startup and keep it connected without user interaction. I expect a disconnection on the ISP’s side to happen every now & then.


I’m using tunnelblick to manage connections and keep the connection running.

When the client gets disconnected and tries to reconnect, the server often doesn’t realise the user was disconnected, and as it only allows one connection per user it gives a login failure.

This would be fine if tunnelblick auto-retried the connection, but it asks for confirmation instead. The client machine isn’t always physically accessible when this happens so it will stay disconnected until a user manually authorises the reconnection.

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  1. If you are saying the authorisation is from OSX then you have no choice but, if the authorisation is due to login to the VPN server, then all you need to do is open up the ovpn file that you are using and look for the statement, auth-user-pass in your file.

    Replace this with

    auth-user-pass ‘userid/password file’.

    Make sure userid/password file is pointing to the actual path of file that you will created. This will shall have only the following content:

    Well, you have to put real username and password to make it work. Maybe you can name the file as vpnprovider.passwd in your home folder.

    Do this for all the ovpns from the same provider that you will be using.

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