Keep that VPN Connected (MacOS)

I recently found myself regularly traveling, and I wanted to ensure that no matter when I opened my laptop, that my wifi connection would be secure. However, there’s no way using built-in OSX VPN client to connect on boot or wake-from-sleep, nor is there any way retry after the failure of your VPN connection. Good thing that Apple made AppleScript!

I have a personal VPN server running on a 5$/mo Digital Ocean server which is configured with this amazing script: https://github.com/hwdsl2/setup-ipsec-vpn. I’ve got my VPN configured in the MacOS Network settings as vpn-evan and I’ve got "all network traffic" going though it. That should keep me safe…

Create the Reconnection Script

Open Script Editor and paste in the following:

applescript

on idle
	tell application "System Events"
		tell current location of network preferences
			set VPNService to the service "vpn-evan" -- replace this with the name of your VPN connection
			if VPNService is not null then
				if current configuration of VPNService is not connected then
					beep
					beep
					beep
					connect VPNService
				end if
			end if
		end tell
	end tell
	-- in "idle" blocks, the number returned is how long to sleep until running again
	return 60
end idle

Let’s break dow this script:

When the application is idle
Find your VPN connection
If it’s disconnected, beep at us (so we know what’s happening), and then try to connect
Sleep for 60 seconds and check again

Be sure to replace "vpn-evan" above with the name of your VPN connection

So if this program is always running in the background, every minute, you will try to connect to your VPN!