Automatically Reconnect to a VPN on OS X
For some reason, the built in VPN tool on OS X doesn’t reconnect if the connection drops. The following snippet of AppleScript will fix that:
on idle
tell application "System Events"
tell current location of network preferences
set myConnection to the service "VPN NAME"
if myConnection is not null then
if current configuration of myConnection is not connected then
connect myConnection
end if
end if
end tell
return 120
end tell
end idle
Plonk the above in AppleScript Editor (replacing VPN NAME with the Service Name you entered when configuring your VPN) and save it as an Application with the ‘Stay Open’ option checked.
Source: Ask Different