Estou usando este script para a reconexão automatizada da vpn
on idle
set vpn_name to "'cloud.lietaer.net'"
tell application "System Events"
set rc to do shell script "scutil --nc status " & vpn_name
if rc starts with "Disconnected" then
do shell script "scutil --nc start " & vpn_name
end if
end tell
return 10
end idle
Tente o ponto # 4: transmitir