IPSEC VPN not connecting automatically from main site



  • I have a ipsec vpn site to site tunnel configured in main mode and when I ping a machine at the main office the tunnel will come up no problem, I can then ping any machine on either LAN from either end and have no problem with RDP or email or any other connection.

    What I can not do is get the tunnel to connect automatically when I ping the remote site from the main office and this is a must.

    I can get iphone to connect to pfsense also no problem

    The main site is an ASA5505 the remote site is pfsense configured router.

    I am stumped, pfsense is configured the same as the CISCO RV042 that it will be replacing, ( RV042 can not handle iPhones ), the CISCO will come on line when either network is ping and tunnels will come up automatically.


Log in to reply