Have you tried setting up a scheduled ping to the other side?  Pfsense now has an option to do this.
 I have used this trick successfully from a workstation or server for a long time in similar
situations.  

------Original Message------
From: Michael
To: m0n0wall
Subject: [m0n0wall] IPSec and dynamic DNS
Sent: Jul 28, 2010 6:34 AM


Hello list,

My routers have a dynamic DNS - IPSec problem.

Premise 1:
My m0n0wall 1.32 embedded (on Alix 2) router called 'tokyo.mynet.com'
correctly forwards over a IPSec tunnel to 'madrid.mynet.com'.

Premise 2:
tokyo.mynet.com is correctly updating the master DNS server for
mynet.com with a dynamic IP address which changes every day.

Premise 3:
madrid.mynet.com has a static IP address.

Problem:
After the IP address for tokyo.mynet.com changes, everything
continues to perform normally, however IPSec fails.

Diagnosis:
Looking at diag_ipsec_spd.php and diag_ipsec_spd.php on
tokyo.mynet.com, everything looks good. Entries in SAD are torn
down when unused, and entries in SPD always contain the current
(correct) IP address.

On the remote (static ) router madrid.mynet.com, I see that the
SAD entries are never torn down and the SPD entries contain the
old IP address for tokyo.mynet.com.

I've already activated dead peer detection (DPD). What else do
I need to do to get this working?

Thanks,
Michael

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--
Kevin Tollison

Sent from my Blackberry