pfsense: dynamic dns doesn't update automaticaly - it knows it's outdated

Solution 1:

It appears that this is a known limitation[1] when pfsense is connected with your modem/router using TCP/IP (either static or dynamic). The workaround is this:

Install the cron package (System > Package Manager > Available Packages, search for cron and click INSTALL). Then go to Services > Cron and click edit(the pencil) on the line about rc.dyndns.update. You need to change the Minute to */5 and Hour to *. This will make pfsense to check for IP changes every 5 minutes.

Notes [1] There is a closed bug report https://redmine.pfsense.org/issues/2148 where the pfsense team suggests this workaround. They feel that the issue affects such a tiny share of pfsense users that it's not worth fixing.