I am not sure when this stopped working but I just noticed that none of my Dynamic DNS clients (OpenDNS or Cloudflare) are working.
In my pFsense logs I see the below after trying to update these clients,
There was an error trying to determine the public IP for interface - wan (igc0.10 )
From within my network I can browse out and ping items. I can also reach self-hosted sites from outside my network with no problem (until my external IP changes).
When I look at the Interface status page, the WAN is showing the correct external IP.
Also, not sure if this means anything but running
from Diagnostics → Command Prompt returns the correct external IP.