Route 53 DDNS update have stopped working for me too Here is a post I made on Reddit r/PFSENSE. I got no replies there, so posting here as a reply in the hope that this will be worthy of someone's attention.
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When doing DDNS updates, the log says:
Jun 21 00:37:42 php-fpm 703 /services_dyndns_edit.php: Curl error occurred: Failed to connect to route53.amazonaws.com port 443: Operation timed out
Jun 21 00:37:42 php-fpm 703 /services_dyndns_edit.php: Dynamic DNS route53 (xxx.xxx.net): _checkStatus() starting.
To debug this, I noticed that earlier in the log, it showed the URL it was going to use for the update:
Jun 21 00:36:27 php-fpm 703 /services_dyndns_edit.php: Sending request to: https://route53.amazonaws.com/2013-04-01/hostedzone/--zoneID--/rrset
So I tried a curl to that url from the pfSense command line -- worked fine. So no idea why the connect is failing. Incidentally, I have no IPv6 enabled on the box. The aws log shows the last successful update was about 45 days ago, I think when I was still on 2.4.4 which is why I'm worried this might be a 2.4.5 or 2.4.5-p1 bug.
UPDATE:
This appears to be related to routing, please see further info in the related post just made in the routing area