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No iussue come up in the health check. I have an update though, after messing around with just about everything and several reboots, now all of a sudden the header_checks_receiving file is now populated with the rules... however... When I add new rules via the GUI they are NOT added to the file. Any idea what process / script is responsible for taking the entries from the UI and generating the headers file? Also this seems to be very similar to an issue I am having with aliases where sometimes they do not seem to update until I reboot.

I do not see any postfix related errors in the backend system logs, all postfix changes seem to apply correctly.

Anyone have any ideas?

I am trying to troubleshoot through some issues with header checks, I've read all I can about how to format the regex properly and I think I've got that right, so for example:

/^From:.*twitter.*/ REJECT rejected

But I still get mail from twitter.com. I've tried many many variations of the regex and nothing seems to work. In digging in further it seems like the postfix mail.cf in /usr/local/etc/postfix is pointing to:

header_checks = regexp:/usr/local/etc/postfix/header_checks_receiving
smtp_header_checks = regexp:/usr/local/etc/postfix/header_checks_delivering

No matter what I do in the GUI (enable, disable rules, use the example regex, etc...) Those two files are completely empty

This makes it impossible to "test" the header checks using postmap which is supposed to be something like:

postmap -q "<put test header here>" regexp:/usr/local/etc/postfix/header_checks_receiving

Obviously this doesn't work. So I'm kind of stuck, I'm not sure how to test my rules and I don't know why those files are blank. Any assistance would be very much appreciated.