I’ve noticed a lot of people have had an issue with Postfix, saying the error log mentioned “Too Many Hops”. I had the same issue, using my Postfix, Spamassassin setup. It seems every time Postfix is updated, tweaking is needed to make it work again.

What was going on, is that the main.cf and master.cf were sending messages back and forth to each other. Before, lots of people had the same setup were you would set the content filter in the main, and master files. Simply commenting out “#content_filter = spamassassin:[]:10025” from the main.cf, and leaving this in master.cf:

smtp      inet  n       -       -       -       4       smtpd
           -o content_filter=spamassassin
 spamassassin unix -     n       n       -       -       pipe
         user=spamd argv=/usr/bin/spamc -f -e
         /usr/sbin/sendmail -oi -f ${sender} ${recipient}

I hope this helps out people with the same issue. If not, always disable your spam/virus software just to see if you can get send mail without the error.