Jan 26

Ever tried sending mail from your own server and ended up on the Spamhaus Policy Block List (PBL)? I have, a couple of times.

From my FreeBSD sever, I get daily emails; “daily run output” and “security run output”. I’m not particularly interested in these, but it’s important that I get SMART notifications.

What I noticed is that whenever my IP address changes (every couple of months) the emails start coming through again. If you look at the mail log (/var/log/maillog), you’ll see something like
Dec 24 03:14:24 myhostname postfix/smtp[6740]: 9B8A5CB111C: to=<user@example.com>, orig_to=<user>, relay=smtp.examplehost.net[x.x.x.x]:25, delay=43, delays=0/0.22/21/21, dsn=5.0.0, status=bounced (host smtp.examplehost.net[x.x.x.x] said: 550-"JunkMail rejected - me.exampleisp.com (myhostname.mydomain.net) 550-[x.x.x.x]:63909 is in an RBL, see 550 https://www.spamhaus.org/query/ip/x.x.x.x" (in reply to RCPT TO command))

So nicely, they’ve given a link to lookup why you’re blocked. In my case it’s due to using an unauthenticated mail port (25). Since I had this problem before, I though I had setup authentication but in the FAQ it’s very clear that you cannot get this error if you have authentication enabled.

So what else does does it say in the mail log? Well, just before that line:
Dec 24 03:13:54 myhostname postfix/smtp[6753]: warning: smtp_sasl_auth_enable is true, but SASL support is not compiled in

This is a problem with the Postfix package for FreeBSD. I can’t find any other way around it other than to compile Postfix yourself from Ports. Here’s a link to the (unresolved) request in FreeBSD Bugzilla to add a package with it compiled in. So if you’re looking for a FreeBSD package with SMTP SASL authentication – give up (unless that bug has been resolved since the time of posting).

I’m not going to go into details of how to set up the SMTP + SASL on FreeBSD, there are already many guides that do that. I found these helpful:

One other small roadblock I ran into was trying to use port 465. When checking my web host, they specify that port of authenticated SSL, but I found the following error in the logs:
CLIENT wrappermode (port smtps/465) is unimplemented
instead, send to (port submission/587) with STARTTLS
status=deferred (lost connection with smtp.examplehost.net[x.x.x.x] while receiving the initial server greeting

My host didn’t give any indication that it supported SMTP on port 587 and if you search for this problem on the web you’ll find many people trying to solve it with stunnel. A quick telnet to my host on 587 showed it was open, so I just gave it a try. Lo and behold Postfix authenticated and sent my mail. So give port 587 a try even if you’re recommended to use 465 for your relayhost provider.

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