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by: Bernard Teo

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Copyright © 2003-2012
Bernard Teo
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Sun 11 Nov 2007

From Postfix Enabler to MailServe for Leopard

Category : Technology/FromPFEToMSL.txt

While re-reading the previous post about testing MailServe for the Leopard 10.5.1 Developer Build, besides spotting a couple of grammatical errors (a weblog is performance art - mistakes are part of the art), I realised I forgot one huge chunk of the testing process - outgoing smtp, i.e., the process that sends mail out the server.

How can I ever forget that? This was the other bug I spotted on Leopard and it was only corrected at the very last developer release.

I couldn't get outgoing smtp authentication working on Leopard for a very long time. This is the process that authenticates your server with another mail server that you are trying to use as a Smart Host, so you can relay mail through it and not have your mail (coming, as it is, from a dynamic IP address) flagged as spam.

I needed to use this feature myself, so I set to debug it doggedly. Then I found it was due to a couple of files missing on Leopard and reported that as a bug and, thankfully, that was fixed by Apple in time for the final release.

So I test it now. But first, check that the domain name works by hitting the web server. Always check that you can actually hit the server, either via the web browser or via the command line by pinging it, before you move your mind onto the mail server. I can't emphasise that enough.

I have an image I hold in my head of problem solving as a series of concentric circles. Every step you take must shrink the number of possibilties, the number of possible errors, that you have to consider. Otherwise you're going backwards. With every step you take, the possibilities must converge, so you get to the point, eventually, where you're able to decide that it's probably this, or that, but no other. So the decision as to which step to take, among the many, is very important. Take the step that reduces the number of possible outcomes. I've found that when people come to me to help them debug their systems, most of the time I'm actually helping them devise a problem solving strategy. It's nothing more than that.

I first test that I can send mail out without using a Smart Host. See? Don't complicate things. Be patient. Take the step where the outcome tells you something definite - that you have a working smtp server that knows how to send mail to another mail server (even if your mail gets rejected eventually due to its contents, or due to the prevailing anti-spam rules at that particular receiving mail server). If you didn't even get this to work, there is no point testing against a smart host, with all the attendant complications with the authentication parameters.

Even if you're having to use the Smart Host feature because your ISP is blocking port 25, you can check that your mail server is actually able to send mail out by using a test setup on your local network, using local private IP addresses instead of domain names.

So if you're able to send mail the default way, next, make the server go through a smart host. If you know an smtp server that'll allow you to use it as a smart host without authentication, so much the better, test against it.

That worked, so I test against a server that does require my server to authenticate against it. And then I test it with SSL.

Because I have two broadband lines coming into my home, I do all my tests against my own live server ( on which I can set all sorts of conditions to act like any smart host would.

So, everything seems to be working on 10.5.1. But of course, I have to test it all again when the "real" 10.5.1 comes out for everyone.

So, I'm thinking. It really is a disadvantage calling my application Postfix Enabler, when it does so many other things beside enabling Postfix. It's like, I have the temerity to charge for something that others offer for free. But are they? Offering the same things, I mean. But like my auntie always tells me, life is too short for one to be resentful. It's a beautiful day out there. I have a date with my wife :-)

Posted at 5:44AM UTC | permalink

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