Configuring Postfix in Mac OS X 10.5 Server with Dyn Standard SMTP

As a happy user of MailServe Pro on Mac OS X 10.5 Leopard “client”, I was assuming my migration to Leopard “Server” would be worthwhile by getting a more capable admin GUI for the built-in Postfix mail server. So far, it’s been a little more complicated than that.

In this configuration, I’m using Dyn Standard SMTP to relay SMTP and configured the 10.5 Server Admin accordingly:

But when I send mail, I get the following error in the SMTP log:

postfix/smtp: warning: SASL authentication failure: No worthy mechs found

Great. After double checking the password, authentication settings, port, etc., it turns out the lovely Server Admin GUI (a major driver for the upgrade) is a little buggy when it comes to editing the Postfix config files. Reading closely in the FAQ from Dyn, you have to manually edit /etc/postfix/main.cf by adding:

relayhost = outbound.mailhop.org:2525
smtp_sasl_security_options=

Mind you editing config files is exactly what I was hoping to avoid with Server Admin. In fact, this worked fine in the prior setup using the client OS with MailServe, no edit required. I plan to post more about the server setup and why I’ve chosen vintage equipment to run it on, but for now I need to document some of the gotchas of this upgrade. I hope this is the last post!

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