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Terry and I eventually gave up on this Sendmail book—too hard—and had to bring in a consultant on a colleague’s payroll.

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@tejr do you have an academic or commercial interest in Sendmail? I recall, back around 2000, we brought in an external Sendmail specialist (my CF skills were fairly weak) to help integrate a legacy Data General system (used by the health sector) with a modern Postfix server via UUCP... was surprisingly painful to get right... but then it worked flawlessly for a decade +...

@lightweight I’ve never had to implement Sendmail. I’m a Postfix babby, so the most I’ve had to do is fight with its compatibility mode with its /usr/lib/sendmail compatibility interface. Hearing some war stories, I feel like I was fortunate.

@tejr the first commercial email systems I ran were Sendmail, moving quickly to Qmail (due to the complexity of tweaking anything Sendmail) which had to be compiled constantly due to being developed by Daniel J Bernstein... (Also ran DJBDNS, for my sins) and eventually, with a huge sigh of relief, Postfix came onto the scene. Still running it these days, mostly wrapped up in Mailcow Dockerized... a superb solution.

@lightweight @tejr Not a fan of postfix, the log data are difficult to interpret. And I really dislike the non-normalised config files, where you can put important statements anywhere in there. Much more a fan of exim :-)

@yojimbo @tejr we're spoilt for choice. At some point, the best one is the one you feel confident implementing and maintaining. For me, that's Postfix (I've had some unhappy experience with Exim, which I've also maintained over the years).

@fikran @tejr It's complexities have morphed substantially over the past 20 years... now the main complexity is achieving credibility from the perspective of other mail servers....

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