Why Is Email So Hard?

I want programs on my machine to be able to send mail. Surely that’s not too much to ask. If I wanted it to Tweet, I’m sure there are a dozen libraries out there I could use. But sending mail… that requires the horror that is sendmail.rc or trying to configure Postfix or Exim, which is the approximate equivalent of using an ocean-going liner to cross a small creek.

Or does it? I just discovered “ssmtp“, which is supposed to be a program which does the very simple thing of accepting mail and passing it on to a configured mailserver – GMail, your own, or whatever. All you have to do is tell it your server name, username and password. Simple, right?

Turns out, not so simple. I kept getting auth failures, whichever server I tried. ssmtp’s verbose mode seemed to show no password being shown, but that’s because it doesn’t show passwords in logs. Once I finally configured a mailserver on port 25 (so no encryption) and broke out Wireshark, it turned out that ssmtp was sending a blank password. But why?

The config file doesn’t have sample entries for the “username” and “password” parameters, so I typed them in. Turns out, the config key for the password is “AuthPass”, not “AuthPassword”. And ssmtp doesn’t think to even say “Hey, you are trying to log in without a password. No-one does that. Are you sure you’re not on crack?” It happily sends off a blank password, because that’s clearly what you wanted if you left the password out entirely.

<sigh> There’s 45 minutes of my life I won’t get back.

3 thoughts on “Why Is Email So Hard?

  1. And about additional 10 minutes to write this blog post. :) Have you made sure to file a bug or let them at least know about this problem? Just so that others are not trapping into the same problem and loosing valuable time of their life.

    • Henrik: I would, but I can’t find where the upstream is! I guess I could file the bug in the Debian BTS…