One of my irritations: outgoing email that was scored as spam
When I was setting up our mail system, one of the questions I asked myself was whether we should run our outgoing mail through our spam scoring system. Then I came to my senses.
You see, one of the things that I find really irritating is getting a spam message that has been thoughtfully scored as spam by the sending mail system. It adds that little extra bit of smug salt to the wound; sure, the sending system knew it was spam (and therefor bad) but so what, they decided to deliver it anyways. It's bad enough to unknowingly deliver a bad message, especially in today's world, but it's actively antisocial to knowingly do so.
(I'm not talking here about systems that are forwarding email for me; this is about outside machines that originate or at least relay spam to me.)
Of course, I understand that this is not malicious (one could quibble about whether it qualified as 'deliberate'). Generally I expect that one of three things is happening: either the people involved have never thought about this (perhaps they did not expect their webmail system to get compromised), or they are using software that gives them no option to block the messages, or there has been a political decision made that outgoing messages simply can't be blocked regardless of what the spam scoring system thinks about them.
From the outside, none of that matters to me. What matters is that they clearly and visibly had a chance to stop me getting spammed and they chose not to do so.
This is why I consciously chose not to run outgoing mail here through our spam tagging system; I expected that in our environment there was essentially no chance that we could get approval to block outgoing email that the black box of our spam tagging system didn't like.
(I suspect that this is especially so because, like so many other places, outgoing spam is simply not supposed to happen; protecting against something that's basically a once every ten years event at the expense of some non-zero level of false positives is, well, a hard sell to many people.)