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by dspillett 1509 days ago
> and I tend to be unsure how bad it actually is: sometimes it does seem pretty bad, other times it sounds like it's fine

That is pretty much it. One factor is that once you are on a blacklist it can spread like wildfire and be much faf to get off them all again, so the risk is small but the hassle if it happens is high. Also if you send mail for numerous people there is going to be a much higher risk: every extra user/account/address is an extra hack target (do all your users have good, non-shared, passwords?) or just extra volume that might be accidentally classified as junk (and once something from your server gets classed that way, future content may get more aggressively analysed and more mistakes may happen).

I've run my own mail server, including sending mail directly, for many years and to my knowledge not had a significant delivery problem. But I have a few mitigating factors: the IPv4 address is essentially on a commercial ISP range, not one that looks like a residential account or a VPS service provider, and the ISP is one that takes junk mail seriously, so there is less “splash damage” potential, and the same range has been used this way for several years (the main sender has moved around that small range, when testing upgrades on a copy VM for instance, but never away from it entirely) so it never looks like a brand new mail server these days, I only serve myself and a very small number of other users, our outgoing mail volume is pretty low.

It is a bigger problem for hosting services (much bigger user-base and little control over what they might send) or if you are sending from one of their ranges, if sending from a residential ISP address range, if your volume is high (perhaps you have apps that send mail as well as your personal mail?), etc., but it can be a problem for everyone.

I'm rebuilding my mail service soon (moving off Zimbra to just configuring the parts myself, as we don't need the extra features these days, it is too chunky for just a mail server, and at the end of next year they stop releasing easy install packages for the non-paid users (they already have for v9., next year v8. hits EOL)) at which point I might reconsider where it is hosted and if I should be sending via a paid SMTP relay to let them worry about deliverability, though as far as I know I've not had a problem.