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Comment by teddyh | Hacker News Reader

I sometimes see similar tales of woe, and I can only say that this does not match my experience. I’ve done this many times, you set up the mail server, configure DNS correctly (including reverse lookup), and that’s it. Never had problems being blacklisted or mail getting classified as spam.

I suspect that people having trouble are sending a lot of mail, like “newletters”, etc. But I can’t prove this hypothesis.

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Mail reputations are very real and pose an issue with mail servers. I had a gaming server for years and had many issues with Gmail, Microsoft and Yahoo, to name a few, filtering or blocking emails. Just last week, I setup a mail server using mail in a box on a new server I spun up on Digital Ocean using an IP that was on no blacklists and still had issues with sending emails to various Gmail subscribers.

Even when I used to work at HostGator and handled many of their abuse issues, they had many issues with being blacklisted just because RBLs didn't recognize new HostGator IPs or the rate of email being sent from their new gateways.

So, at least with my personal and professional experience, I can attest to the issues with using self-hosted mail servers.

One more point of data from my experience: I have never set up mail servers at hosting providers in remote datacenters, only local servers in my own server rooms which I could physically touch. I guess it’s quite possible that Gmail, etc. have figured out by now where all the IP blocks of hosting providers are, and are very suspicious of them.

New IPs are often old IPs that have been used for other purposes before, and often blacklisted. Especially IPs on easily spun-up and spun-down hosts like DO. On DO, after every VPS I've removed, and then started up another a week later, it has a different IP. It would be easy for a spammer/phisher/whoever to abuse this quick address re-allocation, but hurts regular users.

Ack. Same here. I had a mail server colo'd with Peer1 in Canada since mid 2000's, which I moved to a European colo few months ago. I use it to periodically send newsletters to few thousand people, so it's not exactly low-volume.

The one and only issue was with some AT&T block list - and judging by their supporting forums they end up with a boatload of false positives - I filed a complain with them and they removed the block few days after.

I suspect that OP ended up getting an IP from a netblock that has lots of transient customers, which included some spammers. It's not his server's reputation that was weak, it's the netblock's rep that was bad.

I've had similar issues to those described in the article. Especially "outlook.com accepted my email, but discarded it."

When people buy my book, I my server sends them literally one single email containing a link to the PDF they have purchased. And that's it.

Google delivers my email fine, in most cases. But hotmail/outlook was just deleting them most of the time for over a year.

I know I'm just a single data point, but I swear I'm not a newsletter!

Exchange is much more discerning of email structure than Google servers.

That means that, if you have any configuration mistake, an Exchange server will reject your email. But if you have a good reputation, Gmail will deliver it anyway.

Exchange servers weren't "rejecting" my email. They were giving me SMTP 250 (Queued mail for delivery) then silently failing to deliver it.

Hotmail sender support kept saying "I do not see anything offhand that would be preventing your mail from reaching our customers from this IP"

Also, my emails were and are text/plain.

I'm sure Exchange does reject malformed emails, but that wasn't my problem.

My experience with a malconfigured server interfacing Exchange is that Exchanges pretends everything is ok while receiving (with a 250 response at the end), and may sometimes notify its user (with a bounce message) while sending, but may also not.

But, of course, YMMV. And I have no experience at all sending email to Hotmail. I just thought it was worth checking your server settings.

I think I might be able to offer another explanation.

People talk about the reputation of their individual IPs, but networks matter a lot too. DigitalOcean for instance is an occasional source of spam; Linode is very rarely; 1and1 is a HUGE headache; and so on.

I have some custom software in place that temporarily drops entire netblocks for abuse, and I did that to keep up with the spam filtering offered by larger services. With so many spammers now switching between cheap VPS hosts, it was getting impossible to do single-IP-only bans.

Ever since the software was put into place the amount of spam actually making it into users mailboxes has fallen off a cliff.

You have to be very very careful about which network you choose to host your mail server from.

I was actually hosting on Linode (UK). My hunch was that they would be one of the more reputable networks; I've run small mail servers on them before (2+ years ago) without any problems.

It's a pity there's no easy way (that I know of) to look up the reputation for an entire network block. I'm glad to hear your experience with Linode matches mine.

It's different from one AS to another. I've spent a lot of time maintaining reputation for my IP at a certain major ISP (no bulk email) and I'm still getting blocked from Google and others.

Then I got a VPS at Linode (for some other purpose), installed Postfix and emails were just working - no SPF or even reverse DNS set up.

IP reputation IS a thing.

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