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The Hostile Email Landscape (liminality.xyz)
An anonymous reader writes: As we consolidate on just a few major email services, it becomes more and more difficult to launch your own mail server. From the article: "Email perfectly embodies the spirit of the internet: independent mail hosts exchanging messages, no host more or less important than any other. Joining the network is as easy as installing Sendmail and slapping on an MX record. At least, that used to be the case. If you were to launch a new mail server right now, many networks would simply refuse to speak to you. The problem: reputation. ... Earlier this year I moved my personal email from Google Apps to a self-hosted server, with hopes of launching a paid mail service à la Fastmail on the same infrastructure. ... I had no issues sending to other servers running Postfix or Exim; SpamAssassin happily gave me a 0.0 score, but most big services and corporate mail servers were rejecting my mail, or flagging it as spam: Outlook.com accepted my email, but discarded it. GMail flagged me as spam. MimeCast put my mail into a perpetual greylist. Corporate networks using Microsoft's Online Exchange Protection bounced my mail."
There's little more to the article than the summary.
How does the person in question solve their mail issue? They don't, they went back to Google Apps.
Now you don't have to read it.
I run my own mailserver, mostly "just because".
The reputation problem I encountered early on was because of a lack of a reverse DNS entry. Easily fixed; I simply asked my VPS provider to create one.
The next problem that started about 18 months ago was reputation: my little server simply wasn't a trusted service.
Because of the (unbelievable) amount of spam hitting my server, I had taken out a Comodo AntiSpam Gateway subscription about two years earlier. It was initially free, but after a year or so they wanted money. Since the service rocks, I happily pay my ~$30 annually.
What CASG also offers is outbound scanning: if I tell my server (an Exchange 2010 server) that the outbound smarthost is CASG, my email all of a sudden piggybacks Comodo's reputation. Voila, email flows without incident.
Problem solved.
I've been running mail system for myself for the past 5 years or so. Gmail has begun tagging my messages as spam, starting a few months ago.
I run my own mail server on a dyndns connection. At first, Google would filter out my mails, but once I set up SPF and DKIM records, they became much more friendly. Haven't tried outlook.com, but hotmail.com (also owned by M$) works fine.
I've been running my own mailserver since 2003, and I have seen my share of problems.
1: mailservers blocking mail based on spamhaus DUL. You can delist your IP. But still, blocking exclusively on that?
2: hotmail.com accepting emails and then discarding them silently. No trace of them. No bounce. Recipient did not have it in their spam folder or anything. This was several years ago, so perhaps it's better now. But discarding emails after promising to deliver them without any possibility for the recipient to control it: bad idea.
3: Various greylisting email servers. Not really a problem as my MTA will retry and the email is only delayed for a few minutes.
4: gmail.com rejecting emails sent over IPv6 but happily accepting them over IPv4. It turned out to be a problem with their parsing of SPF records, and apparently fixed now. But I did find out that there is no reasonable way to contact the gmail team.
5: outlook.com rejects emails due to FBLW15, whatever that means. It seems you can get whitelisted, but it appears that a lot of hosts are being hit by it for no reason.
6: office365 bouncing emails due to "protection" with no explanation given, and direction to contact the recipient by other means to get whitelisted. This was for a the official email address listen on a company website. I decided that my email wasn't important enough. Their loss.
Bottom line: If you run your own email server then expect to occasionally do some manual whitelisting etc. And expect some email servers to be uncooperative and/or RFC-clueless.
Try out https://mailinabox.email/, a project I began a few years ago to make hosting your own mail much easier.
It includes comprehensive diagnostics to ensure everything is configured correctly, including reverse DNS, which is the most common issue that leads to mail not being deliverable / going into spam. This doesn't solve every problem, but lots of people have had good results with this project.
When setting up email on my vanity domain, It took me about three hours to dot all my i's and cross my t's but Google has really good documentation and you can send/receive email to/from gmail without it being flagged as spam, then most anyone should also.
moox. for a new generation.
The OP wrote "this server was configured perfectly: not on any blacklists, reverse DNS set up, SPF, DKIM and DMARC policies in place, etcetera." Perhaps he deleted SPF and DKIM records after he gave up? However, the domain is registered by Contact Privacy Inc. Customer 0141536996, which I wouldn't deem a good start for a mail domain. The IP belongs to LINODE, a German Linux hosting place, and seems to be static. Only one black list, rbl.rbldns.ru, has it, which shouldn't be a major problem, but may suggest that some email problems did happen. He didn't subscribe to DNSWL.ORG either.
All that said, that conclusion is correct, IMHO. Microsoft in particular files all mail to the spam folder unless the sender is too big to block (TBTB). Even if I subscribed to their feedback loop, mail from an address they never saw, such as yyyy-mm-dd@my.example.com, is considered spam, no matter how many times the recipient whitelisted messages from the same domain.