<nettime> Jody Ribtot: The Hostile Email Landscape

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The Hostile Email Landscape
October 17th 2015
Jody Ribtot

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.

Email today is dominated by a handful of major services. GMail
boasted 425 million active users back in 2012. Outlook.com has at
least 400 million users. It's become increasingly unusual for
individuals or businesses to host their own mail, to the point
that new servers are viewed with suspicion.

Earlier this year I moved my personal email from Google Apps to a
self-hosted server, with hopes of launching a paid mail service a
la Fastmail on the same infrastructure. I've done this before,
and this server was configured perfectly: not on any blacklists,
reverse DNS set up, SPF, DKIM and DMARC policies in place,
etcetera. (Side note: mail-tester.com and Port25 are great for
checking your setup.)

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.

The standard response from all of the above
boiled down to this, from Microsoft's Postmaster Troubleshooting
page:

	IPs not previously used to send email typically don't have any
	reputation built up in our systems. As a result, emails from new
	IPs are more likely to experience deliverability issues. Once the
	IP has built a reputation for not sending spam, Outlook.com will
	typically allow for a better email delivery experience. How to
	build a reputation for not sending spam when they're already
	flagging, bouncing, or deleting my mail was unclear.

In the end, I gave up and switched back to Google Apps. It felt
like defeat. This isn't how the internet is supposed to work. As
we continue to consolidate on a few big mail services, it's only
going to become more difficult to start new servers.

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