The other day one of our Corporate Members (an e-tailer) contacted us to ask if we had any good contacts at MSN / Hotmail to try and resolve an e-mail deliverability problem they were facing. 

Namely, that none of their e-mails to Hotmail addresses were getting through – none, not even order confirmations etc.

How did they spot this? Because their Hotmail customers were complaining to them that they weren’t getting order receipts and so on. How big a problem was this? About 25% of their customer base used Hotmail addresses. So big. Really big.

The full saga follows, but the short story is:

• You don’t get any notification from MSN if your Hotmail e-mails are being rejected. No bounces, nothing. They just disappear. Only testing, monitoring, tracking (or angry customers) will flag the problem.
• We found out that our Hotmail e-mails weren’t getting through (have you checked yours recently?)
• If you are commercially sending e-mails to Hotmail addresses it appears increasingly that you either have to sign up to the Bonded Sender program or you have to use an E-mail Service Provider (ESP) if you want your e-mails to get through reliably.

So, back to our beleaguered e-tailer…

For starters, in order for MSN to investigate anything you will need to go to the MSN Postmaster site. In the troubleshooting section you will find a list of information they will require from you, as follows:

1. What are the IP addresses of your outbound mail servers?
2. What operating system, mail transport software, and/or mailing list management software are you using?
3. How are "bounce messages" (non-delivery notices) handled by your system?
4. How frequent are your mailings?
5. What are some of the accounts on Microsoft's systems that you are attempting to send to?
6. Do your SMTP logs show any failed transactions when attempting to send to addresses at MSN, MSN Hotmail or other MSN Services? If so, please include them inline in your response.
7. Can you telnet to port 25 of mail.hotmail.com and/or mail.msn.com from your mail server(s)?
8. Can you traceroute to 216.32.183.201 from your mail server(s)?
9. Please include samples of a few of the messages you are sending, with complete headers (as seen by your recipients.)
10. In what manner(s) are recipients added to your mailing list(s)?
11. Provide the URL of your web site.
12. Provide the URL of your Privacy Policy.
13. Provide the URL at which users opt-in to receive your mailings.
14. Provide the URL at which users may choose to permanently unsubscribe from your mailing list.

Having dutifully compiled all the above information, our e-tailer managed to track someone down at MSN Hotmail. There then followed a series of e-mails, from various different people, which seemed to give somewhat conflicting views on Hotmail’s approach to whitelisting:

“We do not employ any form of white list to our incoming email” 
“Bonded Sender (www.bondedsender.com) is the only White Listing service to which we subscribe.”

Official documentation on the Postmaster site and elsewhere states:

“"False positives" refers to e-mail that has legitimate content and which adheres to the technical standards, but is incorrectly flagged as junk e-mail by the junk e-mail filters. Such e-mail is delivered to the recipient's Junk E-Mail folder. Hotmail's solution for addressing this issue is the Bonded Sender program.”

“At Hotmail we do not maintain our own white list.  However, Microsoft accepts e-mail messages that may be allowed to bypass some of Microsoft’s filtering technologies from organizations that are approved by the Bonded Sender Program (www.bondedsender.com), powered by Return Path and certified by TRUSTe.”

“Mail sent from senders that are enrolled in the Bonded Sender program skip much of the Hotmail anti-spam filters.”

My reading of all this was “if you’re sending commercial e-mails to Hotmail addresses then the only reliable way to get through is to sign up for the Bonded Sender program”. And even that might not work.

By this time I also started thinking, maybe our e-mails to Hotmail addresses aren’t getting through either? 

Of our 30,000 odd registered users only just over 2,000 have Hotmail addresses but that’s still 7% of our users. Worse was the thought that someone might subscribe to our site and never even get their order confirmation because it evaporated into the ether.

So we did some analysis of open / response rates for our Hotmail users. And we set up some tests to send our e-mails to Hotmail accounts we created….

Guess what? 

Not a single Hotmail e-mail we were sending was getting through. Like the e-tailer, we use our own in-house mail server, and we have always striven (like the e-tailer) to follow best practice and be “whiter than white”. We’d followed all the latest best practice, like making sure our mail servers had full DNS information etc.

So this came as something of a shock.

So what were we to do?

• Go to an Email Service Provider (ESP) who’d sort this pain out for us?
• Copy the spammers and just change the IP address of our mail servers now and again?
• Sign up for the Bonded Sender program and hope that sorted things?
• Contact MSN Hotmail and get them to unblock us?

Given we like to try and experiment on ourselves with the latest best practice, industry programs, certification and so on, we thought we should at least sign up for the Bonded Sender program.

This is something you have to pay for so it did feel somewhat like having a gun held to our heads – you can follow best practice all you like but you still have to pay for the right to e-mail Hotmail users?

So we filled out all the relevant information to apply for the Bonded Sender program. To our dismay the reply came back a few days later:

“We've looked at the volume and complaints for those IPs and unfortunately, we have some bad news. Based on our preliminary valuation, we cannot forward your application on to TRUSTe for certification at this time.

Reason:

Excessive complaint rate.  The complaint rate of 2.18 over 842,706 for the IP address(es) specified in your Bonded Sender Program application exceeds the allowed level of 1 complaint per million as defined in the Participating Sender License Agreement.

While you are welcome to reapply, we will not be able to accept another application for you for a minimum of 90 days, during which time we would like to see a reduction in complaints.”

Frankly, I was amazed that we’d *only* had 2 complaints from almost a million e-mails.  It turned out that the complaints were from SpamCop and came in just one month. Who knows what those complaints are, or why. Or who is meant to judge whether a complaint is valid or not?

 There were a couple of further ironies here it seemed to me:

• Firstly, we have been registered with TRUSTe for 4 years so far. So to be told our application couldn’t be forwarded to TRUSTe for certification seemed strange.
• Secondly, if the complaint threshold is based on a ratio then the easiest way to get round it would be to just blast out loads of e-mails to some tame / dummy addresses to flatter your percentage of complaints.

Certainly the second point plays to the Email Service Providers again. They might get a lot of complaints but they disappear (ratio-wise) into the ocean of volume of e-mails they’re sending.

So what have we done…?

Well, we’ve managed to persuade Bonded Sender to reconsider our application within 30 days rather than 90.

And we’re temporarily using an ESP to send e-mails to Hotmail addresses. Which feels like cheating when we shouldn’t have to.

Anyone else have further insight into the latest deliverability challenges…?

Ashley Friedlein
CEO, E-consultancy.com