Deliverability 101, Delivery Essentials

Deliverability 101: The Big Three

For over a decade now, those of us who work in email have talked about the “Big Four” email providers. This was used to refer to the four largest providers of consumer mailboxes in the industry: Microsoft, AOL, Google, and Yahoo. In online discussions and on email distribution lists, they were often known by the keyboard-friendly acronym MAGY. Early this year AOL and Yahoo merged under the Oath brand, whittling the Big Four down to three and prompting a new acronym: OMG.

For years, each of these companies has provided free email accounts to anyone with internet access and a few basic personal details to hand over. They (mostly) provide free webmail with virtually unlimited storage, while using the personal data of accountholders to sell advertising that gets displayed within their respective user interfaces. It can often be difficult for senders to identify and/or troubleshoot delivery issues, as each provider’s primary duty is to their users and advertisers and senders can get left out in the cold when searching for answers. Here’s a brief primer on each of the Big Three to help you along.

Microsoft (Outlook.com, Hotmail, MSN)

microsoft

If you’re reading this on a computer, you’re probably familiar with Microsoft. As the purveyor of Windows, their name is found on most of the computers in the US today and they’ve been providing free email since 1997.

Starting as Hotmail then eventually rebranded to Outlook.com email, Microsoft’s freemail offering remains one of the most popular.

Troubleshooting

Microsoft provides a number of tools for senders to monitor and troubleshoot delivery to their users. Signing up for their Feedback Loop (dubbed the Junk Mail Reporting Program or JMRP) is a must to ensure you receive complaint data from MS. Integrated with JMRP, Smart Network Data Services (SNDS) provides senders with insight and daily monitoring of their mail delivery performance. Instead of discrete numbers, SNDS uses a color-coded system: Green means that more than 90% of your mail went to the inbox, Red means that less than 10% made it to the inbox, and Yellow indicates something in the middle (generally closer to Red).

The provider recently started to merge their consumer offering Outlook.com with Office365, their business-class email solution, but still offers separate remediation processes for each service. While there are rumors of the Outlook.com support form working for both products, no official confirmation has been issued. Until it is, the Office365 Delist Portal should be your first stop for problems sending to corporate domains using hosted mail.

It’s also important to note that the filtering for each product remains separate – SNDS does not include data from Office365 and B2B mail may be routed differently than B2C, even from the same sender.

Oath (AOL, Yahoo, and Verizon mail)

oathWhile Oath is technically the newest company on the list, their email offerings have been around for quite some time. AOL (originally America Online) provided dial-up internet and email service to millions of users in the mid-1990s, then began to offer their webmail for free to non-AOL users in 2006. Yahoo started its email service in 1997 with the acquisition of the Rocketmail platform. In late 2017, the two services were merged and became Oath.

Troubleshooting

Prior to their merger, AOL was known for being one of the most responsive providers when seeking assistance. They offered an online reputation tool, a remediation form that generally received quick responses, and a knowledgeable, helpful Postmaster team. Yahoo was known to be a bit more of a black box when troubleshooting delivery issues, although their bounce messages and the troubleshooting pages associated with them were fairly descriptive.

Since the merger, mail to both AOL and Yahoo addresses are being directed through Yahoo’s mail servers. Many of the most common Yahoo bounce responses are now being seen with AOL addresses, and Yahoo’s Postmaster documentation and support form (login required) are the de facto method of receiving support for delivery issues.

Google (Gmail)

googleGoogle’s Gmail offering is the youngest of the Three, having been introduced via private beta in 2004. Experiencing meteoric growth, it eventually overtook Yahoo and Microsoft to become the most popular freemail provider in 2012. Today, Gmail addresses typically make up a significant portion of any consumer email list – often more than half.

Troubleshooting

Unlike the other providers on the list, Gmail offers no direct method of contact for senders. Their filtering is almost exclusively automated, so even if you know who to contact they’re generally unable to make any changes to the routing of your email. Fortunately they do offer some useful tools for monitoring your delivery performance. Google’s FBL, unlike those provided by other major players, does not pass back specific subscriber data but only aggregate complaint numbers. You can also track these FBL complaints, your IP and domain reputation, authentication status, and mail error rate via Google’s Postmaster Tools.

Because of their unconventional FBL, it’s not possible to identify and suppress those recipients who mark your messages as spam. You’ll instead have to use the data available to you (opens, clicks, site visits from email, etc) to determine if your recipients are engaging with your messages. If you experience delivery issues to Gmail, check the composition of your list. Are most of your Gmail recipients ignoring your emails (no opens recorded in 6-12 months)? If so, that’s likely the cause of the issues. One word of caution when dealing with Gmail: once you start to see problems, it can take weeks or longer to resolve them, so it is generally best to keep your lists clean proactively.
While there are hundreds of mailbox providers out there, these three often make up the vast majority of a sender’s contact database. Learning how to effectively navigate the Big Three is a major step toward mastering your email deliverability.

– BG

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Industry Updates

Changes

bowie-change
courtesy securosis.com

New year, new you…that’s what they always say, right? Just a few weeks into 2018, it seems like some of the big 4 ISPs (soon to be Big 3?) are really taking that concept to heart.

Microsoft’s major migration of Outlook.com to the Office365 backend was technically completed in 2017, but based on feedback from senders in industry groups delivery issues still abound. The indications from MS are that the mail handling and filtering infrastructure are a work in progress, but no formal statement has been issued to that end. Some senders have stated MS support is unable to provide remediation for many of these issues, even though there may be backend adjustments taking place. If you’re having trouble getting mail to Microsoft, just know you’re not alone and that someone over there is paying attention.

Verizon ended its own webmail service last year, and consolidated its AOL and Yahoo brands under the Oath moniker. AOL and Yahoo’s email services have remained separate thus far, but indications are that will change in the next few days. It’s been reported that the merger of these mail platforms starts in earnest on or around February 1st. As of that date, mail to AOL will be routed and handled by the Yahoo mail servers. To me this sounds a bit like the SBCGlobal arrangement between AT&T/BellSouth and Yahoo, wherein one provided the mail interface while the other handled the mail routing and filtering. At this time, no formal announcement has been made, so we’ll have to sit tight to find out exactly what this means for sending to AOL recipients.

– BG

Best Practices, Industry Updates

Microsoft rejecting your mail? You may be suspected of email harvesting

www.volganet.ru [CC BY-SA 3.0 (http://creativecommons.org/licenses/by-sa/3.0) or GFDL 1.3 (www.gnu.org/licenses/fdl-1.3.html)], via Wikimedia Commons
via Wikimedia Commons
If you’ve been noticing your mail is rejected by Microsoft lately, it’s a good idea to take a look at the Smart Network Data Solutions (SNDS) dashboard. If you’re not aware, SNDS is Microsoft’s tool to show senders how their mail performs to recipients at MS domains. You can sign up for free (assuming you own your IP addresses); if you use an ESP, they’ll have SNDS set up for your sending IP and generally monitor it regularly.

If you do have SNDS access, you can check the IP Status¬†heading to see any blocks that are currently in place for the IPs you own. Over the past few weeks I’ve been seeing a lot of IP addresses listed there due to “E-mail address harvesting.”¬†After working with the Postmaster team, it seems the issue occurs when too many RCPT commands are sent without valid recipients. In other words, the sending server attempted to validate the existence of a lot more email addresses than they actually sent mail to. These blocks are most commonly associated with dictionary attacks, or sending to many usernames at the same domain (aaa@domain.com, aab@domain.com, aac@domain.com) with the purpose of finding good addresses. This tactic is often used by spammers who are – you guessed it – harvesting email addresses for their mailing list.

However, the instances I’ve seen have all been legitimate senders, sending mail to people who have signed up to receive it. In one case, a human error led to sending mail to a list of unsubscribed addresses, but the rest appear to simply be senders whose list hygiene needs improvement. In addition to dictionary attacks, these blocks seem to be triggered by high rates of invalid recipients. These recipients are counted in the number of RCPT commands but not in the total delivered. In one case, the difference between the two was only around 10% – certainly not ideal, but also not indicative of a spammer harvesting addresses.

When working with the Postmaster team, they’ve been very helpful in getting the blocks resolved once we explain the circumstances around the sends and how we’ve taken steps to prevent a recurrence, but these blocks have stopped all mail to Outlook.com users for days in some cases before they are removed. For a sender, this could mean a substantial loss of revenue while the block is in place…so what can you do?

Now more than ever, list hygiene is paramount. Be sure you aren’t sending to old or stale contact lists and target recipients with recent open or purchase activity. Keeping your bounce rates as low as possible will minimize the chances you run into one of these MS blocks.

Been flagged as a harvester yourself? Just having trouble getting delivered to Outlook? Let me know in the comments or via email!

– BG