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

Oath update: AOL, Yahoo, Verizon MTAs and FBLs

Last week, the Oath Postmaster blog published an update on the status of their email migration. AOL (who previously absorbed Verizon’s email) and Yahoo are moving closer to their end goal of a unified email platform under the new Oath brand.

According to the post, all mail sent to either brand is now “handled by…OATH MTAs.” So when you send to any address at aol.com, aim.com, verizon.net, yahoo.com, or any other domain controlled by these providers, the mail is all routed through the same system – including spam filtering. Reports have been surfacing on some industry forums of AOL bounces for Yahoo addresses and vice versa. As a sender, this also means you should start aggregating these domains for your reporting purposes. Monitoring complaints, bounces, and other metrics for anomalies should consider Oath as a single entity – word on the street indicates most ESPs have already begun this process for their customer monitoring.

In addition, spam complaints for AOL recipients will soon be received via the existing Yahoo feedback loop. Since Yahoo’s FBL is domain-based, all mail to AOL addresses must be DKIM-signed to participate in the FBL (if it isn’t already). If you use an ESP that hosts your DKIM, they may need to double-sign to ensure all FBL complaints are received.

So far, the Oath Postmaster blog and their participation in various industry channels have provided regular updates on the migration. Let’s hope that pattern continues as the two current Postmaster sites are combined into an upcoming Oath Postmaster resource.

– BG

Industry Updates

Yahoo introduces Google-style image caching in email (UPDATE: confirmed with more details)

Geocache Cache Small Geocaching Logbook In late 2013, Google began to cache all images in email sent to Gmail users, storing remotely-hosted images on their own servers instead of accessing them each time an email is opened. Laura at Word to the Wise wrote up some good info at the time, focusing mainly on the parts of email tracking that were (or were not) affected by the changes.

Fast forward to 2018, and it looks like Yahoo has adopted a similar policy of image caching. According to Litmus, Yahoo recently began caching images on their servers in the same manner as Google. And like Google’s version, this one won’t break open tracking –  but could cause some unusual data points or issues with geolocation or user agent tracking. If you track the location of email opens, you’re likely to start seeing a lot more traffic from Sunnyvale, CA (the location of Yahoo’s servers), and any dynamically-generated content based on the location of the recipient will reflect that. In fairness, IP geolocation has never been a precise science, so most marketers should rely on other signals along with that data to serve up location-specific content.

When Google introduced this feature, they used it as a platform to allow images to load by default for all mail sent to the Inbox. There has been no announcement or indication thus far, but Is it possible Yahoo is planning a similar feature? As with most of the changes taking place under the new Oath umbrella; we’ll just have to wait and see. Yes, according to the answers provided by the Yahoo Engineering blog.

This morning, they officially announced the change, also confirming images will now be on by default for Yahoo and AOL in desktop and mobile versions. We can likely presume this applies only to messages in the inbox, though no specifics are provided. The post also indicates that Yahoo will “continue to support most” open tracking via pixel, though again details are sparse.

And for those using IP geolocation to serve dynamic content, the authors “recommend falling back on other tools and technologies which do not rely on IP-based targeting.” I won’t say I told you so.

– BG

Industry Updates

AOL mail seeing Yahoo deferrals as mail integration continues

170403180613-yahoo-aol-oath-780x439A few weeks ago we told you about AOL’s migration of their MX servers to Yahoo’s infrastructure as part of the merger of the two entities under Verizon’s new Oath brand. Since that change in early February, mail to AOL recipients has been handled by Yahoo’s servers. No specifics have been released on how the combined mail system will handle filtering, but observations of recent bounces may shed some light on that.

Over the past 2-3 weeks a number of senders have been seeing the dreaded “Yahoo deferrals” from recipients with AOL email addresses. These deferrals – temporary bounces usually caused by a high complaint rate – occur frequently for many high-volume senders mailing Yahoo recipients. These bounces are typically returned in a format similar to the following:

421 4.7.0 [XXXX] Messages from XX.XX.XX.XX temporarily deferred due to user complaints – X.X.X.X; see https://help.yahoo.com/kb/postmaster/SLN3434.html

The appearance of these types of bounces when sending to AOL recipients means you now have to contend not only with AOL’s spam filtering but with that of Yahoo. While AOL is known for its useful resources and responsive Postmaster team, the Yahoo Mail team can be more difficult to reach when issues arise. If you do run into any of these bounces, it’s probably a good idea to reach out to Yahoo via their Support form since the filtering is occurring on their mail servers.

– BG

Industry Updates

AOL confirms move to shared mail infrastructure with Yahoo

Last week I wrote about the changes taking place at major email providers, specifically the convergence of AOL and Yahoo’s mail servers. Today on their Postmaster blog, AOL issued confirmation of these changes. The statement indicates the “majority of AOL’s MX records” will be routed to the new combined mail servers with little if any visible impact to senders.

The message also assured senders that established feedback loops (FBLs) should continue to function without interruption. While AOL notes that issues are unlikely, if you see any abnormalities postmaster@aol.com remains the best way to reach out for assistance.

– BG

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

Industry Updates, Privacy & Security

500 million Yahoo users compromised in “worst hack in history”

tumblr_inline_nww8j3j32c1tnywua_1280On Thursday, Yahoo issued a statement confirming that at least 500 million users’ account data had been compromised in late 2014, supposedly by a “state sponsored actor,” or an individual hired by some governmental body to carry out the hack.

According to the statement, the data “may have included names, email addresses, telephone numbers, dates of birth, hashed passwords …and, in some cases, encrypted or unencrypted security questions and answers.” Yahoo indicates no financial data was breached.

Users who had or used Yahoo services, including Mail, Flickr, Fantasy Sports, and others, during that timeframe are being advised to change their passwords for Yahoo and any other services that may use the same login credentials, as well as changing security questions for other services.

Lots of questions surround this breach, with one of the most notable being why Yahoo waited so long to announce the hack. Many speculate information was concealed to prevent souring the sale of Yahoo to Verizon. CNN reports that Verizon learned of the hack for the first time this week.

As email senders and recipients, most of us care much less about Yahoo and Verizon’s financials than about potential fallout from the breach including identify theft, spam email, and even blackmail. Even if credit card data wasn’t stolen, the hackers now have personal information about millions of Yahoo users, including answers to some of the questions most commonly used to verify their identity.

Yahoo’s wait to announce the hack could mean the greatest damage has already been done: hackers often act quickly with stolen data, selling or sharing it quickly to outrun detection attempts. However, if the breach truly was initiated by a foreign government, the motivation may not be so clear.

Yahoo has said they are cooperating with Federal authorities to investigate, and it’s a safe bet we’ll hear more details as the investigation continues.

– BG