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MailMarketer’s Field Guide
to Gmail, Outlook.com, and Yahoo!
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Thanks to better ways to filter and block spam, inboxes are nearly free of unwanted
mail, but not without a price. According to past Return Path studies, permissioned
based email never reaches its intended destination — your customers’ inboxes —
about 20% of the time.
Email deliverability today is driven by content and reputation filtering. While it
would be great if there was a single algorithm that all of the mailbox providers used,
there isn’t. Gmail, Outlook.com, and Yahoo! Mail all have their own unique spam
filtering rules and services to help senders. Our field guide aims to help businesses
overcome confusion from the different rules of deliverability, or those who are just
strapped for time.
Introduction
Introduction
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Gmail
Gmail by the Numbers
Launched: 2004
Active Users as of 2012: 425 Million
U.S. mobile users using the Gmail app: 44.3%*
How many days prior to Gmail’s launch it took to design
the Gmail logo: 1
Number of email addresses that can be created by adding
a + symbol in front of the email address: ∞
The year Gmail purchased the domain Gmail.com from
Garfield.com: 2005
Unlike many of its large competitors, Gmail doesn’t provide
feedback loops, whitelists, disclose use of public blacklists or
provide a lot of direction, tools or support for senders. Don’t worry
about the lack of information Gmail provides. We’re here to help.
How Google Works - The Story of Send
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*(August 2013 U.S. Smartphone Subscriber Market Share - comScore, Inc)
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Gmail, like many major mailbox providers, primarily uses its
community of users to determine whether email is spam or not.
Gmail considers the following user feedback important in their
spam filtering decisions:
1. Report spam
2. Not spam
3. Messages Read
4. Messages Read and Deleted
5. Starred messages
6. Messages replied to
7. Inbox Activity
Content
As with most spam filters, the content of the email headers, body
and attachments are also scoured for keywords, images, HTML,
URLs, malware and many other common components. Content is
always tied and added to the overall spam filtering algorithm, but
how much weight it carries usually depends on the reputation of
the sender.
How Gmail Filters SpamSending History
Gmail temporarily blocks new IP addresses without a reputation for
the first 2 – 24 hours, then delivers small amounts of mail to both
the inbox and the spam folders to gauge subscriber perceptions.
If complaints are too high, future emails will be delivered mostly
to spam. If more people click on “not spam” during this period, this
indicates that the mail is safe to be delivered to the inbox.
Engagement
The number of active Gmail users may influence your reputation,
and therefore your inbox placement. A look at top brands and
the percent of their subscribers that are engaged – showing any
activity regardless if its negative or positive – shows a strong
correlation.
Chart: Brands with higher percentages of active users are more
likely to receive inbox placement.
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Blacklists
None.
However, our research shows a correlation between spam filtering
at Gmail and Spamhaus.
Enterprise Filters
As an aside, it’s important to understand that although Google
owns both Gmail and Postini products, each service utilizes its own
unique proprietary filtering technology. Google Postini Services
is a B2B spam filtering solution used primarily by corporations to
manage their enterprise mail. However, Google is switching current
subscribers of Google Postini services to Google Apps by the end
of 2013.
If you find your mail getting stuck in Google Postini Services’ spam
filter, Google does provide a Message Analyzer that allows senders
to examine the tags inserted into an email header to help decipher
the reasons for the quarantine. You may find a hint of the issues
with this tool but the only way to figure out how to get through
this filter is to constantly test different email content.
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When it comes to having a proper email set up, Gmail’s advises:
1. Consistently send from the same IP address(es)
2. Have valid rDNS for sending IP addresses pointing to your
domain
3. Use the same “From:” domain based on the type of email
4. Authenticate sending domains with DKIM and SPF
More on Authentication
SPF and DKIM authentication should be implemented. Be sure that
your From: domain matches the d= in your DKIM record. Senders
using shared IPs at ESPs should sign DKIM with their own unique
signing domain. For example, one should be signing mail with
something like d=esp.client.com instead of d=esp.com. If for some
reason you are not authenticating then Gmail creates a “best-
guess” record using a combination of record lookups to match your
sending IP with your domain to authenticate your email.
Partners
None.
Gmail does have thousands of hosted business domains that are
using Google Apps.
Mail Infrastructure
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1. Gmail Bulk Sender Guidelines
Gmail advises the best way to reach the inbox is by complying
with their Bulk Sender Guidelines:
• Publish an SPF record and sign with DKIM
• Get Permission
• Have an Unsubscribe link prominent
• “Not Spam” clicks – tells Gmail the messages are solicited
• Like with like – use different email address, domain, and IP for
different types of mail, like promotional and transactional
Senders can submit messages continually delivered to spam,
despite following and exceeding best practices, for review on
their Bulk Sender Contact Form.
Postmaster Services2. Feedback Loop
Gmail does not offer a feedback loop service in the traditional
sense. For senders using the list-unsubscribe header, whenever
an email is marked as spam, the subscriber will be asked if
they want to mark the email as spam and/or also unsubscribe
from future mailings. To prevent abuse of this feature, the
unsubscribe feature will only work for senders with good
reputations in the Gmail network.
In enable this functionality, the following are required:
• The email messages have a list-unsubscribe header which
points to an email address or an URL that a subscriber can easily
unsubscribe
• Sending domains publish an SPF authentication record, sign
outgoing email with DKIM, and pass at least one authentication
protocol
• The sender has a good reputation within the Gmail system.
Go to Gmail’s Bulk Sender Guidelines for more information,
or verify your reputation at SenderScore.org, where inbox
placement at Gmail and one’s Sender Score are highly
correlated.
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What is list-unsubscribe?
Josh Baer (Chief Innovation Officer and founder of OtherIn-
box, a Return Path company), and his friend Grant Neufeld
created the list-unsubscribe mechanism in 1998 while still
in college. RFC 2369 details the technical specifications of
the header, but the concept is simple – add a unsubscribe
mechanism in the email header and email providers can
offer better unsubscribe functionality than the link buried
in the footer of most emails that are required by the United
State’s federal law, CAN-SPAM, as well as other internai-
tonal laws regulating email and spam. Josh Baer also has
a website devoted to list-unsubscribe that includes the
specification and the participating mailbox providers that
use it.
Unsubscribe Methods
Besides reporting email as spam, Gmail users can access the list-
unsubscribe functionality by showing message details.
Show Message Details
To see the list-unsubscribe link, the recipient needs to expand the
message details by clicking on the small arrow next to where it says
“<<Sender>> to me.” This arrow brings down a message details list
and the “Unsubscribe from this sender” hyperlink will appear at the
bottom.
After the hyperlink is clicked, the following is displayed:
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Report Spam and Unsubscribe
This method will trigger a spam complaint, as it’s tied to the Report
Spam functionality. The sender will also receive an unsubscribe
notification, as shown above.
Regardless of the method selected, Gmail will send the following
unsubscribe request:
Whitelists and Prioritized Delivery.
Gmail does not offer their own whitelisting services nor do they
subscribe to any third-party whitelists.
Webmail providers have long been offering ways to deal with
one’s inbox, and one of the drivers behind this is the emergence of
what’s called graymail. Graymail lies somewhere between essential
emails and legitimate spam. Classifying emails as spam is in the
eye of the beholder most of the time and is rarely black and white,
hence the term “gray” mail. Graymail is essentially the overwhelm-
ing number of newsletters, coupons and advertisements that have
been legitimately opted in for, but are non-essential, and over time
can be difficult, or just downright annoying, to manage on a day-
to-day basis.
Gmail Priority Inbox
The Gmail Priority Inbox feature was launched in September 2010
and uses predictive analytics, as well as manual feedback, to iden-
tify and prioritize important email. Gmail predicts if a message is
important by examining how messages were treated in the past,
such as read or deleted and not read or manually marked as im-
portant, how the message is addressed to the recipient, and many
other factors.
Gmail’s Inboxes
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User Interface FeaturesGmail Classic How to “Mark as important”
How to “star” a message
Priority Inbox enabled
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A starred promotional message will appear in the Primary Inbox.
While the tabbed inbox is now default, Priority Inbox is still an option for Gmail users.
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Gmail’s Tabbed Inbox and Category Labels
In May of 2013, Gmail further innovated the inbox by releasing a
new email productivity feature based on inbox tabs and category
labels. Gmail’s tabbed inbox is now the default view for new Gmail
accounts, and has been enabled for most existing Gmail users.
Although, Gmail users have the option of turning the tabs off.
There are five labels total that are then categorized into their
corresponding tab within the inbox. Three of the tabs are on
by default (Primary, Social and Promotions), as well as two tabs
that can be turned on manually (Forums and Updates). Gmail
labels these emails using a special algorithm that looks at
everything from content, metadata and user feedback. Most of the
categorizations rules came from Smart Labels, a Gmail Labs project
that was released in March of 2011 that aimed to automatically
label and sort incoming mail.
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• Primary - person-to-person conversations and messages that
don’t appear in other tabs
• Social – messages from social networks, media-sharing sites,
online dating services, and other social websites
• Promotions – deals, offers and most other marketing emails
• Updates – personal, auto-generated updates including
confirmations, bills, receipts, and statements
• Forums – messages from online groups, discussion boards and
mailing lists
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1. Right-clicking and selecting the desired tab from the
“Move to tab” menu
2. Starring a message. The starred message will appear in the pri-
mary Inbox, but only that particular message will appear in the
primary inbox. Future promotional messages will still be filtered
to the Promotions, Social, Updates, or Forums tab.
Gmail users have the ability to influence how messages are
labeled by:
3. Dragging and dropping a message into the primary folder.
When a user drags and drops a message into a different tab,
Gmail prompts users if they would like all future messages from
that sender to go to the selected tab. If yes is selected, all mes-
sages from that sender will automatically be sent to the primary
folder going forward. However, if the Gmail user selects no,
messages from that sender will continue to go to the original
tab. Below is a campaign from Moosejaw asking their subscrib-
ers to move them to the Primary tab. G M
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4. Selecting the message and choosing a label from the Label
Dropdown. If a Gmail user has Priority Inbox enabled, tabs are
not displayed. However, the message labels show up in the
category views in the side bar. These messages will still appear
in the main inbox, and users can click on the category label to
view all messages with that particular label.
If a Gmail user has Priority Inbox enabled, tabs are not displayed.
However, the message labels show up in the category views in the
side bar. These messages will still appear in the main inbox, and
users can click on the category label to view all messages with that
particular label.
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Email Field Guide Page 13
Launched in 1996, Hotmail was one of the first web-based
email services. In fact, the name Hotmail is a play off of HTML, or
HoTMaiL. Its popularity now spans the world. Hotmail is one of
the most popular domains in the world, anddominates markets
in Brazil, Australia and most European countries. Microsoft has
established offices throughout the world to support its email
infrastructure, providing them with the insight needed to tailor
their tools and services to a diverse set of global users.
In 2013, Microsoft made a bold move and rebranded Hotmail and
Windows Live Mail to Outlook.com, a sign that consumer and
enterprise offerings are converging into the cloud.
Microsoft by the Numbers
Active Users: 400 Million
Emails received per day: 8 Billion
Of those received emails that reach the inbox: 30% - 35%
Domains: Outlook.com, Hotmail.com, Live.com, MSN.com
Hotmail Then (1996)
Hotmail (Outlook.com) Now
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SmartScreen
Outlook.com utilizes Microsoft’s patented SmartScreen anti-
spam filtering technology. This technology uses a machine-
learning approach to help protect users’ inboxes from junk email.
SmartScreen technology learns from known spam and phishing
threats as well as from Outlook.com’s customers who have chosen
to participate in the Feedback Loop Program (FBL).
Sender Reputation Data
Like many ISPs, Outlook.com considers volume, spam complaints
and spam traps into their filtering. However, the company places
a significant proportion of their filtering decisions from data in
their Sender Reputation Data (SRD) network, which Microsoft
refers to as the Spamfighter Club. Along with other sources of
reputation data such as the Junk eMail Reporting Program (JMRP),
SRD helps to train and improve the way SmartScreen technology
classifies messages based on email content and sender reputation.
Participants in the SRD program are selected from active
Outlook.com users at random from over 200 countries and no one
can volunteer for the program. Their votes on whether or not they
think your email looks spammy holds a lot of weight in filtering.
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1. Smart Network Data Services (SNDS)
SNDS is a free service that provides data on email volume,
subscriber complaints, spam traps, and more.
SNDS uses a color coded system which indicates trustworthiness:
Green indicates a positive sending reputation, and higher inbox
placement rates to Outlook.com are likely.
Yellow signals reputation issues starting to surface, and a mix of
inbox and junk folder placement is likely.
Red means that there are serious underlying reputation issues,
which are preventing most, if not all, emails sent to land in the
junk folder.
Postmaster Services
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2. Junk Mail Reporting Program (JMRP)
Microsoft offers their Junk eMail Reporting Program (JMRP) as
a free feedback loop (FBL) service to anyone who wants to sign
up. These FBLs are the result of spam complaints originating
from Outlook.com users only, and does not include SRD
participants. To improve one’s sending reputation, complainers
should be removed from your lists immediately. The headers of
the received FBL complaint will also indicate if the subscriber
marked it as junk or phishing. Emails marked as phishing
indicates that the sending identity wasn’t known, or perhaps
something in the content looked suspicious.
3. Support
Microsoft offers self-help and escalation paths for senders
having deliverability issues. Senders are asked to ensure
they are following all best practices on the Outlook.com
troubleshooting page. If senders are certain they are following
best practices, they can enter a ticket to the postmaster team.
Outlook.com Self-help
Outlook.com Support Ticket:
Like Gmail, Outlook.com also takes advantage of the list-unsubscribe header. There are two ways subscribers access the List-Unsubscribe functionality – through the “too many newsletters” footer or the “sweep” feature.
Too many newsletters? Unsubscribe.
As shown below, Outlook.com displays the “Too many newsletters?”
verbiage under the email. It is important to note that this verbiage
is not part of the email. Rather, it’s part of Outlook.com’s user
interface. When the hyperlink is clicked, the following pop-up will
be displayed if a List-Unsubscribe header is present.
Unsubscribe Methods
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Outlook.com
If the List-Unsubscribe header is not included, the following pop-up will be displayed:
Sweep Unsubscribe
Using Outlook.com’s Sweep feature, users can choose to
unsubscribe from the mail in question.
Either method of unsubscribing, the user will see a screen like this
where they can click a button to confirm the unsubscribe.
Microsoft does not maintain an internal proprietary whitelist. They
do however participate in Return Path’s Certification Program.
Participants in this program will bypass all spam filters and have
their email delivered to Outlook.com users with
images on.
Prioritized Delivery
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Outlook.com
Microsoft asks that senders’ mail infrastructure comply with the
following:
1. Sender ID and SPF – Microsoft asks all senders publish an SPF
or Sender ID record for the PRA domain.
2. DKIM - Microsoft also conducts DomainKeys Identified Mail
(DKIM) checks on inbound email. DKIM will be checked if
Sender ID fails. If both authentication methods fail then their
filters will make a decision to bulk the email or drop it all
together.
3. DNS – Microsoft requires a valid reverse DNS with a Fully
Qualified Domain Name (FQDN). If Microsoft webmail domains
are unreachable, Microsoft recommends querying the most
current list of MTAs through nslookup: “nslookup –q=mx
hotmail.com”
Mail Infrastructure
Microsoft has only one known partner that uses its infrastructure
and that is Sympatico (Bell Canada).
Outlook.com Inbox and User Interface
Partners
User Interface Features
The Outlook.com interface makes it easy to sort through personal mail, social
notifications, graymail, and more.
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Message featuresScheduled Cleanup Categorization
Outlook.com
Scheduled cleanup allows users to set rules to automatically delete old emails,
and only keep the latest from a sender. For most businesses sending email, this
isn’t an issue. For senders that send multiple times a day, have different From:
addresses for each mail stream may be needed.
Outlook.com’s categorization can be used as Quick Views for users, which is a
similar concept to Gmail’s tabbed inbox. The big difference is that Outlook.com
allows categories to be customizable.
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Archive Delete All From
Outlook.comOutlook.com’s Archive feature is similar to Gmail’s, but moves all messages to the
Archive folder keeping the main inbox clutter free.
The “delete all from” functionality allows users to easily delete all email from a
particular sender based on the From: address. This is good news for any business
that has had to deal with Hotmail users using the “Report Junk” button in the
past.
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Yahoo Mail
Yahoo MailYahoo! Mail was one of the first free webmail providers to hit the
market and is one of the three largest providers in the world with
281 million users. If smaller providers are included that utilize the
Yahoo! infrastructure, such as AT&T and BellSouth, Yahoo!’s mail
service covers 320+ million users globally. Yahoo! also re-designed
its email client in October of 2013 to make it more responsive and
better optimized for mobile devices.
Yahoo by the Numbers
Number of WorldWide users: 281 Million
Number of WorldWide users including hosted
infrastructure: 320+ Million
Number of active mobile users: 300+ Million
How much more Yahoo! users spend on electricity
compared to Gmail users: $110
How much Yahoo! spent to purchase Four11 for the
Rocketmail webmail service, which soon after became
Yahoo! Mail: $96 Million
Enjoy the view with Yahoo! Mail
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Yahoo Mail
Yahoo! builds the majority of their spam algorithms in-house.
They put a heavy emphasis on content, URL filtering and spam
complaints from its users. They are one of the few mailbox
providers that filter email by domain versus only IP address.
Reputation
Your reputation is critical in determining inbox or bulk folder
placement and is driven by many factors including unknown
user rates, spam complaints and known bad addresses or spam
traps. You should know that a sender’s reputation is made up of a
combination of IP Address +
Domain + From Email Address so it’s important that you maintain
consistency in all three of these components since changing any
one of these may lower your reputation and degrade your ability to
get to the inbox.
Engagement
Engagement has always been an important measure of subscriber
interest for senders, but mailbox providers are starting to make
significant investments in research, in-house spam filters and
third-party software to help measure subscriber engagement to
better determine appropriate folder placement. Factors being
considered include what messages are opened, what messages are
moved between folders and how quickly mail is deleted. So what
can you do about this? Get back to basics. Send relevant email that
your subscribers want by tracking opens, clicks and conversions.
If you have a large number of subscribers that have never opened
or engaged with your mail then it’s time to take a second look at
those addresses and determine if you can win them back or let
them go. Inactive subscribers will ultimately hurt your ability to get
delivered at all mailbox providers.
How Yahoo! Filters Spam
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Postmaster Services1. Best practices for bulk mail senders and postmasters for
sending to Yahoo Mail
Yahoo! tells senders the best way to get delivered to the inbox
is to avoid looking like a spammer. Start here to troubleshoot
Yahoo! delivery issues.
2. Troubleshooting SMTP Errors
If you’re mail isn’t getting delivered to Yahoo!, senders should
refer to their SMTP logs. Once the bounce code is discovered,
review Yahoo!’s list of common SMTP errors for the reason of
the error.
3. Yahoo! Complaint Feedback Loop
Yahoo! offers a complaint feedback loop service that is hosted
by Return Path. We recommend that you suppress that user
immediately from future mailings to maintain a positive
reputation with Yahoo!. Note that DomainKeys or DKIM
authentication is a requirement to sign up for FBLs.
Yahoo’s Whitelisting Options
There are 2 kinds of priority listings: Internal whitelisting and Re-
turn Path Certification.
1. Yahoo! Internal Whitelist: Yahoo!’s own whitelist is free, and
business’ can sign up for Yahoo!’s whitelisting service here.
Although it’s a whitelist, brands that are whitelisted are still
subject to certain filters, including user level filtering, content
filtering, and URL filtering. While the exact criteria to be ac-
cepted into Yahoo!’s whitelist isn’t public, they do require a posi-
tive sending reputation. Mailing from a new IP address, such
as moving to a new Email Service Provider or adding new IP
addresses, will require at least 30 days of reputation before
Yahoo! will consider whitelisting.
2. Return Path Certification: Yahoo! also honors the Return Path
Certification accreditation program. Return Path Certification
also acts as a whitelist, but allows accredited senders to bypass
certain filters to reach the inbox. Those accepted into the ac-
creditation program are required to maintain the standards set
by Return Path and its participating partners. More information
on the Return Path Certification program can be found here.
Yahoo Mail
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Mail Infrastructure 1. SPF, DKIM, and DMARC: Authenticating email with SPF and
DKIM is recommended. Yahoo! supports DMARC and the
standards that are required.
2. Connection and Throughput: Servers should be configured
to allow for simultaneous connections with throughput set
at 20 emails per connection. Rate limiting will occur for high
complaints and poor reputation, so use this as a guideline to
determine what the optimal setting for you should be.
3. rDNS: publish a PTR for your sending IPs, and use a Fully
Qualified Domain Name (FQDN) so it doesn’t look like a
dynamically assigned IP is sending mail.
4. Use a Consistent and Static “From:” address: Changing domains
and sending addresses will benefit senders in which their
subscribers whitelist their mailing address. It will also help
prevent email campaigns being identified as spam by Yahoo!’s
spam filters.
Yahoo! has several partners including AT&T (which includes
BellSouth, SBC and Ameritech), Verizon, Rogers, BT, TNZ, ExtraNZ,
and Nokia, who utilize Yahoo!’s infrastructure for its customers’
email. Each of these partners has their own filtering at their
gateways before it gets handed over to be processed by Yahoo!’s
filters, but we have found email sent to these partners should have
inbox placements rates that are consistent with direct Yahoo! users.
Partners
Yahoo! User Interface
Yahoo Mail
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returnpath.com
About Return PathReturn Path is the worldwide leader in email intelligence. We analyze more data about email than anyone else in the world and use that data to power products that ensure that only emails people want and expect reach the inbox. Our industry-leading email intelligence solutions utilize the world’s most comprehensive set of data to maximize the performance and accountability of email, build trust across the entire email ecosystem and protect users from spam and other abuse. We help businesses build better relationships with their customers and improve their email ROI; and we help ISPs and other mailbox providers enhance network performance and drive customer retention. Information about Return Path can be found at:
USA (Corporate Headquarters) [email protected]
Australia [email protected]
Brazil [email protected]
Canada
France [email protected]
Germany
United Kingdom [email protected]