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How to deliver into Outlook


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.


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 The (1996)

Hotmail (Outlook.com) Now


Spam Filtering

Outlook.com utilizes Microsoft’s patented SmartScreen antispam filtering technology. This technology uses a machinelearning 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.

Postmaster Services

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.
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 (https://support.live.com/eform.aspx?productKey=edfsmsbl3&ct=eformts&scrx=1)
Outlook.com Support Ticket: (https://support.live.com/eform.aspx?productKey=edfsmsbl3&ct=eformts&scrx=1)

Unsubscribe Methods

Like Gmail, Outlook.com also takes advantage of the listunsubscribe 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 d
displayed if a List-Unsubscribe header is present.

Mail Infrastructure

Microsoft asks that senders’ mail infrastructure comply with the
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”


Microsoft has only one known partner that uses its infrastructure and that is Sympatico (Bell Canada).

User Interface Features

Outlook.com Inbox and User Interface

The Outlook.com interface makes it easy to sort through personal mail, social notifications, graymail, and more.

Message features

Scheduled Cleanup
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.
Outlook.com’s Archive feature is similar to Gmail’s, but moves all messages to the Archive folder keeping the main inbox clutter free.
Delete All From
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.


Article refered from Marketer's Field Guide, ReturnPath 2013

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