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Page 1: Marketer’s Field Guide - DMNews.commedia.dmnews.com/documents/58/marketer's_field_guide_to...Share this: The Marketer’s Field Guide to Gmail, Outlook.com, and Yahoo! Introduction

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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-

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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.

Spam FilteringO

utlook.com

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]