Technical Brief
Protect Data in Motion with
Seamless Email Encryption
March 2010
NEED FOR EMAIL ENCRYPTION AT ITS PEAK
Because email has become the most prevalent tool for communication and collaboration by businesses and
government, it has never been more vital to protect the flow of confidential private and company
information transmitted via this medium. In the millions of messages sent weekly, content (including
attachments) inevitably contains data that is private. In every organization, HR, finance, legal, executives,
and other critical functions send email that is confidential at a minimum.
Based on the growing volumes of confidential and sensitive information traversing networks on a daily
basis, regulatory bodies and business executives have turned their concerns to ensuring messaging is
protected from unauthorized viewing. Regulations such as Sarbanes-Oxley, PCI, HIPAA, GLBA and others
have been introduced to mandate that email messages containing sensitive or confidential data are
handled securely.
With the increasing reliance on email, email encryption has emerged as a vital aspect of an overall email
security solution to secure confidential data and yet continue to allow the free flow of email
communications between colleagues, customers, and partners.
THE SOLUTION: SEAMLESS EMAIL ENCRYPTION FROM WATCHGUARD®
WatchGuard Email Encryption technology, powered by Cisco, provides easy-to-use, business-class
encryption to enable organizations to securely transmit and receive private and sensitive information. The
WatchGuard Email Encryption solution is available with all WatchGuard XCS appliances, and is tightly
integrated to enable instant-on security for confidential, regulated, and business-prudent information. It is
an effective tool for organizations that require messaging security for privacy and compliance and yet also
seek a solution with business-class features of reliable read receipts, secure replying and forwarding,
message expiration, and message recalling.
The transparent nature of the WatchGuard Email Encryption solution lends to its ease of use. The
WatchGuard XCS Data Loss Prevention engine identifies outgoing messages that meet pre-defined policies
for confidentiality and automatically encrypt the messages with no special action required by the sender.
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Encrypted messages are sent as HTML attachments to ordinary email messages and are directly delivered to
the recipient who can decode and view the encrypted messages using any web browser. Users and
administrators are able to view the status of individual encrypted messages and monitor the effectiveness
of corporate confidentiality policies with features including detailed delivery, response tracking, and
comprehensive message activity reporting.
WatchGuard Email Encryption enables organizations to:

Secure Confidential Information. Outgoing messages containing sensitive information are
transparently encrypted, delivered to any mailbox, and are easy for recipients to decrypt and view.

Adhere to Privacy and Compliance Regulations. Sensitive messages are handled in compliance with
industry regulations including HIPAA, PCI, SOX, GLBA and others without any effort on the part of the
sender.

Enhance Control and Visibility. Features such as guaranteed read receipts, message locking, and
message expiration provide enterprise-class encryption.
THE WATCHGUARD EMAIL ENCRYPTION ARCHITECTURE
While en route from a sender to a recipient, an email message may pass through several waypoints and
even multiple company networks before reaching its intended destination. Each of those waypoints and
networks may have different security policies and settings. A single weak link along this path may
compromise the confidential information within a message and can potentially result in leakage of sensitive
information. The consequences could be detrimental, including:

Brand erosion

Loss of customer confidence

Financial repercussions

Public embarrassment if it makes the headlines
Encryption provides an extra layer of protection to ensure sensitive data is not seen by unwanted eyes.
WatchGuard Email Encryption delivers an easy-to-use secure envelope solution which can be implemented
for employees, customers, vendors, and other business partners. As shown in Figure 1 below, WatchGuard
Email Encryption is an instant-on feature of the WatchGuard XCS.
Figure 1: Instant-On Encryption
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All email sent from the organization passes through the WatchGuard XCS appliance Data Loss Prevention
engine, which scans the data and matches it against pre-defined company and regulatory policies. Each
message then undergoes remediation whereby it is checked to determine if it needs to be encrypted,
quarantined, bounced, or handled in other ways as set by the policies set up by the Administrator, as shown
in Figure 2 below.
Once undergoing content filtering
inspection, if content or an attachment of
a message matches a policy which has
been specified for encryption, the
WatchGuard XCS processes the outbound
email and encrypts the message locally.
The key used to encrypt the message is
stored by Cisco Registered Envelope
Service (CRES), while the message is
queued for outbound delivery.
Figure 2: Discovery, Remediation and Inspection of Outgoing
Messages
Recipients of encrypted messages using
the WatchGuard Email Encryption solution
do not require special software or
applications to open an encrypted email.
Encrypted messages can be opened with
any email program and any web browser
running on any operating system. The
process is quite simple: recipients open an
HTML email attachment, enter a
password, and view the secure message.
HOSTED KEYS SERVICE
WatchGuard Email Encryption uses the CRES hosted key service, thus enabling instant-on deployment and
reduced management and hardware costs typically associated with local key servers. CRES technology
provides the following benefits:

Accounts are instantaneously created and users automatically enrolled

User authentication and message key delivery

Message tracking

SecureReply capability for responding to encrypted messages
The CRES hosted key server only holds encryption keys and management information. It does not ever hold
actual email messages and hence offers significant security benefits over other encryption solutions that
host both messages and encryption keys on the same system.
FILTERS AND LEXICONS FOR COMPLIANCE & POLICY MANAGEMENT
WatchGuard Email Encryption pulls on the capabilities of the WatchGuard XCS compliance and policy
dictionaries or custom dictionaries created by the administrator, as well as policies that search the subject
headers and body text of email messages as well as attachments, assisting organizations to comply with
industry regulations including:

HIPAA (Health Insurance Portability and Accountability Act)

GLBA (Graham-Leach-Bliley Act)
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
SOX (Sarbanes-Oxley Act)

European Privacy Initiative

NASD 3010

USA PATRIOT Act

SEC Rule 17
WatchGuard pre-defined compliance and privacy lexicons, which include terms, phrases, and alpha-numeric
listings related to financial, health, and other private information assist enterprises to be compliant with
industry regulations and alleviate the burdens and time required to set manual policies to identify sensitive
information.
FEATURES FOR ENHANCED VISIBILITY & CONTROL
Email security professionals using WatchGuard Email Encryption can expect to benefit from the exception
control over business email, including:
Guaranteed read receipts. With traditional email, senders wishing to track read receipts must manually set
up a read receipt request for each email prior to pressing the send button. Then, the sender must rely on
the recipient to initiate a reply in order to receive a read receipt acknowledgment. WatchGuard Email
Encryption eliminates this cumbersome process, since recipients must retrieve a decryption key from the
system before they read its contents. As such, the system knows when the message has been read and
provides automatic acknowledgement that the message has been retrieved. On the flip side, senders can be
automatically notified by the system if an encrypted email has not been opened prior to expiry, alerting the
sender to follow up directly with the recipient on important unread messages.
Message Locking. Occasionally, senders mistakenly send an encrypted email which contains inaccurate
content, or is mistakenly sent to the wrong recipient, or quite simply contains information that needs to be
recalled for various business reasons. With WatchGuard Email Encryption, senders can reduce the
consequences of such an error by locking an encrypted message to prevent it from being viewed even after
it has been delivered to the recipient’s inbox.
Message expiration. Senders can set an expiration date for encrypted messages, after which they can no
longer be opened. This can be done at the time the message is being sent, or the message can be expired
manually at any time after the message has been delivered.
ENCRYPTION OPTIONS: WatchGuard Email Encryption vs. Public Keys & Secure Webmail
WatchGuard Email Encryption is a next-generation solution that uses CRES secure envelope technology. It
should not be confused with first-generation public key encryption solutions which require special software
and certificates, or second-generation secure webmail encryption technologies, which uses a web server in
the system to store encrypted email. Rather, WatchGuard Email Encryption uses a web browser to
authenticate users and display decrypted messages. Ultimately, this results in a more cost-effective, secure,
and efficient solution for securing email than public key or web-based systems. Key benefits of the
WatchGuard Email Encryption solution include:

No Remote Message Storage. Users need not be concerned about confidential messages being
stored on a remote system – the encrypted incoming messages are delivered directly to the
recipients’ inboxes.

No Message Storage on Hosted Key Server. The CRES hosted key server does not store messages.
Encrypted messages and their keys are only ever combined on the recipient’s computer. This results
in a significantly more secure approach than storing both messages and decryption keys on a local
server.
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
Unlimited Scalability. Since WatchGuard Email Encryption leverages existing mail servers, there is no
need to set up a new mail system. Costly scalability, bandwidth, deployment, and administration
costs are hence eliminated.

No HTTPS Access Enablement Required. WatchGuard Email Encryption does require inbound HTTPS
access to be enabled for encrypted email retrieval.
THE USER EXPERIENCE
WatchGuard Email Encryption has been specifically designed with ease-of-use at the forefront such that
employees, customers and other business partners can immediately appreciate the benefits associated with
encrypted email communications.
Sending Encrypted Email
Transparent Encryption
WatchGuard Email Encryption is transparent to employees. When sending an encrypted email, the user
simply composes and sends the email as he would at any other time. As shown in Figure 3 below, the
content of the outgoing email is then automatically scanned and, if deemed to contain sensitive material as
pre-defined by your organization’s policies, it is then automatically encrypted.
Figure 3: Transparent encryption based on pre-defined organizational policies
Manual Encryption
WatchGuard Email Encryption also allows a sender to clearly flag a message for encryption by adding the
word “Encrypt” in the subject line. This is then automatically identified by the system filter and the message
is encrypted before being sent.
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Extending Encryption to Customers and Partners
Once WatchGuard Email Encryption has been deployed internally, organizations can extend its benefits to
customers and business partners who may wish to communicate with them in a confidential manner.
WatchGuard Email Encryption allows secure communications between organizations and remote external
users without the need to set up secure mailboxes before new users can send encrypted messages. It is a
simple process. Links to WatchGuard Email Encryption can be added to an organization’s public website.
Those wishing to send secure communications merely click on the link and complete a simple registration
process, at which time WatchGuard Email Encryption launches a browser-based message form. All the
remote sender needs to do is then compose and send a message which is encrypted and forwarded to the
intended recipient.
Receiving Encrypted Email
As mentioned previously, no special software is required to receive and read encrypted messages with
WatchGuard Email Encryption. Recipients can open encrypted messages with any desktop email program or
any web browser running on any operating system.
When receiving an encrypted email using WatchGuard Email Encryption, the recipient receives a
notification message which arrives as a plain-text email with an HTML attachment. The notification
envelope can be fully customizable with the sending organization’s logo and branding, and supports both
HTML and text.
On opening the attachment, an envelope displays in the browser and asks the recipient for a password, as
shown in Figure 4 below. Integrated anti-phishing through a two-way Personal Security Phrase (chosen by
the user during account setup) enhances user confidence that the message is legitimate and has come from
a trusted source.
Figure 4: Recipient password-entry screen
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Those who are receiving encrypted emails for the first time are not required to set up an account in
advance of using the system. Rather, they are directed to a screen, as shown in Figure 5, to create an
account on CRES. The need for first-time user registration is automatically detected when no account exists
for the recipient’s email address. Once a recipient has set up an account on CRES, they can receive secure
messages from any number of senders and can also log into their account at anytime to compose new
encrypted messages.
Figure 5: First-time recipient registration
Once recipients have entered their passwords and the password has been successfully authenticated by
CRES, the decryption key is sent to the recipient’s system and the decrypted message is automatically
displayed in the browser window, as shown in Figure 6.
Figure 6: Decrypted message displayed in browser
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Once access to the decrypted message is obtained, the recipient has the ability to securely Reply, Reply All
(configurable), and Forward (configurable), without requiring any special software.
WatchGuard Email Encryption provides enhanced security to keep unwanted eyes from viewing the
document after it has been opened by requiring that the decryption key be retrieved from the server each
time the message is read, allowing message to be locked by the sender even after they have been read.
The Message Decoding Process
Messages are encrypted using either AES or RC4 (both highly secure) industry standard algorithms. The
HTML attachment in the notification contains the encrypted message content, as well as JavaScript to
decrypt it locally, thus eliminating the need to install special software and enabling the solution to have
universal reach with high usability.
In some cases, JavaScript is not always available. It may be stripped out at the receiving gateway or disabled
in the recipient’s browser. This does not hinder a recipient from easily decoding encrypted messages. CRES
technology performs the encryption over a link secured with the SSL protocol. Once the recipient enters his
or her valid password, the encrypted message is automatically posted to CRES for decryption. The
decrypted message is then sent back to the recipient’s browser for display. Although this method of
decrypting messages is slower and less scalable than decoding them locally, it is a viable alternative when
JavaScript is not available.
ENCRYPTED MESSAGE TRACKING AND REPORTING
WatchGuard Email Encryption’s web-based interface allows users and administrators to track messages and
run reports on encrypted message activity, including:
Delivery & Response Tracking
When an encrypted message is opened, notifications are sent to the server and read receipts can be
optionally generated for senders. Administrators can also configure time-based triggers to track when a
message is opened and to signal when they have not been opened within a specified period of time.
Message Activity Reporting
WatchGuard XCS provides extensive content filtering reporting capabilities. Administrators can generate
reports which indicate how many messages were flagged by each pre-defined policy and can also generate
reports by user, as well.
CONCLUSION
The WatchGuard Email Encryption solution is the most comprehensive and easy-to-use tool for keeping
confidential information secure and avoiding embarrassing and potentially damaging and costly data
leakage caused by user errors or oversights.
The WatchGuard Email Encryption solution provides maximum security to organizations and its users with
its transparent encryption capabilities using custom or pre-defined policies, data loss prevention, and
compliance dictionaries. Also, since messages are never stored on the same server as their keys, the
WatchGuard Email Encryption solution ensures that only those with permission to view the encrypted
message have access to its content.
Organizations concerned with compliance to both industry regulations and internal corporate policies can
confidently rely on WatchGuard Email Encryption in correlation with the WatchGuard XCS to scan outbound
messages with its powerful Data Loss Prevention and take the appropriate remediation, including blocking,
quarantining, or automatically encrypting messages containing confidential and sensitive information in
accordance with corporate policies. Using a policy-driven approach which can easily be extended and
customized to meet individual needs for controlling confidential data, the WatchGuard Email Encryption
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solution ensures that corporate rules and standards for sensitive information transmission are consistently
applied.
Providing even greater control over business email are features such guaranteed read receipts, message
locking, message expiration, and message tracking and reporting such that users and administrators have
visibility into the status of encrypted message transmission and receipt.
No other solution on the market provides greater flexibility and ease-of-use. With its transparent
application and universal reach, messages encrypted with WatchGuard Email Encryption can be sent to any
email inbox without requiring administrators to set up new users or needing on the part of the recipient to
install client software. Thus, confidential ad hoc communication with business partners and customers is
simplified and scalable.
It has never been easier to deploy encryption as part of an overall email security solution. WatchGuard
Email Encryption provides the necessary infrastructure so that all you have to do is enable it on the
WatchGuard XCS, set Data Loss Prevention policies and compliance rules, and your outgoing emails and
data will be protected from unintended viewers.
NEXT STEPS
For more information on the powerful WatchGuard XCS family of extensible content security products with
next-generation email encryption capabilities, visit www.watchguard.com/xcs.
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ABOUT WATCHGUARD
Since 1996, WatchGuard Technologies has provided reliable, easy to manage security appliances to
hundreds of thousands of businesses worldwide. WatchGuard’s award‐winning extensible threat
management (XTM) network security solutions combine firewall, VPN, and security services. The
extensible content security (XCS) appliances offer content security across email and web, as well as
data loss prevention. Both product lines help you meet regulatory compliance requirements including
PCI DSS, HIPAA, SOX and GLBA. More than 15,000 partners represent WatchGuard in 120 countries.
WatchGuard is headquartered in Seattle, Washington, with offices in North America, Latin America,
Europe, and Asia Pacific. For more information, please visit www.watchguard.com.
No express or implied warranties are provided for herein. All specifications are subject to change and
any expected future products, features, or functionality will be provided on an if and when available
basis. ©2010 WatchGuard Technologies, Inc. All rights reserved. WatchGuard, the WatchGuard Logo,
and WatchGuard ReputationAuthority are either registered trademarks or trademarks of
WatchGuard Technologies, Inc. in the United States and/or other countries. All other trademarks and
tradenames are the property of their respective owners. Part.No. WGCE66694_031610
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