Web security buyers guide

Web interactivity increasingly relies on user- and third-party-generated content built on rich backend database systems,
which are easily exploited. This has created a breeding ground for the distribution of malware—even among the most
trusted and popular web sites and applications. This dramatic change in the nature of web threats has rendered
traditional web filtering technology completely ineffective. Simply blocking access to sites that may host malware is no
longer a viable solution – as that would now include each and every site on the net.

With the web now a mission-critical tool in most organizations day-to-day activities, it’s critical to equip yourself with a
security solution that enables the users to be productive, while also providing the security essential to ensure a risk-free
experience.

Organizations looking for protection against modern web threats need a solution that demonstrates security attributes
that combines powerful application, site and content controls with proactive malware detection. In today’s economy,
best-of-breed security must also embrace low-impact, effective administration enabling organizations to do more with
less. At the same time, the solution must meet end-user expectations and requirements for speed, efficiency, and open
access to the tools and sites they need. Solutions which fail to meet these demands for security, control, performance,
value and accessibility will ultimately fail the organization.

Introduction
The web is now the number one vector of attack A new approach to web security and control is required that
for cybercriminals, with a newly infected web site fully supports the needs of businesses, equipping users with
discovered every few seconds. Hijacked trusted the tools they need to be more effective while eliminating
sites, poisoned search results, fake AV, and phishing the associated risks of potential infection from trusted
sites are all finding their way into our browsers at an legitimate sites. In addition to good preventive practices,
alarming rate. As a result, Internet access creates a such as rigorous patching and educating users about the
dilemma for you: on the one hand, the risks presented risks of browsing, it is vital that organizations implement a
by allowing unfettered access to the web are comprehensive web security and control solution.
enormous, yet the Internet is undeniably becoming a
mission-critical business tool. Social networking sites,
blogs, forums and media portals have all become
important instruments for employee recruitment, viral
marketing, public relations, customer interaction, and
research. They cannot be blocked without seriously
impacting business productivity and effectiveness.

Web security buyers guide

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Web security buyers guide

Web Security and Control Overview

Security and Control Components: Application Control

• Application control Web application control is not just about productivity –

• Productivity and reputation filtering
• Proxy filtering
• Real-time malware filtering
• HTTPS filtering
• Content-based filtering
• Data loss prevention
In addition to best-of-breed security, the solution must
also fit seamlessly into your organization.
Deployment, Management, and Vendor Capabilities:
• Low-impact end-user experience
• Flexible easy deployment
• Minimal administrative burden
• Intuitive management console
• Rich dashboard and reporting
• World-class vendor services and support
Finally, the solution must be affordable, providing
maximum value for your investment.
The rest of this document is dedicated to articulating the key
components of an effective web security and control solution.
it’s an important foundational layer to an effective web
protection strategy.
Most web malware utilizes commercially available exploit
packs that contain dozens of different vulnerability
testers, redirectors, and actual exploit code that attempt
to test for and exploit a myriad of vulnerabilities that
exist in applications on the user’s system. These kits are
designed specifically to prey on users who aren’t diligent
in keeping their software and operating system patches
up to date. It’s therefore critical to not only keep your
applications patched and up-to-date, but also minimize
and limit the number of web applications in your
environment to an absolute lowest common denominator
standard set of business related programs and tools.
Unfortunately, traditional application controls at the
gateway rely on port or packet inspection to identify
and control instant messaging, peer-to-peer and other
non-browser web applications. The problem with this
approach is that it doesn’t prevent these applications
from being installed and ultimately exploited. This is
where a security suite that integrates both endpoint and
web protection together can offer enormous benefits, by
controlling unwanted applications on the desktop, before
they can become exploited and infected.

Web security buyers guide 2

Web security buyers guide
URL and reputation filtering
Traditional URL filters rely on vast, regularly updated
databases of sites classified into different categories
for the purposes of controlling productivity and
enforcing acceptable use policy. URL filtering was once
considered an acceptable web security solution, but
the presence of web malware has shifted dramatically
from dodgy porn and gambling sites to much more
popular mainstream websites across all categories. So
while URL filtering plays an important role in optimizing
network performance and staff productivity by blocking
access to illegal, inappropriate, or non-business-critical
web content, it is not an effective security solution
against modern threats to hijacked trusted sites.
Reputation-based filters are designed to augment URL
filtering and act as the first critical component in the
fight against modern web-based threats. They prevent
access to a continuously growing catalog of sites across
all categories that are known to be currently infected
or have hosted malware or other unwanted content in
the past, by filtering URLs based on their reputation as
“good” or “bad.” Reputation filtering is now considered
a proven and essential tool for successfully protecting
against already known web-based threats across all site
categories.
Proxy filtering
Anonymizing proxies are specially designed sites that
enable users to browse blocked sites anonymously and
free of company web security filtering. Obviously, these
kinds of sites can completely undermine an effective
web security and control solution, exposing users and
the organization to significant security risks, legal liability
issues, and productivity losses.
Web security buyers guide
To prevent users from bypassing filtering controls, the
following two components are critical in forming a
defence against anonymizing proxy use:
• A reputation-based service that actively seeks
out new anonymizing proxies from a variety of
underground sources as they are published and
updates the filtering database at frequent, regular
intervals.
• A real-time proxy detection engine that automatically
inspects traffic for signs that it’s being routed through
a proxy, effectively closing the door on private home-
based proxies or other proxies not identified through
the reputation service.
Real-time malware filtering
Real-time predictive malware filtering goes a long way
toward closing the gap left by reputation-based filters.
With this kind of filter, all web traffic passes through
a scanner designed to identify both known and newly
emerging zero-day malware. The malware engine is
optimized for low-latency scanning. Whenever a user
accesses a website, regardless of its reputation or
category, the traffic is scanned using a combination of
signatures and behavior-based technologies.
It is worth noting that this type of real-time scanning
has a further advantage over traditional URL filters: the
filtering is, almost by definition, bi‑directional – both
the user request to and the information returning from
the web server are scanned. In addition to detecting
known malware as it moves across legitimate sites, this
bi-directional filtering can also provide protection against
new threats regardless of where they are hosted.
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Web security buyers guide
A real-time malware scanning engine is not only the most
critical component of an effective web security solution,
it is a key point of differentiation among vendors. As
a result, buyers should pay particular attention to the
capabilities of their web security solution short list, and
focus on some key considerations related to malware
scanning capabilities:
• Real-time: looks at content as it’s accessed or
downloaded
• Behavioral: goes beyond signatures to analyze code
for malicious intent before it executes
• Script emulation: will decode and emulate obfuscated
JavaScript before passing it to the browser
• Bi-directional: inspecting both outbound requests
and incoming content
• Multi-vector: provides integrated malware detection
across several vectors including the gateway, the
browser, and the desktop
• Low latency: can scale and handle peak loads
efficiently to ensure a seamless user experience
• Update frequency: signature and threat identity
information should be provided at intervals measured
in minutes, not hours or days
HTTPS filtering
With up to 40% of web applications and protected web
sites now relying on port 443 Secure Sockets Layer
(SSL), this is an increasingly popular vector for malware
distribution and therefore a critical component of an
effective web security solution. Since SSL content is
encrypted, it can’t be intercepted by most traditional web
security solutions, which leaves IT completely blind to
this traffic. It’s no surprise that most proxy sites, phish-
ing attacks, fake AV sites, and other malware attacks
increasingly utilize this highly vulnerable point of entry.
This major blind spot in security can also be a significant
liability for data leakage, unwanted downloads via web-
mail solutions like Gmail, and bandwidth consumption.
Web security buyers guide
HTTPS traffic inspection that enables a balance of
user privacy with organizational security is critical to
an effective web security and control solution. What’s
essential is a flexible solution that provides certificate
validation with legitimate sites like financial institutions,
while fully proxying and scanning other HTTPS sessions
for signs of malware, unwanted content, phishing
attacks, malware calling home, and proxy use.
Content-based filtering
Content-based filtering analyzes all web traffic on
the network to determine the true file type of content
coming back from a website. It can then allow or
disallow this traffic, based on corporate policy.
Content filters scan the actual content of a file, rather
than simply looking at the file extension or the MIME
type reported by the web server, and so can identify
and block files that are masquerading as innocent
or allowed file types but really contain unauthorized
content. A file might, for example, have a .TXT
extension but in fact be an executable file.
By enabling enforcement of only business-type content,
this pillar of protection enables organizations to create
policies around a variety of content types that are often
used to send malware, thereby dramatically reducing
the risks of infection. For example, incoming Windows
executables or screensavers might be disallowed.
Content-based filtering can also be used to improve
bandwidth optimization by blocking large or resource-
hungry content, such as streaming video.
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Web security buyers guide

Data loss prevention Key Buying Criteria

Data loss prevention is an increasingly important element The following table fully articulates the key buying
of an effective web security solution in the Web 2.0 world. criteria you should consider when evaluating a potential
With strict privacy and data confidentiality regulations and web security and control solution. Use this as a guide
requirements becoming common in most jurisdictions, for your online research, vendor discussions, or RFP. Be
it’s becoming critical to enforce a comprehensive data sure you are getting the most value for your investment
protection strategy that governs mobile computers, in web security and control by ensuring your vendor is
removable media, devices such as USB sticks, traditional providing you with a complete solution that is simple
email, and of course Web 2.0 applications. to deploy and administer, from a trusted source that
provides the service and support you require.
For a DLP engine to be effective, it must be able to
scan and recognize sensitive data types such as credit
card numbers, personally identifiable information,
bank account information, social insurance numbers,
and more. Predefined content control lists (CCL’s) that
cover hundreds of different sensitive data types across
multiple localized geographies are critical to making DLP
manageable and effective.

Furthermore, the most effective DLP will be that which

can cover all potential exit points including removable
media, devices, email, web and social media applications
and stop sensitive data from being exposed at the source –
right on the user’s desktop. It should also integrate tightly
with encryption solutions to facilitate the movement of
sensitive data that does need to leave the organization.

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Web security buyers guide
Security and Control Components:
Web application control:
Control and limit the number of
web applications in the environ-
ment to reduce the threat surface
area from exploits
URL filtering database:
Categorization of websites with
block/allow policy options
Web security buyers guide
What to look for: Look for an application control solution that runs on
the endpoint and can block unwanted applications at the source – on the
desktop. Solutions that simply inspect ports or packets at the gateway
are ineffective at controlling the risk of being exploited – stop these apps
from running in the first place. Also look for a solution which can identify
applications based on identity signatures rather than relying on common
path and file names to avoid masquerading apps from side-stepping
controls. Also ensure the solution enables easy control over categories of
applications with granular control as needed and provides regular updates
to the app control lists on a regular basis to make administration easy.
Specific questions to ask:
• Does your app control block applications from running on the desktop?
• Does your app control rely on signatures or file and path names?
• How many application identities does your solution include?
• How often is the database of apps updated?
• Do you support flexible, easy to use policies with app categories?
What to look for: While URL classification databases are largely a
commodity, select one that has categories that make sense for your
organization. More categories are not always better as it may create
added complexity for your policy management. Ensure multiple languages
are provided and the URL database is significant in scope and updated
regularly. Also ensure that policy controls are simple, wizard driven, and
enable policies set by user, group, time, site, or category with flexibility to
easily create custom policies.
Specific questions to ask:
• How many languages does your database cover?
• How often is the database updated?
• Who updates the database and what resources do they have/use?
• Are your policy settings wizard driven?
• Do you support custom policies with site tags and special hours?
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Web security buyers guide
Security and Control Components:
Reputation database:
Augments URL filtering with
reputation and risk classifica-
tion to ensure risky sites in any
category are scanned or blocked
Anonymizing proxy detection:
Blocks users from using proxies
to bypass web filtering
Web security buyers guide
What to look for: A reputation database that is maintained by a top-tier
security company that invests heavily in web malware research and provides
frequent updates. Also, look for a solution that protects both networked
corporate users as well as mobile or remote users who may not be operating
on the corporate network.
Specific questions to ask:
• Does your reputation database protect mobile and remote users outside
the office?
• Do you track site reputation across categories?
• How does your solution deal with risky sites within allowed categories?
• How often is the database updated?
• Who updates the database and what resources do they have/use?
What to look for: A combination of real-time proxy detection to identify
new or obscure proxies, coupled with a comprehensive proxy discovery
service to ensure policy compliance. Inquire about what sources your
web security vendor uses to catalog anonymizing proxies, how many they
catalog every day, and how often they provide updates. Avoid any solution
which cannot detect anonymizing proxy use in real-time as users initiate
a connection through one, as there are plenty of obscure or home-based
proxies that any reputation service will never find.
Specific questions to ask:
• How often do you update your catalog of anonymizing proxies?
• How many new anonymizing proxies do you detect daily?
• How does your solution handle obscure or private/home-based proxies?
• Who updates the proxy catalog and what resources do they have/use?
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Web security buyers guide
Security and Control Components:
Real-time malware scanning:
Scans all inbound and outbound
web traffic in real-time
Web security buyers guide
What to look for: Not all web malware scanning is created equal. Avoid
signature-based scanning engines and select an engine that utilizes
behavioral pre-execution analysis to determine code intent which will
provide zero-day protection from new malware. Furthermore, inquire about
obfuscated javascript. If the anti-malware engine cannot deobfuscate and
emulate javascript in real-time to analyze its behavior before passing it
to the browser, look for a solution that does for the best protection from
server side polymorphing malware. Since malware scanning is particularly
important, here’s an additional checklist of important criteria:
• Real-time: looks at content as it’s accessed or downloaded
• Behavioral: goes beyond signatures to analyze code for malicious intent
before it executes
• Script emulation: will decode and emulate obfuscated javascript before
passing it to the browser
• Multi-vector: provides integrated malware detection across several vectors
including the gateway, the browser, and the desktop
• Bi-directional: inspecting both outbound requests (for signs of malware on
your network calling home) and incoming content
• Low latency: can scale and handle peak loads efficiently to ensure a
seamless user experience
• Update frequency: signature and threat identity information should be
provided at intervals measured in minutes, not hours or days.
Specific questions to ask:
• Does your reputation database protect mobile and remote users outside the
office?
• Do you track site reputation across categories?
• How does your solution deal with risky sites within allowed categories?
• How often is the database updated?
• Who updates the database and what resources do they have/use?
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Web security buyers guide
Security and Control Components:
Call-home detection:
The ability to physically intercept
and analyze outbound traffic
through the gateway to identify
infected systems or sensitive
data leaving the organization
HTTPS scanning and
certificate validation:
The ability to proxy and scan
all web traffic including HTTPS
encrypted channels often used by
webmail, anonymizing proxies,
etc., which are increasingly being
targeted by malware
True file type control:
Examines all file downloads
to determine their true type to
dramatically reduce the threat
surface area from undesired
file types
Web security buyers guide
What to look for: A system that intercepts and scans outbound requests
as well as incoming web traffic. If your desired solution cannot scan
outbound web requests, there’s no way to prevent infected machines
on your network from sending sensitive data or even identifying what
machines on your network might be infected.
Specific questions to ask:
• Does your system scan and analyze outbound requests and web traffic?
• How does it identify machines that are potentially infected and calling home?
What to look for: A solution that can not only proxy and scan HTTPS
encrypted connections, but one that can balance the need for end-user
privacy with bank and financial institution exceptions. Also look for
certificate validation to avoid phishing attacks that spoof certificates to fool
users into believing they are secure.
Specific questions to ask:
• Does your solution enable the proxy and scanning of HTTPS encrypted traffic?
• Does it have the capability to exclude financial institutions?
• Does it perform certificate validation?
What to look for: A solution that simply looks at file extensions or MIME
types is inadequate. Only consider a solution that does true file type
detection by inspecting the file header information. This is the only way to
prevent content masquerading to reduce your threat surface area and keep
undesirable or illegal content off your network.
Specific questions to ask:
• How many file types does your solution identify and control?
• What technique does it use to identify files (extensions or header analysis)?
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Security and Control Components:
Data loss prevention:
Examines content for sensitive
data to prevent it leaving
the organization through
unauthorized means
Deployment, Management & Vendor Capabilities
Scalable:
A solution that scales with
your growing business, from
small companies to large,
geographically distributed
enterprises
Web security buyers guide
What to look for: A DLP solution should cover all vectors of potential data
loss including removable media, devices such as USB sticks, traditional
email, and Web 2.0 applications. Ideally the solution should block
sensitive data leaks at the source – on the user’s desktop. It must include
a predefined list of sensitive data type definitions and must be updated on
a regular basis as new sensitive data types are defined.
Specific questions to ask:
• What is the scope of coverage of your DLP solution?
• Where does it run and block sensitive data at?
• How many sensitive data type definitions are included?
• Can the sensitive data types be easily extended or customized?
• How often are the sensitive data types updated?
• Does the DLP solution integrate with encryption options for data that does
need to leave?
What to look for: A range of different hardware appliance models at
price points attractive to organizations of all sizes that enables you to
easily upgrade as your business grows. In particular, look for a solution
that offers simple centralized management of multiple appliances in either
a single site for performance and redundancy or across multiple sites for
geographically distributed organizations.
Specific questions to ask:
• What range of models do you offer?
• Do you offer an affordable solution for small businesses or small
branch-office locations?
• Do you offer centralized management for consistent and easy policy
settings across a large number of appliances?
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Web security buyers guide
Deployment, Management & Vendor Capabilities
Flexible deployment modes:
Different deployment options that
enable the solution to fit with
your IT and business objectives
providing the ideal balance
between security and ease-of-
deployment and management
Directory services integration:
The ability to integrate with your
Microsoft Active Directory or Novell
eDirectory services to identify and
authenticate users automatically
Easy to manage:
A solution that is immediately in-
tuitive and doesn’t consume a lot
of your time and effort to set up
and administer on a daily basis
Monitoring and alerting:
The health of the appliance or
solution is monitored remotely
and alerts are provided in the
event of any malfunction
Web security buyers guide
What to look for: The ideal solution will support a range of options including
explicit proxy mode, transparent mode operation, and support for Cisco’s
WCCP protocol. Avoid solutions that rely strictly on port-spanning operation.
Specific questions to ask:
• Does your solution support explicit proxy mode?
• Does your solution support Cisco’s WCCP protocol?
• Does your solution support transparent mode with directory service integration?
• How long does it take to deploy and configure your solution?
What to look for: Support for both Microsoft and Novell directory services
with easy setup and integration for user-based policy settings and reporting.
Specific questions to ask:
• Does your solution support Microsoft Active Directory integration?
• Does your solution support Novell eDirectory integration?
What to look for: If you can’t get the system deployed in just a few minutes
without a lot of documentation or several calls to your vendor’s support line,
then you have the wrong product. Select a solution with task-based, wizard-
driven setup, policy administration, and reporting. Avoid any solution that’s not
immediately clear and intuitive.
Specific questions to ask:
• What’s required to set up and configure the system?
• How intuitive is the management console?
• Does the setup and configuration use wizards, or lots of screens with fields
that are poorly labeled?
• Does the solution provide thorough online help?
• How many steps does it take to set up a typical policy?
What to look for: A solution that is remotely monitored for you by your
vendor that will alert you immediately if anything is wrong.
Specific questions to ask:
• Do you monitor the health of your solution for each customer?
• If so, do you provide alerts and remote remediation?
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Web security buyers guide
Deployment, Management & Vendor Capabilities
Dashboard and reporting:
The ability to monitor your user,
web traffic, and threat activity at
a glance from a real-time dash-
board, and drill down into rich
and sophisticated reporting for
forensics and compliance insight
Frequent updates:
Frequent updates to malware
identities, risky or malware-infested
sites, and anonymizing proxies
Web security buyers guide
What to look for: A solution that has an aggregate dashboard that
can span multiple separate appliances and present real-time status on
user activity, throughput, latency, threats, and other important Internet
traffic metrics. It’s more important that the reporting system provide the
information you need in a simple convenient manner than try to wow you
with the sheer number of different reporting options. Reporting should be
simple and provide drill-down capabilities, with a variety of important user,
traffic, and activity reports to satisfy all stakeholders in your organization.
Look for solutions that can provide both ad-hoc up to the minute reports
while also supporting a variety of parameters and export options including
PDF output. In addition, regular scheduled reporting is essential to save
you time and effort satisfying the needs of various stakeholders in the
organization... Beware: once you have rich Internet activity reporting at
your fingertips, everyone will want it.
Specific questions to ask:
• Does your solution offer centralized reporting across multiple appliances
and locations?
• Does your solution offer an aggregate real-time dashboard across multiple
appliances and locations?
• Does your solution offer up-to-the-minute ad-hoc reporting?
• Does your solution offer PDF output for easy sharing of reports?
• Does your solution offer regularly scheduled reports that are automatically
emailed to stakeholders and easy to set up with a simple wizard?
• Does your solution offer reports for network traffic, user activity, policy
warnings and violations, top offenders and more?
• What is the length of data retention for reporting?
What to look for: Ideally your solution should update as frequent as every
few minutes as needed. Avoid solutions whose update frequency is measured
in hours. By the time you get an update, it’s likely too late.
Specific questions to ask:
• How often do you provide threat updates?
• Who maintains the updates and what resources do they have/use?
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Deployment, Management & Vendor Capabilities
Easy upgrades:
Updates to product software are
easy to deploy
Service and Support:
The support experience
Security labs:
The team responsible for threat
analysis and security updates
Web security buyers guide
What to look for: Ideally your product should update automatically without
any intervention and at no extra cost for minor or major version releases.
Specific questions to ask:
• What’s required to install a software update to the system?
• How much do updates and upgrades cost?
What to look for: A company that treats you like a partner in protecting
your organization, and that offers 24/7/365 support at no additional cost
with immediate access to local front-line engineers who can actually
help in your language. Also look for a solution that offers an advance
replacement warranty on all hardware. Avoid vendors whose support is all
overseas or who deal with both enterprise and consumer customers.
Specific questions to ask:
• What support is included at no extra charge?
• When I call support, who am I talking to and where are they?
• Does your company support both corporate and consumer solutions?
• What premium support options do I have?
What to look for: Look for a solution backed by a top-tier global round-
the-clock security labs operation that deals with blended email, web, and
endpoint threats.
Specific questions to ask:
• How many people work in your labs operations?
• Where are they located?
• Do team members specialize in certain threats or are the labs’s research
fully blended across spam, web infections, and viruses?
• What level of automation and other resources do they utilize to keep
ahead of the threats?
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Buying Guide Checklist

Criteria Sophos Other

Security and Control

Web Application Control
• Desktop control over applications  –
• Uses Application Identities  –
• Granular policy control  –
• Frequent identity updates  –

URL Filtering
• Multiple language support  –
• Frequent updates (minutes)  –
• Wizard Driven Policy  –

Reputation Filtering
• Provided by top-tier vendor  –
• Mobile/remote user protection  –
• Frequent updates  –

Proxy Filtering
• Real-time proxy detection  –
• Proxy discovery service  –
• Hundreds of new proxies added daily  –

Real-time Malware Scanning

• Real-time  –
• Behavioral  –
• Script emulation  –
• Multi-vector  –
• Bi-directional  –
• Low latency  –
• Frequent updates  –

Call-home detection
• Scan outbound requests  –

HTTPS Scanning
• Proxy encrypted traffic  –
• Financial site exclusions  –
• Certificate validation  –

Content Filtering
• Uses true-file-type identities  –
• Granular policy control  –

Data Loss Prevention

• Works at the desktop  –
• Covers media, devices, web, email  –
• Includes pre-packaged data definitions  –
• Localized across multiple geographies  –
• Easily customized data definitions  –
• Frequent updates  –
• Integrates with encryption  –

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Web security buyers guide

Criteria Sophos Other

Deployment, management and vendor capabilities

Scalable
• Multiple appliance models  –
• Small, affordable branch office appliances  –
• Centralized management/reporting  –

Deployment modes
• Explicit proxy mode  –
• WCCP mode  –
• Transparent mode  –

Directory services integration

• Microsoft ActiveDirectory  –
• Novell eDirectory  –

Management Console
• Up and running in less than 10 minutes  –
• Intuitive user interface  –
• Wizards for common tasks  –
• Online help  –
• Quick easy policy setup  –

Monitoring and Alerting

• Remotely monitored by vendor  –
• Alerting for trouble conditions  –
• Remote remediation  –

Dashboard and Reporting

• Scan outbound requests  –
• Aggregate dashboard  –
• Real-time dashboard  –
• Drill-down dashboard and reporting  –
• Well organized reports by stakeholder  –
• Up to the minute ad-hoc reporting  –
• Automated scheduled reporting  –
• PDF output option  –
• Multi-year data retention  –

Updates and upgrades

• Frequent threat updates 5 minutes –
• Updates and upgrades are automatic  –
• Free upgrades  –

Service and support

• Included 24x7x365 support  –
• Direct access to engineers  –
• Local language support  –
• Replacement warranty on hardware  –

Security labs
• Global labs operation  –
• Hundreds of analysts  –
• Innovative automation  –
• Blended virus, spam, and web threats  –

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