Is Once-Yearly Pen Testing Enough for Your Organization?

Any organization that handles sensitive data must be diligent in
its security efforts, which include regular pen testing. Even a
small data breach can result in significant damage to an
organization’s reputation and bottom line.

There are two main reasons why regular pen testing is necessary
for secure web application development:

• Security: Web applications are constantly
  evolving, and new vulnerabilities are being discovered all the
  time. Pen testing helps identify vulnerabilities that could be
  exploited by hackers and allows you to fix them before they can do
  any damage.
• Compliance: Depending on your industry and the
  type of data you handle, you may be required to comply with certain
  security standards (e.g., PCI DSS, NIST, HIPAA). Regular pen
  testing can help you verify that your web applications meet these
  standards and avoid penalties for non-compliance.

How Often Should You Pentest?

Many organizations, big and small, have once a year pen testing
cycle^[1]. But what’s the best
frequency for pen testing? Is once a year enough, or do you need to
be more frequent?

The answer depends on several factors, including the type of
development cycle you have, the criticality of your web
applications, and the industry you’re in.

You may need more frequent pen testing if:

You Have an Agile or Continuous Release Cycle

Agile development cycles are characterized by short release
cycles and rapid iterations. This can make it difficult to keep
track of changes made to the codebase and makes it more likely that
security vulnerabilities will be introduced.

If you’re only testing once a year, there’s a good chance that
vulnerabilities will go undetected for long periods of time. This
could leave your organization open to attack.

To mitigate this risk, pen testing cycles should align with the
organization’s development cycle. For static web applications,
testing every 4-6 months should be sufficient. But for web
applications that are updated frequently, you may need to test more
often, such as monthly or even weekly.

Your Web Applications Are Business-Critical

Any system that is essential to your organization’s operations
should be given extra attention when it comes to security. This is
because a breach of these systems could have a devastating impact
on your business. If your organization relies heavily on its web
applications to do business, any downtime could result in
significant financial losses.

For example, imagine that your organization’s e-commerce site
went down for an hour due to a DDoS attack. Not only would you lose
out on potential sales, but you would also have to deal with the
cost of the attack and the negative publicity.

To avoid this scenario, it’s important to ensure that your web
applications are always available and secure.

Non-critical web applications can usually get away with being
tested once a year, but business-critical web applications should
be tested more frequently to ensure they are not at risk of a major
outage or data loss.

Your Web Applications Are Customer-Facing

If all your web applications are internal, you may be able to
get away with pen testing less frequently. However, if your web
applications are accessible to the public, you must be extra
diligent in your security efforts.

Web applications accessible to external traffic are more likely
to be targeted by attackers. This is because there is a greater
pool of attack vectors and more potential entry points for an
attacker to exploit.

Customer-facing web applications also tend to have more users,
which means that any security vulnerabilities will be exploited
more quickly. For example, a cross-site scripting (XSS)
vulnerability in an external web application with millions of users
could be exploited within hours of being discovered.

To protect against these threats, it’s important to pen test
customer-facing web applications more frequently than internal
ones. Depending on the size and complexity of the application, you
may need to pen test every month or even every week.

You Are in a High-Risk Industry

Certain industries are more likely to be
targeted^[2] by hackers due to the
sensitive nature of their data. Healthcare organizations, for
example, are often targeted because of the protected health
information (PHI) they hold.

If your organization is in a high-risk industry, you should
consider conducting pen testing more frequently to ensure that your
systems are secure and meet regulatory compliance. This will help
protect your data and reduce the chances of a costly security
incident.

You Don’t Have Internal Security Operations or a Pen testing
Team

This might sound counterintuitive, but if you don’t have an
internal security team, you may need to conduct pen testing more
frequently.

Organizations that don’t have dedicated security staff are more
likely to be vulnerable to attacks.

Without an internal security team, you will need to rely on
external pen testers to assess your organization’s security
posture.

Depending on the size and complexity of your organization, you
may need to pen test every month or even every week.

You Are Focused on Mergers or Acquisitions

During a merger or acquisition, there is often a lot of
confusion and chaos. This can make it difficult to keep track of
all the systems and data that need to be secured. As a result, it’s
important to conduct pen testing more frequently during these times
to ensure that all systems are secure.

M&A also means that you are adding new web applications to
your organization’s infrastructure. These new applications may have
unknown security vulnerabilities that could put your entire
organization at risk.

In 2016, Marriott acquired Starwood without being aware that
hackers had exploited a flaw in Starwood’s reservation system two
years earlier. Over 500 million customer records were compromised.
This placed Marriott in hot water with the British watchdog ICO^[3], resulting in 18.4
million pounds in fines in the UK. According to Bloomberg, there is
more trouble ahead, as the hotel giant could “face up to $1 billion
in regulatory fines and litigation costs.”

To protect against these threats, it’s important to conduct pen
testing before and after an acquisition. This will help you
identify potential security issues so they can be fixed before the
transition is complete.

The Importance of Continuous Pen Testing

While periodic pen testing is important, it is no longer enough
in today’s world. As businesses rely more on their web
applications, continuous pen testing becomes increasingly
important.

There are two main types of pen testing: time-boxed and
continuous.

Traditional pen testing is done on a set schedule, such as once
a year. This type of pen testing is no longer enough in today’s
world, as businesses rely more on their web applications.

Continuous pen testing is the process of continuously scanning
your systems for vulnerabilities. This allows you to identify and
fix vulnerabilities before they can be exploited by attackers.
Continuous pen testing allows you to find and fix security issues
as they happen instead of waiting for a periodic
assessment.

Continuous pen testing is especially important for organizations
that have an agile development cycle. Since new code is deployed
frequently, there is a greater chance for security vulnerabilities
to be introduced.

Pen testing as a service models is where continuous pen testing
shine. Outpost24’s PTaaS (Penetration-Testing-as-a-Service)
platform^[4] enables businesses to
conduct continuous pen testing with ease. The Outpost24 platform is
always up-to-date with an organization’s latest security threats
and vulnerabilities, so you can be confident that your web
applications are secure.

• Manual and automated pen testing: Outpost24’s
  PTaaS platform combines manual and automated pen testing to give
  you the best of both worlds. This means you can find and fix
  vulnerabilities faster while still getting the benefits of expert
  analysis.
• Provides comprehensive coverage: Outpost24’s
  platform covers all OWASP Top 10 vulnerabilities and more. This
  means that you can be confident that your web applications are
  secure against the latest threats.
• Is cost-effective: With Outpost24, you only
  pay for the services you need. This makes it more affordable to
  conduct continuous pen testing, even for small businesses.

The Bottom Line

Regular pen testing is essential for secure web application
development. Depending on your organization’s size, industry, and
development cycle, you may need to revise your pen testing
schedule.

Once-a-year pen testing cycle may be enough for some
organizations, but for most, it is not. For business-critical,
customer-facing, or high-traffic web applications, you should
consider continuous pen testing.

Outpost24’s PTaaS platform^[5] makes it easy and
cost-effective to conduct continuous pen testing. Contact us today
to learn more about our platform and how we can help you secure
your web applications.