How Routine Pen Testing Can Reveal the Unseen Flaws in Your Cybersecurity Posture

Cybersecurity must evolve beyond reactively handling
breaches and pivoting to protect an organization’s data after the fact. Without
proper precautions, cybercriminals from all over the world can easily take
advantage of vulnerabilities within a company’s Web applications, mobile
applications, APIs, and more. Penetration testing, also known as pen testing,
is a method of cybersecurity in which an expert plays the role of a malicious
actor to expose the holes and flaws within a security infrastructure or
codebase. 

Pen testing is primarily facilitated by dedicated pen testers — some
hired internally and others externally through an agency or freelance service.
My six years at Cobalt have taught me new, unique, and hidden best practices.
It’s my ongoing mission and commitment to spread my knowledge and lessons with other security executives to enhance organizations’ protection efforts.

What Is the Goal of Pen Testing?

Simply put, penetration testing is when
a dedicated group of cybersecurity professionals simulate different
cyberattacks on an application or network to test for potential
vulnerabilities. The goal is to improve the security posture of an organization
and discover easily exploitable vulnerabilities within a security system so the
company can proactively fix them. Bugs are bound to occur, but being aware of
where vulnerabilities lie can polish your product and tighten up your security. 

While many companies invest heavily in building up their infrastructure, the
majority of the steps needed to protect investments happen after deployment. Thus, companies
are left with a reactive response in place, addressing breaches and attacks on
their network once it’s too late. Given the fact that cyberattacks have the
potential to ripple both internally and externally, leaders must take a
proactive approach to cybersecurity, developing at-the-ready responses to
squash incoming threats as they appear.

The merits of pen testing come into the limelight once
organizations recognize the cycle of destruction caused by cyberattacks. This
cycle entails more than the data potentially stolen. It involves the time not
only to address the initial vulnerability but to recover and secure any data
that could have been potentially stolen. Needless time and resources are spent
cleaning up the mess, rather than developing new code. A cycle develops wherein
an organization launches new code into their network, an unforeseen
vulnerability shows up, and the team has to scramble to fix the issue before it
grows even larger. By taking the necessary steps before the new code goes into
production, companies can remove themselves from this vicious circle of
destruction.

According to Cobalt’s “State of Pentesting Report 2021,” pen testing
can be a time-consuming task. In fact, 55% of organizations said it takes weeks
to get a pen test scheduled, with 22% saying it takes months. Modern pen testing
practices use both automated tools and skilled manual testers to ensure maximum
security in an efficient and timely fashion. Staying agile in your
organization’s cybersecurity practices will help cut down on the amount of time
it takes to schedule the proper precautions.

What Are the Outside Benefits?

Pen testing has benefits outside of just vulnerability
identification. Code often is dependent on other code, so frequent pen testing
allows for new code to be tested before it’s deployed into the live build, thus
streamlining the development process and lowering development costs. Frequent
pen testing also provides more timely results, enabling teams to be at the ready
for emerging threats — compared with the standard annual pen test, where
developers won’t be aware of vulnerabilities for months on end. 

In 2021, many
security professionals had to quickly respond to the Log4j threat, but those
who frequently pen tested were prepared to patch the exploitable
vulnerabilities it caused. Due to the insight these developers obtained from
previous pen tests, future code will become more secure, and engineers will
learn from mistakes when developing future versions of their products. The more
often these pen tests happen, the more compliant your products and code will
become.

When to Schedule a Pen Test

The best time to schedule a pen test is — of course —
before an attack occurs. While we cannot predict exactly when a breach will
come, staying proactive and regularly testing and retesting vulnerabilities can
save the company from a vicious cyberattack. Organizations can use pen testing
to prepare new products, updates, and tools for customer or employee use, all
while staying compliant and secure. But for those products to safely go into
the hands of the intended audience, they need to be tested.

Proactivity starts with internally evaluating where
vulnerabilities already exist within a security system. If discovered early,
these vulnerabilities can be dealt with before they take on a life of their own
— ultimately saving the company’s reputation. Take note of all of the assets
your team has (websites, servers, live code, etc.), and set a clear plan for
exposure detection. Once your team is clear on the future strategy and
practices, your pen testers can begin identifying and exposing the
vulnerabilities that may be in your company’s resources. Once the test is
concluded, developers can start remediating any discovered vulnerabilities.

The important takeaway here is, these tests should not be performed
on a one-and-done basis. Pen tests must be executed regularly to ensure
security remains up to date with modern breaching methods. Cybersecurity
changes (and becomes more complex) each day, forcing organizations to be ready
for what’s to come at a moment’s notice.