As you might have already discovered, an exceptional tool in the fight to ward off cyberattacks, hacks and other virtual threats for businesses working with payment cards and consumer information is the penetration test.

Sometimes referred to as a pen test—and it is commonly called ethical hacking—this controlled and simulated cyber attack against your business’s system checks for any exploitable vulnerabilities. A pen test may involve attempting to infiltrate a number of application systems like application protocol interfaces (APIs) or frontend and backend servers to reveal vulnerabilities. Put simply, a penetration test gives you that golden opportunity to beat hackers to the cyberpunch in a safe environment while gathering key information to thwart any upcoming cyber attacks.

Perhaps you have had lackluster results from previous pen tests, or you simply want to fine-tune your approach. Either way, sitting down with your team to answer some key questions may help you get the results you want in order to better protect consumer data entrusted to your organization.

Our team sat down together and came up with six key questions for you to consider before launching your next pen test to achieve the best possible results. Take a look to see which ones you believe might help you.

1. Why Perform a Penetration Test?

There are a number of reasons why it is a good idea to perform a penetration test, like the following:

  • A customer request
  • Executive management is planning a company change that requires proof that your system is healthy
  • A good and regular practice of promoting cybersecurity health within your organization, as a standard rule

2. Is Penetration Testing More Effective Than a Vulnerability Assessment and Other Security Testing?

This question is really common, but it is essential to determine whether a penetration test or vulnerability assessment is the best way to evaluate your system. A penetration test is a realistic simulation of an actual hacking attack, targeting vulnerabilities that may be present in your computing infrastructure and line servers. An ethical hacking event helps you to detect and analyze any points of weakness or failure so you can make specific corrections and improvements.

A vulnerability assessment is not as intrusive since it does not require an active infiltration of your computing environment. This test gives you a solid overview of the general health of your computing system and its vulnerabilities, but it does not provide the deeper insights of a real hacking event that a pen test offers.

Frankly, no other type of security testing currently exists that returns the type of in-depth and real-time information of a pen test for IT teams trying to understand where your vulnerabilities lie and how hackers may try to compromise them.

3. Which Method or Process Is Best for Performing a Penetration Test?

Each organization may develop its own process, technique or method for approaching a penetration test, but there are some core principles and activities in common among all penetration tests.

Following are a few methods from which you can choose to perform a pen test for your organization:

Internal Testing.

An internal test focuses on your business’s local area network (LAN), as well as your laptops, computers, switches, printers and other devices located within your office. When performing an internal test, a tester who has access to an application protected by the firewall pretends to make an attack as if by a “malicious insider.” The test does not assume that the employee necessarily had bad intentions. Testers usually approach this type of a test without assuming malicious intentions since it is just as common for such attacks to happen due to an employee’s credentials having been stolen via a phishing attack.

External Testing.

In external penetration testing, the tester targets the visible assets of an organization on the internet, such as on the company website or on email and domain name services (DNS).

Blind Testing.

With blind testing, the testing person only receives the name of the organization under testing attack, which gives security personnel a real-time glimpse into the way that an actual application assault might happen.

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Double Blind Testing.

Basically, a double blind test is a surprise attack. Security personnel receive no advanced warning that a simulation attack is on the horizon. This test is a good opportunity to see a boots-on-the-ground approach to defense against an attempted breach.

Targeted Testing.

This type of testing method features the tester and security personnel work as a team and keep each other updated regarding their respective movements. More of an instructive exercise, targeted testing is a valuable training tool that also offers real-time feedback.

Read more about the different types of penetration testing here.

4. Is It Better to Do a Pen Test in a Production or Pre-Production Environment?

A major advantage to performing a pen test in your production environment is that you are seeing what happens under actual conditions while using your website, website application or API, using the latest developments that your team has updated. The only small possible downside to live pen testing during production is that it may interfere with normal operations. The solution to this potential problem is running your test in an ISO-production environment that is identical to your production environment. With this approach, you still get the value of a true simulation without the risk to your live environment.

Performing a penetration test in a pre-production environment is not all that different from performing it in the production environment. One key variation is that this test has no chance of touching services accessed by your users or customers. A pre-production penetration test is ideal for reviewing critical infrastructure integrity.

5. What Is the General Flow or Life Cycle of a Penetration Test?

Developing an overall flow or life cycle for your ethical hacking event arms you with a solid and meaningful plan of attack. Without a solid and meaningful plan of attack, your pen test may return results that look like some sort of random scan. And you probably don’t want to perform a simulation of an attack with no meaningful data to show for it.

Here is just one lifecycle example that may work for your penetration test:

Discovery and Reconnaissance.

During this recon phase, you get the chance learn everything possible about your organization, within the defined scope of the specific pen test. Learn more about personnel, online services, systems and more. Here, you might discover and neutralize a vulnerability that could provide important information via the public domain that can boost an attacker’s efforts.

Scanning and Probing.

Here, your tester will simultaneously run both a manual and automated process to identify vulnerabilities. The automated and manual testing should run parallel, yielding the same results in real-time.


Once the tester has identified an issue, he or she will try to exploit it. The most experienced testers will eschew tools to get around obstacles like antivirus software. The process in this scenario requires testers to creatively and earnestly compromise confidentiality, integrity and, at times, availability of a system.


When your tester has exploited a vulnerability, he or she will use that access or information to gain additional access to the resource or system. At that point, the cycle repeats.

6. What Is the Best Preparation for a Pen Test?

One of the best strategies to prepare for a pen test is to identify a list of assets you want to test then setting up a meeting or scoping call with your auditing team that specializes in pen testing.

Are You Ready for Your Upcoming Penetration Test?

Have these questions and answers helped steer you in the right direction for your own upcoming penetration test? If you can use more help, our I.S. Partners penetration testing team is here for you.

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