What Is Penetration Testing?

If you want to know whether your cybersecurity strategies are working as intended, you’re faced with one of two realities. You can wait for a bad actor to breach your network and then deal with the fallout, or you could regularly conduct penetration testing. But what is a penetration test?  

In this guide, we’ll break down:

  • What is penetration testing?
  • Why is pen testing important?  
  • Pen testing tools
  • The five penetration testing stages
  • Pen testing methods

What Is Penetration Testing?

Penetration testing—or pen testing—is a test methodology in which security teams mimic real-world cyberattacks to identify and exploit weaknesses in an application, computer system or network. 

Like how the military conducts war games to judge the preparation of troops in an actual combat situation, a penetration test appraises the capabilities of your cyber defenses. If successful, it will identify potential avenues by which a malicious actor could bypass security features to probe your system further. 

Because it’s just a test, the “hack” will not negatively impact your organization. 

Why Is Pen Testing Important? 

To properly gauge the efficacy of your virtual defenses, a penetration tester can’t take half-measures. They’ll engage in actual attacks, leveraging the same tools and techniques a real hacker would use to gain access to your system. 

Doing so allows them to replicate the most realistic scenario possible.  

Therefore, a thorough pen test won’t stop after successfully identifying potential gaps in your perimeter. Instead, once a vulnerability is discovered, the ethical hacker will probe and prod it, seeing just how deeply they can sink their claws into your system. 

By pushing your cyber defenses to their utmost limits, you empower your organization to: 

  • Evaluate the capability of your security measures and determine their responsiveness to real-world attacks 
  • Identify exploitable or circumventable gaps within your computer systems, networks, websites or applications
  • Determine how much damage a motivated hacker could cause if they successfully gained access
  • Verify the extent to which a system device or process is protected  
  • Establish controls you could implement to address security vulnerabilities
  • Assess your organization’s regulatory IT compliance according to frameworks like NIST (National Institute of Standards and Technology) 
  • Test employees’ security issues awareness, practices and capabilities, particularly in response to social engineering efforts  

What’s the Difference Between Pen Tests and Vulnerability Scans?

Some mistakenly treat pen tests and vulnerability scans as one and the same.

While pen tests and vulnerability assessments share similarities because they both search for vulnerabilities within your system, pen tests go a step further.

Imagine your security system as a castle. A vulnerability scan would be like circling the entire perimeter wall to see if there were any open gates or ones that could be opened. Once the scouting was complete, the scanner would return to relay its findings. 

On the other hand, a pen tester would not immediately return after a gap in the defenses was discovered. Instead, they’d enter through openings to see if they could bypass the additional layers of the castle’s defenses to reach their goal: your data.    

Both methodologies serve a valuable purpose, but penetration testing ultimately provides more comprehensive and actionable information. 

Pen Testing Tools 

During the various phases of a simulated attack, a pen tester will utilize several different tools, techniques and methodologies. Although it may depend on the professionals conducting the assessment, common pen testing tools include: 

  • Port scanners – These programs diagnose network and connectivity issues, gathering data on the test target from a remote network location. They probe network ports or services to determine which services are available for connection within the target system. 
  • Vulnerability scanners – These operate similarly to port scanners, except they go a step further by attempting to exploit known vulnerabilities within the targeted system. This enables a tester to quickly and comprehensively identify:
    • Security defects
    • Configuration weaknesses
    • Unpatched software 
  • Application scanners – These programs will assess the baseline functional behavior of an application, then perform systematic attacks against it, such as: 
    • Cookie manipulation 
    • SQL injections
    • Buffer overruns
    • Cross-site scripting (XSS)
  • Web application assessment proxies – These insert themselves between the tester’s web browser and the target’s web server, enabling a tester to view and manipulate data moving between the two endpoints. 

The Five Penetration Testing Stages 

A penetration test isn’t a singular process. To derive the most value from the exercise, there are five stages set before, during and after the test occurs.  

Step 1: Planning

This is known as the pre-phase portion of penetration testing. During these initial preparations, your first task is to outline the scope of the test by setting: 

  • Expectations
  • Goals
  • Objectives
  • Legal implications

Carefully mapping out the test allows the assessor to understand your organizational culture and risk profile better. Equipped with this knowledge, they can determine the necessary test type and set contingency plans to minimize potential service disruptions.    

Step 2: Scanning

Once all the relevant data has been gathered, pen testing can begin. First, the tester will deploy various automated scanning tools to identify exploitable vulnerabilities. Their goal is simple: find as many potential entry points as possible.  

Step 3: Gaining Access

After a high-risk vulnerability has been identified, the pen tester will attempt to gain further access to the system by simulating real-world attacks via safe exploitation techniques like:

  • Manual processes
  • SQL code Injection
  • Pen testing tools  

Having gained initial access, they’ll attempt to pivot to other systems or networks, documenting their actions and findings as they go. 

Step 4: Analysis & Review 

Upon completion of the test, the assessors will compile a comprehensive report detailing their processes, results and conclusions. This will often include: 

  • Scope of the test
  • Testing methodologies 
  • Findings (known vulnerabilities and present risk ratings) 
  • Remediation guidance  
  • Assessment of overall regulatory IT compliance  

Moving forward, your organization can take the proper security measures to correct pressing issues and install cybersecurity best practices that prevent vulnerabilities from being exploited.     

Step 5: Retesting

After the recommended corrective measures have been implemented, it’s vital that you perform retests. Doing so allows you to identify whether the prescriptive actions were successful or if further steps need to be taken to bolster your defenses. 

Pen Testing Methods 

Before you prepare to conduct a pen test, it’s paramount that you’re familiar with the different types of pen tests available. Each serves a different purpose, and certain variations may better suit your organizational needs. Ethical hacking methods include the following. 

External Testing

This type of pen test focuses on the company’s IT infrastructure—web servers, website hosting and devices—accessible via the internet. The hacker’s goal is to gain unauthorized access to:

  • Applications
  • API endpoints
  • Emails
  • Domain servers 

Once access is gained, they’ll attempt to extract valuable information that they could use to probe the system further.  

Internal Testing 

Also known as white-box testing, this type of pen test grants the assessor a head start by providing them with access to the open source code and software architecture. It simulates an attack from a rogue employee who already had some measure of system access and privileges.  

Blind Testing 

Also known as black-box testing, this methodology simulates an attack from outside your organization, often via a brute force attack. 

The test requires that the assessor start with little to no information about your organization’s IT infrastructure, including the applications, source code or architecture. Mimicking a real-life hack allows you to identify: 

  • How an outsider would breach your defenses
  • How they would move through your system once they had gained access  
  • How much damage they could cause

Double-Blind Testing

With a double-blind test, the IT team is unaware of the impending trial. 

This allows the organization to evaluate how they respond to what they believe to be an actual attack. In addition, it measures the efficacy of an organization’s IT response, particularly regarding monitoring, incident identification and response procedures. 

Targeted Testing

Sometimes referred to as a “lights-on test,” a targeted test involves the internal IT team and external pen test specialists working in tandem throughout the process. Both parties are fully informed of when the test will begin and end. 

Trust Helixstorm with Your Penetration Tests 

Pen tests are vital techniques organizations can leverage to assess their cybersecurity defenses. And with the evolving nature of cybercrime, they must be conducted frequently to defend your organization’s mission-critical systems and data from newly emerging threats.

But who can you trust to execute a pen test properly? That’s where the experts at Helixstorm come in. At Helixstorm, penetration testing is just one of the many ways our Managed Security Services detect and defend against cyberthreats.

If you want to keep your business safe, contact us today.