The Gift of Penetration Testing

Penetration testing is one of the best security investments a business can make. In-house IT or security lacks the objectivity to uncover and thoroughly test for the flaws that expose them to potential data breaches. Having an external ethical hacker can find outstanding and open issues. The benefit of penetration testing is being able to uncover these gaps and weaknesses so they can be quickly addressed. In other words, it gives immediate insight into how to close a hacker’s window of opportunity to compromise your business.

Value Considerations: 
  • Detect hard-to-find security risks, by exploiting layered vulnerabilities, leveraging application scanning and automated network tools from the perspective of a hacker. 
  • Help to prioritize the patching of low-scoring vulnerabilities especially when they can be used to infiltrate with remote code execution or privilege escalation.  
  • Determine the feasibility of the organization’s security to identify and mitigate damage under a variety of cyberattacks. 
  • Help to prevent future attacks by implementing improved security policies and controls resulting from penetration validation. 
  • Help to quantify the need for a bigger investment in personnel and security technology. 
  • Fulfill compliance requirements for security auditing including SOC II, PCI-DSS, CMMC, and best industry practices per NIST. 

Understanding a company’s security defenses used to take a lot of talent and time.  However, technological advances have made it simpler even for IT staff to discover an organization’s vulnerable points. But there is no substitution for a third-party validation by means of a penetration test. 

Penetration testing works by assisting companies and discovering where they are most susceptible and most likely to face an attack. Most importantly is to give guidance on risk prioritization. In addition, how to most effectively resolve weaknesses, this is where good providers excel. Leaving behind an in-depth report without the corresponding details and conversations is not helpful. However, this is the experience that many organizations have. After this many are hesitant to move forward with a pen test as most of the work afterward falls right back on them.  

What are the Basics of Penetration Testing? 

For pen testing, there is a choice between external penetration testers and the use of penetration testing tools. For those with in-house expertise, the benefit of penetration testing tools can help to proactively assess after any significant operational infrastructure or software change. The advancements are continually growing in pen testing and exploit toolsets. However,  they cannot replace the advantage of a third-party penetration tester. While an external pen tester might use similar tools, they have one unique characteristic that your in-house expertise won’t have. They come with a fresh set of eyes and focus based on the scope of the test. Or in other words, an unbiased opinion of the environment, which allows them to objectively think like a hacker. You want this perspective in order to verify the configurations and security controls of your organization.  

A penetration test is an exercise that reviews and attempts to exploit uncovered vulnerabilities and weaknesses and attempts to breach your organization. These testers study and leverage the same tactics as hackers. Their job is to uncover the most likely attack scenarios and execute them in a manner so they do no harm or actually compromise your business data. 

When a penetration tester does penetration correctly, it will create real-life scenarios that inform businesses how well their current defenses would perform in case of a full-scale cyber attack. The feedback from a test can be used to refine security policies, prioritize un-patched vulnerabilities, and identify misconfigurations or gaps in security controls.  

Who is Qualified to Perform a Pen Test? 

The path to becoming an ethical hacker can take many forms. For example, some are experienced developers while others have deep security analyst field experience, and some are self-taught. There are a variety of pen testing certifications for individuals to validate their skills. Verify that your pen tester at least has a few of these certifications. 

Top Penetration Testing Certifications 
  • CEH – Certified Ethical Hacker Certification 
  • GPEN 
  • CPT – Certified Penetration Tester 
  • PenTest+ 
  • ECSA – EC Council Certified Security Analyst 
  • CEPT – Certified Expert Penetration Tester 
  • LPT – Licensed Penetration Tester 
  • OSCP – Offensive Security Certified Professional 

Outside of certification, there are other considerations to evaluate when choosing a penetration tester or organization. The best pen testers have an innate curiosity and are constantly learning and following adversarial tactics as well as having a deep understanding of the capabilities of security technologies. This is something that results in a holistic process and the soft skills that go beyond the knowledge of vulnerabilities and utilization of standard tool suites like Metasploit. Being thorough, having a robust methodology of testing, and the ability to write a clear and actionable findings report are things certifications cannot convey.  

What are the Different Types of Penetration Testing? 

The scope for any penetration test should be identified and agreed upon prior to initiating any activity. Each of these different types of penetration testing has a unique focus and testing methodology taking on the assessment from a hacker’s perspective.  

Network Security Penetration Testing 

Finding vulnerabilities and configuration weaknesses across different networks, systems, printers, hosts, and devices such as switches and routers. It tries to identify the WAN, LAN, and any network segments and uncover the real-life opportunities unauthorized access might be used to access sensitive data. The benefit of this testing helps to find: 

  • Weak or default passwords 
  • Rogue or unmanaged servers on the network 
  • Router-based potential attacks and vulnerabilities  
  • Firewall misconfigurations and firewall bypass IPS or IDS 
  • Unnecessary open ports and services that allow for compromise 
  • DNS configurations and proxy server level weaknesses 
  • Ability to perform a man-in-the-middle attack, FTP, or SMTP attacks 
Web Application Penetration Testing 

Penetration testing investigates how an application handles data if it can be compromised, or susceptible to having service disrupted. It also looks at the applications integrations and the potential a hacker can traverse to other systems or disrupt other services.  Depending on the scope of the engagement various levels of depth can be assessed reviewing the following: 

  • Identify if web-based applications can secure against the various browsers, plugins, and extensions 
  • How the application handles injection and data input flaws 
  • Review components for vulnerabilities and weaknesses like cross-site scripting, and weak session management 
  • API reliability and security 
  • Client-side evaluation for click-jacking, hijacking HTML injection, and potential for redirection 



There are other specialized penetration tests that have their own unique scope and focus that are uniquely designed based on business objectives. 

  • Wireless network penetration testing 
  • Physical and digital penetration testing combined scenarios 
  • Cloud infrastructure specific penetration testing 
  • Operational technology (OT/IoT) penetration testing 
  • Social engineering penetration testing

What are the visibility parameters of a Penetration Test? 

Not only is the scope important in setting the expectations for a penetration test but so are the assumptions on what initial visibility and knowledge the tester has prior to initiating an engagement. Many times, the approach is based on the business objective of the penetration test. 

Black Box Testing (External Penetration Testing) 

In this case, the assessment is carried out with little to no information regarding the IT infrastructure of a business. The main benefit of penetration testing using this approach is to simulate a real-world cyber-attack. Various types of tools leveraging known exploits and human-directed activity are at play to attempt to breach and stress-test the environment as an outsider to the business.    

White Box Testing (Internal or Authorized Penetration Testing) 

Internal penetration testing is when the assessor has partial to full access to the environment or source code. As a result, this knowledge helps them to quickly focus and verify strong systems so they can then utilize more sophisticated layered approaches in their efforts. For instance, this is a great way to test and understand how an attacker can laterally move once they have made their way into your organization delivering insight on internal security policies and procedures.  

Grey Box Testing (Partial Visibility and System Knowledge) 

In this case, the pen tester has partial knowledge of access to an internal network or web application to test. It may begin with user privileges on a host and the objective is to see if they can escalate their privileges to a domain admin or obtain access to other assets or code. This partial view with the system or network diagrams helps them to identify the greatest risk and allows them to review if internal countermeasures and controls are effective.  

What are the differences between Vulnerability Scanning, Pen Testing, and Red-Team Engagements? 

Each of these activities is related but distinct. Most penetration tests use a vulnerability scan to identify and enumerate the associated CVEs or for applications CWEs. However, vulnerability scanning itself is not an assessment. With the growing number of vulnerabilities, no organization can patch 100% of its infrastructure. It is the focus of the pen tester to see if the open vulnerabilities have the capability for privilege escalation (PE) or remote code execution (RCE) or other means that can be leveraged to compromise an organization. The main benefit of penetration testing is, for instance, the ability for an analyst to strategically try multiple vulnerabilities in concert to attempt exploitation.  

Pen testing always has an agreed-upon scope and set expectations in terms of what level of visibility (external/internal) and access a tester will have during their assessment. What is also determined beforehand by both parties is the timeframe that the test will be conducted. Red-team engagements can have similar pen-testing scoping parameters. However, the big difference is that they assess how internal teams react and respond to an active threat. Red-team activities and engagement timing are purposely not shared with the internal security teams (blue teams). In addition to all of the benefits of a penetration test, this type includes the benefit of a simulated test of an attack and a realistic view of how an organization would respond to a real attack. In short, it helps find weaknesses but also tests the incident response and countermeasures in place without causing damage or actual damage to the business. 

How Often Should You Do Penetration Testing? 

Penetration testing should be performed regularly, but at least once a year. There are situations where an external pen testing should be scheduled to validate the security and controls of the business as part of the project: 

  • Large software upgrades or infrastructure changes to your environment 
  • Moving environments (on-premises, data centers, cloud) 
  • Establishment of new office locations or change in VPN services 
  • System and workflow changes related to critical data associated with PCI-DSS, HIPAA, CUI/CMMC, or high-value intellectual property 

Strategic Partners Can Help 

The benefits you get by partnering with a managed security and compliance provider are difficult to ignore. Security-specific focus from professionals with deep IT experience ensures that your findings are actionable. Consequently, reports that give executive summaries, IT specifics, and come with the details so you can reproduce the weaknesses in your environment are invaluable. TECH LOCK delivers end-to-end managed security services and exceptional industry compliance assessments. The benefit of penetration testing with TECH LOCK is that we combine the expertise of human-focused exploit analysis along with the use of an ever-growing set of automated testing tools. With every engagement, we encourage our clients to ask questions, and even challenge our findings. As a result, we are happy to spend a few hours and make sure your team understands the recommendations and priority actions they need to take to protect their business.  

Get in touch if you want assistance in scoping a pen test and focus that is right for your business context or compliance needs.