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Cyber Security Guides

Penetration testing - what, why, and how?

Let’s be honest. No one wants to be hacked or to have compromised data due to an attack such as ransomware. According to data from many sources, however, cyber-attacks are on the rise with 2020 having been a year of heart-wrenching records: more ransomware attacks, more data lost in breaches, and increased sophistication of threats. What is to be done?


One highly recommended way of mitigating cybersecurity risk is to perform in-depth manual penetration testing. Penetration testing is a useful technique to find vulnerabilities in practically any type of software or firmware: web applications, services, operating systems, client-side software and even firmware. The significance of this wide scope cannot be understated – entire organizations have been compromised due hackers attacking small innocuous appearing devices such as smart fish tank gadgets in business offices and then using those to pivot into internal networks. Perhaps even more significant is that security issues are abundant industry-wide. For example, research from Veracode and Enterprise Strategy Group (ESG) found that in 2020, nearly half of organizations regularly and knowingly shipped vulnerable code despite using common security tools and techniques to audit their software. As such penetration testing by third party auditors such as Black Belt Security is at times mandated by customers to vet their vendors in order to secure their supply-chain.

 

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What is a penetration test?

A penetration test, also known as a pen test, simulates the actions of a hacker in a cyber attack against your computer systems in order to find exploitable vulnerabilities (preferably before the bad actors do).  Insights gained from the penetration test can be then used to enhance the computer systems or software in scope. 

How does pen testing differ from a vulnerability assessment?

The goal of a vulnerability assessment is to identify vulnerabilities in a system or network. This technique is used to estimate how susceptible an organization’s networks and applications are to different vulnerabilities.  A vulnerability assessment involves the use of automated network and application security scanning tools to find vulnerabilities. The results of these scans are typically listed in a report. As findings from vulnerability assessments are not backed by an attempt to exploit them, many of them may be false positives. Additionally, due to vulnerability assessments being predominantly automated via tools, they are not suited to detect unique issues such as zero-day vulnerabilities – these often require a trained penetration tester to be found and exploited.


In contrast to a vulnerability assessment, a penetration test involves identifying vulnerabilities in a particular system or network and then also attempting to exploit them. In fact, the purpose of penetration testing includes both to finding vulnerabilities and determining whether a detected vulnerability is genuine. If a pentester manages to exploit a vulnerability, it is reflected in the penetration testing report. The report can also show vulnerabilities there were not found to be exploitable or not attempted to be exploited as theoretical findings. This may be the case where the pentester opts out of exploitation due risk exploitation would pose to the system being tested such as Denial of Service. Don’t confuse these theoretical findings with false-positives – they may be very much 

Why is penetration testing important?

When performed by qualified professionals, pen tests provide detailed information on real-world exploitable security threats. Good quality pen test reports also provide remediation recommendations and a security risk evaluation of the vulnerability found. But why is all this important to an organization? The reasons are many and can include:


  • Identification of security risks and attack vectors proactively to prevent compromise by real-world hackers;
  • Intelligent prioritization of security risks and of remediation tasks;
  • When requiring a third party pentest report from a vendor, an organization can validate that their supply chain is secure or that their vendor is securely handling their data;
  • Verification that existing security programs and processes within the organization are working as intended;
  • Meeting regulatory and/or compliance requirements such as PCI DSS;
  • Discovery of security strengths and validation that the organization’s security strategy is working as intended.

Who performs a penetration test?

In the real world, black hat hackers are often unlimited in time and sometimes even in resources when it comes to attacking a system. An attacker can take years to carefully study a target and its technologies if they so desire. At times, when nation-state threats or corporate espionage is involved, bad actors are comprised of large, well-organized teams determined to get their hands on valuable data. And to win, these attackers need to get it right only once – they need to find one exploitable vulnerability that works for them.  


Penetration testing, on the other hand, is a highly-skilled discipline. After all, a penetration tester must have the prowess to find exploitable vulnerabilities of equal or higher sophistication and complexity than the bad guys – if not, the risk of those vulnerabilities would remain undisclosed to the organization. 


However, with the well-documented cybersecurity skills gap, finding people with the right skills and experience to fulfill such demanding position such as this has become one of the greatest hurdles in the cybersecurity world. Organizations often tackle this challenge and build strong cybersecurity and penetration testing programs by combining resources available intelligently. Manual penetration testing is either conducted by internal teams, comprising of internal employees such as security engineers or external teams, comprising of contractors such as penetration testing firms.


What are the different types of penetration testing?

Penetration testing is typically categorized based on different viewpoints and objectives: Network, web application, engineering, embedded device (IoT), social engineering, mobile, etc. There are many subcategories within each of those categories as well. Network penetration testing, for example, can be divided into internal and external network penetration testing. The former being used to gauge what an attacker with access to internal networks could achieve, and the latter being typically used to test perimeter defenses. Network pentesting can even be as targeted as testing the proper implementation of internal network segmentation or ingress/egress rules for a very targeted scope. Check out Black Belt Security’s guide on different types of pentesting to read more about this subject.

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