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pentesting Сентябрь 27, 2021, 4:18
, , , How to do pentesting correctly?

Penetration testing (pentesting) is one of the most effective ways to assess the defenses of a company’s entire digital system or its individual layers. However, this multi-pronged subject raises many questions among customers. Let’s figure out who needs this kind of service, how to choose the right provider, and what results to expect from a simulated cyber incursion.

The need for analyzing the security of enterprise systems co-occurred with the emergence of the “perimeter” concept. A penetration test is one of the fundamental tools in this area. However, the use of this mechanism is often hampered by inconsistencies in the terminology, crude understanding of a pentesting team’s working practices, and skewed expectations of the customers.

What makes a pentest stand out from the crowd?

Those who aren’t very knowledgeable about cybersecurity may find it hard to distinguish a pentest from related terms such as vulnerability testing, red teaming, bug bounty programs, as well as breach and attack simulation (BAS) services and products.

Essentially, a pentest boils down to mimicking an attacker’s actions. Its purpose is to find the shortest and most effective way to reach a target through the perimeter and different tiers of the internal infrastructure. In contrast to this, vulnerability testing is aimed at finding flaws in a system and understanding how to address them. Red teaming is performed covertly, which is exactly how things go during a real-world attack. There is no such restriction during a penetration test.

Bug bounty programs only reflect one facet of pentesting. They are usually limited to the external perimeter, mobile and web applications, and some conditions that may not match a real intruder’s behavior model. In addition, the goal of a bug bounty hunter is to find a vulnerability as quickly as possible and submit a report to get a reward rather than to investigate the problem in depth.

In general, experts highlight two key differences between pentesting and related security activities. Firstly, the testing is done by humans. Secondly, it should include some assessment of the discovered security imperfections, considering how critical the vulnerable infrastructure component is.

At this point, most businesses apply for security experts’ assistance only after receiving respective notices from regulatory bodies. Few organizations purchase pentesting services to probe their perimeter and security facilities as part of proactive defense. This market is very diverse – customers’ requests can range from testing the protection of a fuel sensor to assessing the security of a web application.

How to choose pentesters worth their salt?

Let’s try to figure out what factors to consider when turning to specialized companies, how to find real professionals amid eye-catching marketing claims, and what pitfalls this process may entail. As a rule, the following criteria are the most important in this regard:

  • Team
  • Background and expertise
  • Reputation and established procedures
  • Awards and certifications

However, some of these factors are difficult to formalize, and they do not always give you the big picture. Potential customers should first inquire about the personalities of specific security analysis performers, read their resumes, and draw a conclusion about the qualifications of the contractor based on this information.

Penetration testing: how long does it take and how often to do it?

The duration of a pentest usually ranges from three weeks to a month, depending on the specific task and the size of the target network. Even if the attack surface is relatively small, it may be necessary to spend extra time for in-depth analysis of potential entry points.

In many cases, the process of making a contract between a customer and a security services provider is more time-consuming than the pentest itself. Various approvals can last from two to four months. The larger the client company, the more bureaucratic hurdles need to be addressed. When working with startups, the project approval stage is much shorter.

Ideally, pentests should be conducted whenever the target application undergoes updates. When it comes to a broad assessment of a company’s security posture, continuous pentesting is inefficient – it suffices to perform such analysis two or three times a year.

What details does a pentest report include?

The results of penetration testing should span not only the list of vulnerabilities or misconfigurations found in the customer’s security system but also recommendations on how to fix them. These tend to be general tips since a detailed roadmap for fixing the problems requires a deeper dive into the customer’s business model and internal procedures.

The report mostly includes an executive summary, a list of the discovered vulnerabilities, recommendations, and a comprehensive description of the testing process.

Who should perform a pentest?

Can an organization conduct penetration tests on its own or rely on the services of a specialized organization? Let’s try to dot the i’s and cross the t’s in this regard.

The key problem with pentests performed internally by a company’s security employees is that their view of the supervised infrastructure might be sort of “blurred”. This is a side effect of being engaged in the same routine tasks for a long time. To avoid this issue, it is recommended to involve external pentesters once in a while. In addition to ensuring an unbiased analysis, this will enrich your team’s set of security tools and techniques.

The so-called talent gap is another shortcoming of this approach. Some organizations lack qualified specialists capable of doing penetration tests efficiently. With that said, it could be a good idea to regularly refresh the team of testers working on the same project.


Pentesting is a universal security analysis tool. It can be used to probe the defenses of a company’s entire security infrastructure and search for vulnerabilities in its components or even specific software.

Penetration testing differs from red teaming, vulnerability scanning, and breach and attack simulation in terms of its methods. Not only does it unveil security flaws, but it also shines the light on the ways to address them. Besides trying to spot  security issues, a pentester tries to follow the path of a potential attacker – from the perimeter entry point to a specific area of the target network. 

Even if an organization sticks with in-house pentesting practice, hiring contractors with a decent track record can help it harden its security system. The frequency of the testing usually depends on a specific company’s peculiarities, and the duration of the whole process along with the approval stage can range from one to six months.

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