Penetration testing is a critical and quite sophisticated component of cybersecurity. Its essence is mostly a simulation of the attacks on different digital assets, such as web or mobile applications, networks, and cloud infrastructures to uncover various vulnerabilities. As with any complex service, penetration testing can present various pitfalls and hidden issues, all of which should be addressed while preparing and executing such projects. Worth mentioning among them:

Uncontrolled Scope Overextension

A quite common and sometimes annoying situation is the expansion of the project’s scope beyond initial agreements. Often it happens because the penetration testing process leads to discoveries that were not part of the original plan, which in turn leads to requests to explore more areas without formalizing scope changes. Such extensions have to be thoroughly discussed and agreed upon because the customer will not want to keep some potentially dangerous areas unattended and the pentesting service provider can’t allow the self-cost to grow beyond agreed limits. 

Business or Technological Process Disruptions

Penetration testing is disruptive by its nature, so no wonder, it can cause unintended disruptions to the services of the customer, especially if pentesting is done in a live production environment. Such downtimes can cost quite a lot. However, with the appropriate approach such dangers can be eliminated or minimized to an acceptable minimum. If there are web or mobile applications to be tested, it could be done in the testing environment; if it goes about other types of assets, all potentially dangerous tests should be coordinated with the customer’s team, and backups of systems and data should be readily available. 

False Positives and Negatives Through Usage of Automated Tools

Some service providers have a certain trend for over-relying on automated pentesting tools, however, they are still far from getting a silver bullet label. Sometimes they can flag valid features as vulnerabilities or miss real vulnerabilities. Of course, automated tools are essential, but relying solely on them can miss nuanced vulnerabilities that require manual inspection. To mitigate these potential project risks, one would still have to use it. The downside of it, however, is that it increases back the complexity of the testing process and takes away the hopes to simplify it through automation.

Data Confidentiality

Never forget that successful penetration testing should lead to accessing confidential data, at least when done on productive systems. To avoid even unintentional breaches of confidentiality, well-defined protocols, and agreements, such as detailed NDA, should be in place between the customer and pentester. 

Cost Overruns

The previous issue carries us gently to the next one, which is the unforeseen escalation of costs due to extended testing times, additional resources needed for a thorough investigation, or unforeseen findings that require more time to investigate and validate. The best mitigation to these risks would be well-considered agreements, settling potential additional efforts, and efficient project management to avoid unnecessary or unforeseen additional expenses.

Reporting Issues 

Reporting is of paramount importance because it will be studied not only by the internal team, but also by the external audit experts, customers, and partners. It must be detailed, actionable, and understandable for both technical and non-technical people from inside and outside. A really good example of the penetration testing report you can get here.

Insufficient Skills

Last, but not least: make sure your pentesting project will be carried out by skilled and experienced professionals. Find out about their certifications, such as OSCE, OSCP, eWPTXv2, and of similar level as well as experience of actual projects. A supplier of quality pentesting services will hold a team of expert ethical hackers knowing their ways of using different tools and finding vulnerabilities others miss.

To summarize, if you are ok with the vendor’s pricing, always look for its references, the certifications, and note the first impression during the intro call. These three elements would be enough to make the right decision.