Practical pentest examples: attack scenarios & best practices

Theory is good, practice is better – the relevance of examples becomes particularly clear in pentesting. In order to make security gaps tangible, CONET relies on practical scenarios in its pentests. So-called kill chains are used: typical attacker routes are simulated step by step to see how a real attack could proceed. In this article, we look at some of these attack scenarios – from the initial reconnaissance to the exploit – and show what lessons can be learned from them for security strategy. Finally, we summarize the most important best practices so that pentests bring the maximum benefit for IT security in the long term.

Table of contents

This post is part of a multi-part blog series. The following articles have already appeared:

Attack chains (kill chains) in the pentest

One Kill Chain describes the phases that attackers go through to penetrate a target system. CONET uses this concept to to design realistic pentest processes. Instead of just carrying out isolated tests, a whole chain of steps is recreated: from reconnaissance to vulnerability scanning and exploitation of found vulnerabilities to propagation in the compromised system. This holistic view not only shows whether a vulnerability exists, but also which path attackers would take to exploit it. In this way, priorities can be set – critical gaps that lead to a complete compromise in a kill chain have the highest priority when it comes to resolving them.

Reconnaissance und Scanning

At the beginning of every attack chain is the reconnaissance phase, i.e. the reconnaissance and information gathering phase. Here a pentester tries Gather as much publicly available information about the target company as possible. These include, for example, IP addresses, domain names, registered subdomains, technical details from public sources or even information from social networks that indicate the technologies used. This information is the raw material from which the attacker plans his next steps.

Scanning follows the reconnaissance. Using tools such as Nmap or OpenVas, the previously identified systems are examined for open ports and services. The goal: Find out what doors might be open. For example, an open port with an outdated or misconfigured service behind it can be a gateway. Systematic scanning produces a map of the attack area – i.e. all points where an attack can possibly be launched.

Exploitation of vulnerabilities in applications

As soon as potential vulnerabilities are identified, the kill chain is about exploiting them in practice. In the area of ​​web applications, for example, this means specifically exploiting vulnerabilities such as SQL injections or insecure authentication. For this purpose, CONET relies, among other things, on exploit frameworks such as Metasploit, which provide a variety of well-known exploits. In this way it can be checked whether a vulnerability found can really be compromised and what consequences this would have.

A practical scenario at this point is a poorly secured SaaS service: Assume that a company uses cloud software whose login system only requires weak passwords. Pentesters could try to gain access using known password lists or exploit known software vulnerabilities. If this succeeds, it is a clear indication that the application urgently needs to be improved. The exploitation of vulnerabilities shows in practice that what consequences failures in application security could have – often a wake-up call for those responsible.

Misconfigurations in the cloud

Modern companies are increasingly relying on cloud services. But it is precisely there that misconfigurations can cause serious security problems. An example that comes up again and again in pentests is a misconfigured one AWS S3-Bucket. Such cloud storage should only make confidential data accessible to authorized people. However, if it is accidentally made publicly readable or – even worse – even writable worldwide, attackers can withdraw or manipulate sensitive company information. Such a case is simulated in the pen test: The testers check whether there are cloud storage or databases that can be accessed without strict access rules.

This scenario illustrates how important correct security policies are in the cloud. A single overlooked check mark in the permissions can open the door to third parties. Through practical tests, CONET uncovers such configuration errors before real attackers find them. The results are then incorporated into concrete recommendations – such as making access rights more restrictive or setting up monitoring mechanisms that report unusual access.

Best Practices im Pentest

Some best practices for conducting and following up on pentests can be derived from the practical examples:

• Regular security checks: Pentests should be repeated at appropriate intervals in order to discover and close new vulnerabilities in a timely manner.
• Continuous adjustment of the strategy: A company's security strategy must be continually developed and adapted to current threats. Ideally, findings from each pen test flow directly into improvement measures.
• Collaboration between internal and external: A pen test is most beneficial when internal IT departments cooperate closely with external testers. Open communication and knowledge transfer ensure that no knowledge is lost and the measures can be implemented in a targeted manner.
• Training and awareness: Technology alone is not enough. Regular training helps employees to act in a security-conscious manner – be it in recognizing phishing emails, carefully handling access authorizations, and establishing clear responsibilities.

These best practices ensure that pentests are not viewed as isolated events, but as part of a long-term security approach.

Conclusion

Practical pentest examples impressively demonstrate where the critical weak points lie in a company – in all areas from technology to people. The use of kill chains and realistic attack scenarios makes the results tangible and convincing. It is important to consistently implement the lessons learned from each test. A pentest is most effective when it is understood as part of a holistic security strategy that includes both technical and organizational measures. Only with this comprehensive approach can companies be effectively protected in the long term and the findings from pen testing practice converted into sustainable security gains.

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Sebastian Kokott is a senior consultant at CONET. As an IT security expert, he understands the importance of a robust security concept to protect company data and systems from threats.