Advanced Pentest: Combined Attacks
- Douglas Leal
- May 13
- 4 min read
When it comes to cybersecurity, it’s essential to adopt an approach that goes beyond basic testing. Advanced pentesting is a specialized technique designed to identify flaws in complex systems and highly protected networks. While standard pentests simulate simpler attacks, advanced pentests focus on sophisticated methods, social engineering techniques, and specialized tools to access and compromise even the most secure systems.
In this post, we’ll explore how advanced pentesting works, why it’s crucial for your cybersecurity strategy, and what you need to know to perform it effectively.
What is Advanced Pentesting?
Advanced pentesting goes far beyond traditional penetration testing, which typically targets vulnerabilities in applications, networks, and servers. It involves a set of advanced techniques aimed at exploiting flaws in more robust security systems and conducting simulated attacks on complex infrastructures, such as private networks, industrial control systems, applications with multiple security layers, and IoT (Internet of Things) devices.
This type of test is designed to simulate sophisticated attacks that could be carried out by highly skilled hackers or cybercriminal groups. The goal is to uncover weaknesses that wouldn’t be easily detected using conventional methods.
Why Perform an Advanced Pentest?
1. Identifying Hidden Vulnerabilities
Complex systems often contain hidden vulnerabilities that cannot be detected through standard penetration tests. Advanced pentesting uses deeper exploitation techniques like reverse engineering, source code analysis, protocol manipulation, and real-time security testing.
🔎 Example: Even in systems with advanced firewalls and strong encryption, vulnerabilities may exist in the source code or communication interfaces that are more difficult to detect.
2. Simulating Real-World Threats
Advanced pentests are the best way to test the resilience of your systems against real-world threats, which are becoming increasingly sophisticated. This includes multi-stage attacks such as spear phishing, zero-day exploitation, and complex exploits that can compromise multiple systems at once.
⚠️ Example: An attacker may use spear phishing to compromise a user and then exploit vulnerabilities in the internal network to expand the attack to other critical systems within the company.
3. Protection Against Insider Threats
Although the focus of advanced pentesting is on external threats, it can also simulate what an internal attacker could do with privileged access to certain systems. This is especially useful for identifying weaknesses in access control and network security.
💼 Example: An internal attacker with administrator permissions might exploit misconfigurations to access sensitive data or alter critical system information.
4. Evaluating Incident Response Capabilities
Another benefit of advanced pentesting is testing an organization’s security team’s ability to respond. With complex and hard-to-detect attacks, both the response and reaction time are assessed. The effectiveness of mitigation procedures and intrusion detection capabilities are tested in a simulated attack environment.
🚨 Example: If, during an advanced pentest, the security team fails to detect or contain the attack in time, this may indicate monitoring gaps or weaknesses in incident response.
How to Perform an Advanced Pentest?
Performing an advanced pentest requires a specialized approach and a series of steps to ensure the right techniques are applied. Here are the main phases of this process:
1. Deep Planning and Reconnaissance
Advanced pentesting begins with detailed planning. This phase aims to understand the system architecture, identify critical points, and map out all potential attack surfaces. Reconnaissance goes beyond simple URL mapping and involves gathering information about internal operations, historical vulnerabilities, and possible structural weaknesses.
🔍 Exemplo: Investigar a infraestrutura de rede e as estruturas de comunicação para identificar possíveis pontos de falha.
2. Exploits de Zero-Day e Técnicas de Engenharia Reversa
Advanced pentesters use zero-day exploits to simulate attacks involving unknown vulnerabilities that can affect systems before a patch is released. Reverse engineering techniques are also applied to software and systems to uncover undocumented flaws.
💡 Example: If a piece of software or device has undocumented vulnerabilities, reverse engineering can be used to identify them.
3. Exploiting Vulnerabilities and Privilege Escalation
The goal during an advanced pentest isn’t just to identify vulnerabilities but to exploit them. Once vulnerabilities are found, the pentester may attempt privilege escalation to gain further control over the system and perform lateral attacks.
🔑 Example: After exploiting a network vulnerability, the pentester might try to access other servers or internal systems within the organization.
4. Combined and Multi-Stage Attacks
Unlike basic pentesting, advanced tests may involve multiple attack stages—such as social engineering, infrastructure vulnerability exploitation, and lateral movement across the organization’s network—testing the resilience of monitoring and mitigation systems.
⚠️ Example: An attack may start with a phishing email and evolve into exploiting network flaws, compromising multiple systems and networks.
5. In-Depth Analysis and Reporting
After conducting the advanced pentest, the final step is analyzing and producing a detailed report outlining the vulnerabilities found, attack methodologies used, and mitigation recommendations.
📝 Example: The report will explain how each exploit was performed, which vulnerabilities were targeted, and what actions should be taken to mitigate the risks.
Conclusion
Advanced pentesting is essential for organizations that want to strengthen their infrastructure security against sophisticated attacks. With cyber threats constantly evolving, implementing this type of penetration test ensures critical systems are thoroughly evaluated and protected.
These tests are especially crucial for companies that handle sensitive data, manage complex infrastructures, and need to be prepared for advanced threats. If you haven’t yet conducted an advanced pentest, now is the time to invest in a deeper security assessment to safeguard your assets and ensure business continuity.
