From pentesting to red teaming: what changes in your role and way of working?
Pentesting is about finding vulnerabilities. But a good pentester is not automatically a good red teamer.
Do you work as a pentester and want to transition into red teaming? Or are you looking to establish a red team within your organization? Then it’s essential to understand the difference. In this blog, you’ll learn what sets red teaming apart from pentesting and which skills are required to make that step.
Pentesting VS Red Teaming
As a pentester, you identify vulnerabilities within a defined scope and timeframe. According to NIST SP 800-115, you discover, verify, and report security weaknesses so that an organization can address and improve them.
Red teaming operates within similar boundaries, but the approach is different. As a red teamer, you take on the role of a real attacker and work toward a specific objective, such as gaining access to data or administrator privileges. You don’t just test technology, but also people and processes. Using frameworks like MITRE ATT&CK and TIBER-EU , you choose the path of least resistance and combine techniques such as social engineering, initial access, and lateral movement to turn small vulnerabilities into a successful attack.
From technical execution to operational thinking
Now that you understand the difference, it becomes clear that red teaming requires a different way of thinking. The focus shifts from technical execution to operations. As a red teamer, you follow a realistic attack path and continuously adapt based on the situation. You constantly ask yourself: does this step bring me closer to my objective, what is the likelihood of detection, and is this the right moment to proceed?
Where a pentester often exploits vulnerabilities immediately, a red teamer will sometimes deliberately choose not to act. This may feel counterintuitive at first, but that’s exactly the difference between a technical test and a realistic attack.
Executor & advisor
Red team engagements typically run longer and span multiple layers of an organization. As a result, your role shifts from purely executing to also advising. This requires strong communication skills to manage expectations and interact effectively with various stakeholders, while still being careful not to reveal your full approach.
Working with OPSEC-constraints
In a pentest, you typically rely on well-known tools and methodologies. Red teaming requires a different approach. Everything you do can be monitored, so you must constantly consider how your actions are logged and which detection mechanisms might flag them. This means adapting your tooling and finding alternative ways to stay under the radar. Being adaptable is essential.
Minimum access, maximum creativity
In red teaming, you often start with minimal access to an environment, which requires a different approach. You work in small steps, think logically, and make creative use of what you have. The focus shifts from individual techniques to combining opportunities into a viable attack path. In doing so, you develop essential skills such as creativity, problem-solving, analytical thinking, and perseverance.
How do you transition into red teaming?
If you want to transition from pentester to red teamer, your focus should go beyond learning new techniques and shift toward how you think and operate. Understand why you do something, not just how to do it, develop a deep understanding of your tooling, and continuously keep the bigger picture and your end goal in mind.
During the 3-day training “Red Teaming for Pentesters” at OrangeCon (June 1–3), you will learn how to plan and execute a complete red team operation. Which attack paths do you choose? When do you use specific tools? And how do you establish persistence while staying under the radar? Read more here.
