By Argiro Birba, Senior Manager, Cyber Security Assurance and Angelos David, Assistant Manager, Cyber Security Assurance
Shakespeare never had to scope a security assessment, but Hamlet's dilemma would probably sound familiar to anyone who has.
Penetration testing and red teaming are often mentioned in the same conversation, and sometimes even used interchangeably, when they actually should not be. Both involve offensive security techniques, but they are designed to answer very different questions.
What does a penetration test tell you?
A penetration test is a focused, time-boxed security assessment designed to identify, validate, and demonstrate exploitable weaknesses within a defined scope.
That might mean testing a web application before release, assessing an external or internal network, reviewing cloud infrastructure, or evaluating a mobile application. The scope, objectives, and testing boundaries are agreed in advance so that the assessment can systematically evaluate the areas that matter most.
The goal is not simply to produce a list of vulnerabilities. It is to understand which weaknesses can realistically be exploited, what impact they may have, and what should be fixed.
Penetration testing is particularly useful when validating new applications or infrastructure, assessing significant changes to an environment, meeting compliance requirements, or establishing a security baseline.
Think of it as inspecting a building and checking its locks, windows, alarms, and other possible entry points. You systematically look for weaknesses, test whether they can actually be exploited, and document what needs fixing.
What makes a red team different?
A red team engagement starts with a different question: Could a real attacker achieve a specific objective without being detected or stopped?
The objective might be reaching a sensitive database, accessing customer information, compromising a privileged account, or gaining access to an executive mailbox. How the red team gets there is deliberately less predictable.
Unlike a penetration test, the goal is not to identify every weakness in the environment. The red team only needs to find a path that works.
Depending on the agreed scope, a red team engagement may combine technical exploitation with social engineering, physical access attempts, or other attacker techniques, while placing much greater emphasis on stealth, persistence, and avoiding detection.
The building analogy changes here.
Instead of checking every lock, you hire someone to actually try to get inside without the security team noticing. They probably will not bother with the windows. They will just follow someone through the door while pretending to be on a phone call.
The assessment therefore extends beyond vulnerabilities alone. It tests how people, processes, and technology work together: whether suspicious activity is detected, whether the SOC investigates it effectively, whether escalation procedures work, and whether incident response can contain an attacker who is actively trying to stay hidden.
Which one do you need?
Organizations that are still establishing their security foundations will generally get more value from penetration testing first.
If monitoring capabilities are limited, there is no established security function, or incident response processes are still developing, a red team engagement may simply demonstrate something the organization already suspects: an attacker can get through without being detected.
Running a red team against an organization with no meaningful monitoring is a bit like hiring a burglar to confirm that you do not have an alarm.
A penetration test, in contrast, provides a practical starting point by identifying technical weaknesses, demonstrating their potential impact, and helping teams prioritize remediation.
Organizations that already perform penetration testing regularly and have established monitoring, detection, and incident response capabilities are generally better positioned to get meaningful value from red teaming.
At that stage, the question is no longer just whether vulnerabilities exist. It becomes whether the organization's defensive capabilities can detect and respond to a realistic attacker using multiple techniques and adapting along the way.
Size matters, but maturity matters more.
A smaller organization with strong security capabilities may be ready for red teaming, while a much larger organization may still need to focus on foundational security controls. Larger organizations are simply more likely to have dedicated security teams, a SOC, mature monitoring capabilities, and formal incident response processes, making red teaming a logical next step.
The two approaches are complementary rather than competing.
Penetration testing helps organizations identify and fix weaknesses. Red teaming tests whether an attacker can still find a way through and what happens when they do.
At ADACOM, we have been performing penetration tests for years, and we now offer red team engagements as well.
If you are not sure which one you actually need, ask us. We will tell you, even if the right answer happens to be the cheaper one.