Cybercrime is constantly evolving – in terms of tactics, technology, and speed. Companies can no longer rely on sporadic security checks, but must continuously review their IT landscape from various angles – both technically and organizationally. If you want to understand your own line of defense, you need to know the methods of potential attackers – and test them specifically.
Two of the most effective methods for doing this are penetration testing (pentesting for short) and red teaming operations. Although both approaches are often mentioned in the same breath, they pursue different goals and have different focuses.
In this article, we explain the difference between the two methods and provide you with practical decision-making guidance for your company.
Pentesting: Systematic testing for vulnerabilities
A penetration test is a controlled attack on IT systems. The aim is to identify, exploit, and document as many security vulnerabilities as possible within a given period of time – but under clearly defined conditions.
The responsible personnel are informed about the test and are in contact with the testers.
In practice, different variants are often carried out – including tests of the external and internal environment as well as application-specific tests such as web application, mobile app, or cloud pentests.
Typical pentest process
- Planning – Defining the scope, contact persons, communication channels, and time frame
- Reconnaissance – Gathering information about the target systems
- Vulnerability Assessment – Identifying potential vulnerabilities
- Exploitation – Attempting to exploit vulnerabilities
- Post-Exploitation – Evaluating which data or systems are affected by a successful compromise
- Lateral Movement – Possible spread to other systems using vulnerabilities found
- Reporting – Documenting the results with specific recommendations for action
Red Teaming: Realistic simulation of an attack
A red team assessment is a scenario-based emulation of a targeted attack on the company. In particular, it tests the interaction between technology, people, and processes.
Before the assessment begins, a time frame is defined and a specific goal is set – such as obtaining confidential personnel files, accessing certain systems, or secretly installing malware. Unlike a penetration test, no exact time is agreed upon, only a variable time frame during which actions can take place. Furthermore, no information about existing systems or protective measures on the customer's side is passed on to the testers. To ensure that the objective is achieved, great importance is paid to ensuring that the measures carried out are discreet.
Only a few people within the company being tested are informed about the nature and duration of the engagement. The tools, techniques, and procedures used are not restricted and often also include social engineering or physical intrusion into buildings.
Typical red team assessment process
- Planning – Defining the goal to be achieved, contact persons, communication channels, and the time frame
- Reconnaissance – Extensive collection of all available information about the company, including darknet research, social engineering if necessary to obtain further information about internal security measures and possible target systems, as well as reconnaissance of suppliers and partners (supply chain evaluation)
- Target Identification – Identifying a possible attack path to achieve the defined goal, possibly recreating the customer environment, developing possible exploits and strategies
- Gaining Access – Accessing the company through vulnerabilities identified in the previous phases, possibly gaining access to buildings and bringing in hardware
- Establishing Foothold and Maintaining Presence – Maintaining the access achieved and spreading and expanding rights in the company's infrastructure
- Completing Objectives – Possible exfiltration of data, provision of evidence of target achievement, and documentation
Pentest vs. Red Teaming – A head-to-head comparison
Criterion
Penetration test
Red Teaming
OBJECTIVE
Identification and exploitation of technical vulnerabilities
Simulation of realistic, targeted attacks on processes, technology, and people
TIME FRAME
Defined start and end times
Definition of a time frame in which activities can take place
ATTACK SURFACE
Predefined systems or applications
Entire organization with a focus on a specific attack target
TEST SCOPE
Scope, methods, and systems are defined in advance, broad investigation
Focus on achieving the specific goal, red team acts autonomously and creatively
APPROACH
Structured, methodical, technology-oriented
Dynamic, realistic, scenario-based
TYPICAL METHODS
Vulnerability scans, exploits, configuration checks
All tactics, techniques, and procedures from an attacker's repertoire
MATURITY REQUIREMENT
Entry-level test for IT security analysis
Advanced test – builds on existing security measures
TARGET GROUP BENEFITS
Ideal for securing individual applications, networks, or after system updates
Tests the resilience, detection, and response capabilities of the company as a whole
TYPICAL USE CASES
Regular testing, before go-live, after migrations, to meet NIS2/CRA requirements, during ISO/IEC 27001 audits
After regular pentests, for blue team validation, for TIBER-EU/DE/DORA requirements
RESULTS
Technical report with specific vulnerabilities and proposed measures
Attack report including success path and strategic recommendations
Pentest or Red Teaming – which is appropriate in which situation?
Our recommendation:
Start with a pentest if you:
- Have never performed a comprehensive security audit before
- Want to identify technical vulnerabilities in web portals, interfaces, or networks
- Want to test a clearly defined system area
- Need to meet requirements based on NIS2, CRA, or in the course of ISO/IEC 2700 certification
Use Red Teaming if:
- The organization's security level is already high, both technically and organizationally
- You want to test your organization's resilience to realistic attacks
- You want to know how effectively your Blue Team detects and defends against attacks
- You need to meet regulatory requirements such as DORA, TIBER-DE, or TIBER-EU in the financial sector
In short: Red Teaming is not an entry-level test, but a stress test that shows what a real attack could look like.
Conclusion: Security is not a product – it is a process
A one-time security check is not enough to protect your company from today's cyber threats. A professional pentest provides you with the technical foundation you need: you identify specific vulnerabilities, prioritize risks, and initiate targeted countermeasures – for example, through rule-based vulnerability management, hardening of system configurations, firewall optimization, or access rights checks.
With a red teaming operation, you go one step further: you gain insight into the actual attack dynamics – including the human factor. Based on the findings, security awareness training, incident response playbooks, SIEM fine-tuning, or technical detection mechanisms can then be further developed in a targeted manner. You can also systematically increase the effectiveness of your Blue Team – for example, by introducing Purple Teaming or regular detection and response exercises (tabletop tests).
In short, pentesting and red teaming not only deliver results – they provide a concrete basis for action to expand your IT security strategy, tailored to the maturity level of your organization.
Would you like to know what a targeted test of your IT security might look like?
Our offensive security team at Possehl Secure will be happy to advise you.
Get in touch with us – and put your company to the test before real attackers do.