Cybersecurity is no longer an option—it’s a necessity. Whether you’re preparing for certification, launching a new product, or simply want to assess your company’s current security status.
A penetration test (pentest) helps identify real vulnerabilities before attackers can exploit them.
However, many companies are faced with the same question:
Which penetration test is actually the right one for us?
This article will guide you through the process of finding the right penetration test in 4 steps:
Step 1: Identify the reason for a penetration test
On your own initiative? At the customer’s request? A requirement for an upcoming certification?
Why do you need a penetration test in the first place?
This has a significant impact on what kind of test makes sense.
Here are a few common reasons and the recommended penetration tests derived from them:
Many companies need a penetration test due to regulatory requirements or certifications such as:
- ISO 27001
- TISAX
- Customer Requirements
- Supplier Evaluations
The main focus here is on:
- Documented Procedure
- Professional Reports for Auditors
- Evidence of a structured security process
Recommended Penetration Tests:
- Penetration test of the external IT infrastructure (black-box)
- Penetration Testing of a Web Application (Black-Box and Gray-Box)
- Penetration tests on the internal IT infrastructure and Active Directory (black-box and gray-box)
These tests help ensure that compliance requirements are fully met and that audit requirements are satisfied.
If you want to release a new product, it is essential that you test it before the release.
It is important that the product be evaluated from the perspective of a real end user.
So the focus is on:
- How people use the application or IT component
- Which features and data are available
- What risks may arise for real users and data
Recommended Penetration Tests:
Depending on the product you want to have penetration tested before its release. For example:
- Penetration Testing of a Web Application (Black-Box and Gray-Box)
- Penetration Testing of a Mobile Application (Black-Box and Gray-Box)
- Penetration Testing of an API Interface (Black-Box and Gray-Box)
- Penetration test of the external IT infrastructure (black-box)
- VPN servers, Citrix, RDP gateways, FTP/SFTP servers, and much more.
Many companies want to know:
What could a real attacker actually compromise today?
This isn’t just about individual applications, but about the overall security situation.
Recommended Penetration Tests:
- Penetration test of the external IT infrastructure (black-box)
- Penetration tests on the internal IT infrastructure (black-box)
- Security Analysis of the Active Directory Directory Service (Black- and Gray-Box)
- An important extension of the penetration test would be an additional analysis of a typical employee workstation (e.g., a Windows 11 laptop). It is precisely these client devices that attackers target first to gain “initial access” to your internal corporate network.
- Phishing and Social Engineering Campaigns
- Fake emails, manipulated phone calls, tailgating, or tampered USB drives. How do your employees respond to real-life attack attempts? Tests like these reveal how employees act in critical situations and where targeted awareness training is needed.
This combination provides the most realistic overall picture and allows for a high degree of customization to fit your company’s structure.
When regular penetration tests are no longer enough.
Do you already conduct penetration tests on a regular basis? Is your IT infrastructure continuously monitored by IDS/IPS/EDR/XDR/MDR/NDR, as well as SIEM and SOC teams? Are employees regularly trained and made aware of the risks through phishing awareness campaigns? Is Network Access Control (NAC) implemented and hardened? Are access controls such as RFID/NFC locking systems, trained reception staff, night watch, and two-zone security gates in place?
Then it’s time for the next step:
- Covert penetration tests conducted under real-world conditions without prior notification.
- Realistic phishing campaigns designed to steal genuine login credentials or execute malicious code.
- Red Teaming and Purple Teaming assessments based on MITRE ATT&CK.
Together, we’ll identify the remaining vulnerabilities in your security architecture before real attackers exploit them.
Step 2: Take the attacker’s perspective
Not every attacker starts with the same conditions.
Therefore, before each penetration test, it is important to define the perspective from which the test will be conducted and what prior knowledge will be used.
External attacker
An external attacker initially has no access to internal systems and gathers information from sources that are publicly available (OSINT).
Internal Attacker
This scenario assumes that the attacker already has access to internal resources, for example through:
- a compromised employee computer
- VPN access
- an insider or a bribed, malicious employee
- a device that has been infiltrated into the network
An attacker’s prior knowledge
Regardless of whether the attacker is external or internal, prior knowledge also plays a significant role.
There are three categories of penetration tests:
- Black-Box
- No information, or only minimal information, about the target environment. Simulates a realistic external attack. The attacker must gather information independently.
- Grey-Box
- Limited information or user accounts are available or provided. This often simulates a compromised employee or customer account and reduces the initial effort required by the penetration tester to gather information passively. The time saved can be better utilized for in-depth analysis.
- White-Box
- Comprehensive information, such as source code, architecture, and admin credentials, is known or provided. Focus on maximum technical testing depth. Simulation of an employee with full knowledge.
Step 3: Find a high-quality Pentest provider
Not every provider and penetration test offers the same value.
Likewise, the cheapest provider isn’t always the best choice—especially when quality, experience, and realistic attack simulations are what determine your company’s actual security.
A common mistake is choosing a provider that primarily performs automated scans. The same applies to purely AI/KI/LLM-based penetration tests (AI penetration test agents). Such fully automated vulnerability scans are not sufficient on their own, even if these providers and the current AI/KI boom may promise otherwise.
Automated tools or AI/KI/LLM often only find:
- Known Vulnerabilities
- Known Standard Issues
- Known Configuration Issues
However, they often fail to realize:
- Complex attack chains
- Business Logic Errors
- Individual Security Issues
- Real-world attack scenarios
- Ways to bypass security tools such as a WAF, IDS/IPS, and next-generation firewalls
- That the identified vulnerabilities were a false positive or a hallucination.
That is why a high-quality penetration test should always include manual testing methods and a human expert.
What to Look for in a Provider
In another post (Click here), we explain in detail the most important quality criteria to consider when choosing a provider.
In summary, we recommend that you pay attention to the following:
- The penetration test is conducted primarily manually.
- The penetration testers hold industry-recognized certifications (e.g., OSCP, OSEP, OSWE, BSCP, CRTP) and are named by the provider for each penetration test. We do not use interns, working students, or subcontractors (e.g., from abroad) to conduct your important penetration test!
- We provide clear and actionable reports, including corrective measures.
- The provider itself is ISO 27001 certified.
Especially when it comes to sensitive company data, it is important that the service provider also adheres to professional security standards.
Step 4: Get a Transparent Quote
Many companies waste time unnecessarily even before the actual penetration test begins due to:
- Sales and Marketing Meetings
- Initial appointments, including an introduction and orientation
- Lengthy bidding processes
Often, a lot of time passes before there is even a realistic initial price estimate or a clearly defined scope of work.
Since our company was founded, we have been committed to creating greater transparency in the field of offensive security and penetration testing. In our view, this includes transparent pricing, a quick way to obtain comparable quotes, and professional consultation both before and after the test.
With our penetration test configurator (Click here), you can:
- Easily select the right penetration tests yourself.
- Define and customize the scope of the test.
- Get a transparent quote by email right away.
- Available in both German and English.
- View all costs and procedures transparently at any time.
- Discuss your options with an OSCP-certified penetration testing expert within 24 hours.
Conclusion
A penetration test should never be viewed merely as a mandatory task or a compliance checkbox. The true value is realized only when the test is tailored to your goals, your infrastructure, and your specific risk profile.
Whether it’s external infrastructure, internal systems, applications, or complex product landscapes, choosing the right penetration test, the appropriate attacker perspective, and an experienced provider is crucial to the quality of the results. A professional penetration test not only helps identify vulnerabilities but also improves security processes in the long term and mitigates real risks early on.
That is precisely why we focus on transparency and practical advice rather than unnecessarily complicated sales processes.
With our penetration test configurator (Click here), you can customize the scope of the test to your needs, select the appropriate test types, and immediately receive a transparent price estimate. This allows you to quickly determine—faster than with other providers—which penetration test best suits your needs and which services or test types fit within your budget. Our OSCP-certified penetration testers will then review your configuration and get back to you as soon as possible.