How do you prepare for a successful penetration test?

Preparing for a successful penetration test involves a meticulous blend of strategic planning, thorough reconnaissance, and robust technical expertise. Firstly, it's imperative to define clear objectives and scope, outlining specific targets and potential vulnerabilities. Conducting a comprehensive assessment of the target environment, including network architecture, applications, and system configurations, is crucial. This involves gathering as much information as possible through both passive and active reconnaissance techniques. Finally, thorough documentation and reporting of findings, along with actionable recommendations, are essential to conclude the penetration test successfully.

Clearly articulate the objectives and goals of the penetration test. Understand the specific reasons for conducting the test and what the organization aims to achieve through the assessment. Identify and list the assets, systems, and networks that are within the scope of the Pentest. Common methodologies include OWASP for web applications, OSSTMM for infrastructure, and PTES (Penetration Testing Execution Standard). Ensure that the penetration test complies with legal and regulatory requirements

To prepare for a penetration test successfully, you should follow these steps: 1. Define the Scope. 2. Obtain Permission. 3. Gather Information. 4. Identify variability. 5. Exploit Vulnerabilities. 6. Document Findings. 7. Report and Discuss Findings. 8. Remediation and Retest. 9. Continuous Improvement. Penetration testing should be performed by experienced professionals who have the necessary skills and knowledge to conduct the tests safely and effectively. And important to follow ethical guidelines and respect the privacy and confidentiality of the systems or networks being tested.

Penetration testing are great way to test with low signal ratio and more precise finding. Pentest can also help in identifying fault in business logic - identify the elements that need to be tested - define a scope that is in line with a full application testing and will allow the - start with a black box (no info) testing and gradually provide information working towards a white box texting Obejctive of a pentest should not identify vulnerabilities that could be detected by a vulnerability scan and pentest should be used in conjunction with a vulnerability scan

As the pentester, work with the customer to help them identify what their ultimate goal is. Is there a particular system they are concerned about? Are they looking to meet regulatory compliance? Is the engagement purely a formality for some other deciding body? They may not fully known what they want/need. Guiding them and providing your expertise can expedite and ensure a thorough scope is decided upon. As the recipient, be honest, upfront, and humble. The folks performing the pentest are not your enemy, and your not "tipping your hand" by disclosing sensitive systems prior to the start of the engagement. Trust in your pentester; they only want what is best for you and your company.

While it does have a place in the toolkit, black box penetration testing is overall not to be trusted for a reliable assessment of your risk. A fully credentialed white box test, conducted in the same time, will find far more issues, and they will be far less superficial.

Beyond the black, white, or gray box approaches, the method should reflect the most realistic threat scenarios for the organization. While a black box might simulate an external attacker, does it account for threats like insider attacks or social engineering that your organization might be particularly susceptible to? The method should mirror real-world threat vectors.

Inform relevant internal teams about the test and its scope to ensure normal operation is minimally impacted and false positives (like misinterpreting the test as a real attack) are avoided. Ensure your systems have appropriate backups and recovery processes in place in case of any unintended disruptions.

When considering different pentest methods, it's also worth looking at the objectives and drivers behind the pentest itself to make the right choice for what the company is trying to accomplish. Whether it is a regulatory requirement, external attack surface assessment or part of the internal application security programme, it might require a specific pentest method to be used to meet the objectives defined in the previous step and it might as well require a combination of different methods.

There is value in all methods of pentesting. That said, the recipient must understand the value of each method and it is the pentesters responsibility to help the recipient understand the nuances. I would also include whether the assessment should be performed covertly (low-volume, slow, quiet) versus overtly (high-volume, fast, loud) as this exposes yet further aspects of the security and systems involved. Example: I can throw an off-the-shelf exploit into your network (overt method) or use built-in tools in an attempt to mask my activity (covert method). In either case, if your systems don't identify what was used, even if the attack was unsuccessful, the lack of visibility is a security concern.

In some cases, hiring an external company to do the pentest might be the fastest and easiest way to achieve your objective. Let's also not forget about the security questionnaires that many companies are sending to their vendors as part of the third party risk management programmes - in case of big companies these would very often contain a question about an independent, third party pentest results, which forces the vendors willing to work with them to hire an external pentest provider.

Be it an internal team or an external third-party, what is most important is achieving a balance between in-depth, focused testing and broad, fresh/raw perspective testing. This balance is easiest to achieve in a hybrid of internal and third-party providers, or two third-party assessments with differing familiarity levels. If you're having trouble identifying what works best for you, return to your end-goal objective; why are you getting the pentest in the first place? Ensure you are addressing all your requirements and reach out to someone with more knowledge/experience for guidance if you aren't sure about something.

When choosing a provider, consider not just their expertise and price, but their ethical reputation in the market. A provider with deep access could pose risks if not properly vetted. Additionally, ensure they are updated with the latest attack methodologies and are aligned with prominent standards and frameworks in penetration testing.

Prepare to act upon the findings of the penetration test by establishing a remediation strategy. Include a priority list for addressing vulnerabilities and allocate resources to ensure timely resolution.

In my opinion, preparing an appropriate environment for any penetration testing is the key to a successful pentesting. If you don't possess the requirements, you might miss some of the important parts during the process. Prior to the penetration test, conduct backups of critical data on the target systems. Further to that, If applicable, set up a separate test environment that mirrors the production environment. This allows testers to simulate attacks without affecting live systems. Lastly, Review and update the incident response plan. Ensure that the organization is prepared to respond promptly to any unexpected incidents or issues that may arise during the penetration test.

When prepping for a pentest, assume nothing. Check with all stakeholders and support staff of all the access and credentials can be provided for the specified times, and how quick. Ensure relevant support staff are ready to help troubleshoot access issues. Make sure systems are backed up, just in case!

Ensure comprehensive documentation of all findings, risk levels, and recommended mitigations. Conduct a review meeting with all stakeholders to discuss findings, lessons learned, and future strategies to enhance security posture. Integrate the findings into your ongoing security strategy and ensure necessary mitigations are implemented. Plan for regular re-testing and assessments to validate the effectiveness of the remediation and adapt to evolving threat landscapes.

Do mind that a penetration test can sometimes also (involuntarily) test policies and procedures. If a detection system has failed to detect a penetration test or procedures (after successful detection) were not followed as expected, these are important findings that can be derived from the testing. Penetration testing can therefore not only be about the specific, technical aspect of an individual test, but beyond that, it can also be about validating the overall security framework or the implemented management system for security.

The review of the results of a penetration test is a crucial step in the overall process. Obtain the comprehensive penetration test report from the testing team. This report should detail the findings, vulnerabilities, and recommendations resulting from the test. Secondly, Categorize the findings based on their severity levels. Prioritize critical vulnerabilities that pose the highest risk to the organization. Thirdly, Work with the testing team to understand the root causes of vulnerabilities. Last but not least, Pay close attention to the recommendations provided by the testing team. Evaluate the feasibility and effectiveness of each recommendation in addressing identified vulnerabilities.

If you want to be a safe and risk managing organisation/team, don’t treat vulnerabilities as a blocker and only remediate the necessary, treat them all as a KPI and prioritise using severity. Viewing issues and vulnerabilities in isolation like this does not assess the cumulative risks they pose. To many organisations “only fix highs” before going live, or assigning further budget. Attackers can make use of several medium and low issues to completely compromise a system or service

First of all, implement the remediation plan developed in response to the penetration test findings. Maintain clear and timely communication with stakeholders involved in the remediation process. Validate that the changes made as part of the remediation plan do not introduce new vulnerabilities or negatively impact system functionality. Schedule a retest with the penetration testing team to verify that the remediation measures have effectively addressed the identified vulnerabilities. Establish a feedback loop with the penetration testing team.

Post-pentest actions should be strategic. Addressing immediate vulnerabilities is essential, but also forecast emerging threats and adjust your security posture. Continuous training, drawing from real-life vulnerabilities exposed during the test, can be invaluable. Regularly scheduled pentests should evolve based on prior test findings and changing organizational needs.

Ensure that the right people are available and at the disposal of the testers. Specifically, ensure those people are free from burdens that would make them unavailable! Past reports, policies, unusual/unique solutions and connections present and eliminate the silly gotchas. The testers only have a finite time to conduct the tests and report, give them everything, and make it easy (through paperwork, diagrams, plug-in points) to find their way in! The malicious attackers have far more time to plan and conduct their penetration. Please stop trying to trip up the testers so that you can get a good (but fake good) report.

Prepare for the testers to make best use of their time: - Provide past reports, to retest and validation of controls effectiveness. - Provide an asset inventory, both in/out of scope. This helps everyone tremendously! It helps avoid falling out of scope, and testers do recon too so they can report to you any unknown assets more effectively if they know what to exclude as known. - Provide Attack Surface vulnerability scanner report that is as up to date with triage as possible. Similar to assets, tester's won't waste time on known issues, and can speed run the scenario. Leaving time for the more valuable things that scanners can't do Don't just tell them, show them, get them to validate rather than celebrate pwnage

Pentesting is more than a technical exercise; it's a learning opportunity. Use findings to foster a culture of continuous security awareness and improvement. Collaborate with your pentest provider even post-engagement, sharing feedback and understanding emerging threats. Moreover, always remember that while pentests provide a snapshot of current vulnerabilities, true security is about consistent vigilance and adaptation. By integrating these insights with a structured approach, organizations can ensure that penetration testing serves as an effective tool for enhancing their cybersecurity posture.