What are the most effective strategies for conducting a successful penetration test?

Purpose and objective. What is it wanted to be achieved? This drives the motivation, sourcing method (inhouse, or external consulting) and scoping. Techniques and methods that should be tested. Based on the technology stack, which known techniques must be used? Skills of the testers. How far they're allowed to move or navigate once in. Do we need varity of skills for different tech components? Comms. Timely and effective communication of issues, problems, findings etc. Most importantly, how business would be impacted? What would be the worst case scenario of a specific finding once it was used as a breach point.

Also ensure you get sign off of the requester so that you are not found to be doing an illegal test. Also it helps you in case something breaks during the test..the sign off and scope covered will confirm if you went out of scope or not

Using pen test results to secure your SDLC and your code You can use pen test results in various ways to secure your SDLC as well as your code. Policy and standards: Update your policy and standards to explicitly state that production defects are not tolerated, and fund efforts for training, tooling, and prioritizing defect detection and remediation. Senior leadership can approve and enforce policy and standard changes based on pen test results. Requirements: Start writing reusable, implementable, and testable security requirements that address the OWASP Top 10 vulnerabilities. When pen tests detect security defects, write user stories and approval criteria to prevent those defects .

¬The environmental context is pivotal in delineating the objectives and scope of a project. An exhaustive analysis of the intended system is crucial to tailoring a strategy that is optimally suited to the specific configuration. Consequently, the penetration testing protocols for a Hospital Medical System must inherently differ from those applied to a University Network due to their distinct operational environments.

It's beneficial to articulate the scope and goals in a detailed document, often referred to as the Rules of Engagement, which should be reviewed and approved by all relevant stakeholders. This document ensures that every participant understands the limits of the testing and the key objectives. Additionally, clearly defined goals, such as identifying data exfiltration paths, testing incident response effectiveness, or validating security controls, help in measuring the success of the penetration test against quantifiable outcomes.

selecting the appropriate technique black, gray etc... for the assessment should be part of the scoping. Initial knowledge of this will be crucial in selecting the appropriate tools and other factors.

Penetration testing (pen test) tools and techniques are vital for discovering and mitigating vulnerabilities in systems and networks. Here are some widely recognized tools and techniques: **Pen Test Tools:** 1. Metasploit 2. Nmap 3. Wireshark 4. Burp Suite 5. OWASP ZAP 6. Nessus 7. Aircrack-ng 8. John the Ripper 9. SQLmap **Pen Test Techniques:** 1. Reconnaissance 2. Scanning 3. Vulnerability Assessment 4. Exploitation 5. Post-Exploitation 6. Reporting

Tools to be used and kinds of test to be done and approach may be influenced the kind of environment you are testing. OT environments does not respond the way an IT will. So lots of considerations around this as well

Careful planning, technical expertise and an in-depth knowledge of the target system or network are all important for a successful penetration test. Here are some strategies that can work for a successful penetration test: Define Clear Objectives: Outline clearly the objectives and scope of the penetration. Understand what the institution wants to achieve and identify specific targets or systems that require testing. Gain Authorization: Acquire proper permission from the organization before conducting any penetration testing. Unauthorized testing may cause legal implications.

It is important to acquire the proper tools for the scope of the pentest. If specific licences need to be acquired, they should be included in the scope of work and the quote or budgeting part of the proposal.

From experience, penetration testing involves more than just running automated tools in succession and producing technical findings. It ought to include precise instructions on how to defend against actual attacks on an organization's data and information systems. The underlying methodology of penetration testing is one important component in its effectiveness. To successfully document a test and provide reports targeted at various organisational management levels, a methodical and scientific methodology should be employed. To allow the tester to thoroughly investigate his intuitions, it shouldn't be too limiting. Test preparation, the actual test, and test analysis are the three stages that typically comprise penetration testing.

Actually regular engagements will validate if you are proceeding in the right direction or not. It will also determine if there are specific areas of focus the client would want more efforts to be deployed

For effective communication and collaboration during penetration testing, teams often use a combination of tools and platforms tailored to the needs of security professionals. Here’s a list: Communication Tools: 1. Slack 2. Microsoft Teams 3. Discord 4. Wire 5. Signal 6. Telegram Collaboration and Project Management Tools: 1. Trello 2. Jira 3. Confluence 4. GitLab 5. GitHub 6. Mattermost 7. Basecamp 8. Asana 9. Redmine 10. Dradis

I think communication during penetration tests should be very simple and straightforward. IT professionals we sometimes talk above the head of the business and this hinders objectives of the processes. Tooling should be to simplify that process significantly

The “Measure and Report” technique in cybersecurity, as outlined by organizations like SANS and CIS, is about quantifying security posture and conveying that information effectively to stakeholders. Here’s how it is typically approached: 1. Define Security Metrics 2. Data Collection 3. Analysis 4. Benchmarking 5. Reporting 6. Dashboarding 7. Regular Review 8. Adjust and Act 9. Compliance Reporting 10. Continuous Improvement

Both blue teams and red teams should reflect on what went wrong, what could be improved about the operation and how the security of the network or infrastructure could be improved

The goal is not just to find vulnerabilities but to enhance an organization's security. Adaptability is crucial. Successful penetration testing involves a structured approach with key strategies: 1. Set clear objectives. 2. Research the target thoroughly. 3. Obtain legal authorization. 4. Define the scope. 5. Choose a methodology. 6. Use automated tools for vulnerability assessment. 7. Conduct manual testing for complex vulnerabilities. 8. Attempt exploitation carefully. 9. Test for privilege escalation if relevant. 10. Document findings. 11. Create a comprehensive report. 12. Provide remediation support. 13. Continuously improve your methodology. 14. Maintain open communication. 15. Adhere to legal and ethical standards.

Clearly outline the goals and scope of the penetration test. Identify specific systems, networks, or applications to be tested, and define the desired outcomes.

Obtain a clear target or list of targets from the client, assess the risks and clarify any legal issues. During the testing phase, thorough reconnaissance on the target is the next important step. Then the findings from the reconnaissance stage can be used to further test the target asset in a particular direction.