How do you align your security goals with penetration testing?

1. Identifying scope for pen testing requires systematic approach. It starts with - Why am I pen testing ? - If its for compliance - scope at a min would include those critical apps/ systems, processes, people processing sensitive data. - If its for improving security posture - include comprehensive approach such as web pen test, network /infra pen test etc . 2. For all good reasons, pen test should be performed after signing clear NDA, approval and agreement on assets under scope with clear deadlines. 3. Agree on methodology - white / black / grey 4. Don't forget to agree on reporting formats too as they are key artefacts. 5. As an organization- define clear approach. Don't perform intrusive pen tests on production systems

In my opinion, setting a well-defined scope is essential before starting penetration testing. According to me, this means outlining the systems, networks, and methods you'll use, while considering legal and ethical concerns. Clearly defining your scope helps focus your testing efforts and ensures adherence to standards.

While implementing firewalls, encryption protocols, and intrusion detection systems are crucial, they don't provide a complete picture of an organization's security posture. This is where penetration testing steps in - a proactive and dynamic approach that helps align security goals with real-world scenarios.

In my opinion, once you've outlined your scope, it's essential to define precise objectives for your penetration testing. According to me, these objectives should be SMART: Specific, Measurable, Achievable, Relevant, and Time-bound. By aligning with your security strategy and meeting organizational needs, clear objectives help you prioritize tasks, allocate resources, and demonstrate your impact.

In my opinion, setting up the objectives not only guide the process but also imbue it with purpose. Targeted assessments reveal application weak spots, while evaluating incident response effectiveness casts a wider net, assessing coordination, efficiency, and damage control. By aligning testing with objectives, organizations navigate the complex landscape of security with clarity and purpose.

In my opinion, the following task is to decide on your penetration testing approach. According to me, this involves choosing how to simulate the attacks you wish to test, considering options like black box, white box, or gray box testing based on your access level to the target system. This approach helps align your scope, objectives, and tool selection effectively.

In my opinion, when determining your goals, the selection of a penetration testing approach takes center stage. Among the alternatives—black-box, white-box, and grey-box methodologies—each carries unique merits. Your chosen approach should harmonize with your objectives and offer the utmost accuracy in portraying potential vulnerabilities.

Selecting and/or creating your tools is dependent on your targets in scope. A short overview of tools I’ve used: Recon: asset finder, crt.sh, OWASP amass, Wappalyzer, and wfuzz are good tools to enumerate a target web app. Combining bash scripting can help automate recon and scanning. Scanning: Nmap for port and service version information, Burpsuite, Nikto and Nessus scanners for common web application vulnerabilities Exploitation: msfvenom for payload generation and encoding, Metasploit exploit modules for convenience, publicly available exploit POCs on exploit database, searchsploit, and GitHub. Post exploitation: winpeas and linpeas for privilege escalation paths, kerberoasting in AD environments, impacket Python library.

Selecting the right tools for penetration testing is crucial. These tools, such as Nmap, Metasploit, Burp Suite, Wireshark, and Kali Linux, aid in executing the different stages of testing effectively.

Tools are the building blocks of penetration testing. Whether you're focused on network vulnerabilities, web applications, or social engineering, having the right tools at your disposal is essential. The tools you select should align with the technologies and systems you're testing and be updated to cover the latest threats.

Once the groundwork is laid, it's time to execute the penetration testing. Skilled testers simulate real-world attacks, attempting to exploit vulnerabilities just as malicious hackers would. This step is where the rubber meets the road, providing insights into an organization's defense mechanisms and potential weak points.

In my perspective, the final step is executing the penetration testing aligned with my scope, objectives, approach, and selected tools. This demands applying my skills to identify and exploit vulnerabilities, and documenting findings in a report for stakeholders. This phase showcases my abilities, delivers value, and bolsters security measures.

After conducting the tests, it's imperative to review the results in detail. Identify the vulnerabilities that were successfully exploited and those that were effectively mitigated. This review process is not just about identifying weaknesses but also about learning from them to enhance your security measures.