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Table of Contents
1. What is penetration testing?
The penetration test is a simulated cyberattack on a network, system, or application to evaluate its security. The goal of penetration testing is to find the potential weaknesses and how you might hack the site before the bad guys can. This means systematically looking for vulnerabilities and reporting back with findings for treatment.
2. Why is penetration testing important for a software company?
When it comes to risks, penetration testing offers the opportunity to uncover vulnerabilities in software to avoid data breaches, service interruptions, and the headache of non-compliance. For software vendors, it guarantees product cleanliness and user confidence, which is particularly critical for systems containing sensitive data or when services are offered to external clients.
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3. What are the main phases of a penetration test?
A penetration test, as it may be performed using the industry standard model, is generally composed of 5 phases: 1- Reconnaissance, 2- Scanning, 3- Gaining access, 4- Maintaining access, 5- Analysis and reporting. Each stage evolves to the next one, emulating a real attack pathway while generating a detailed security report.
4. What is the difference between vulnerability assessment and penetration testing?
Vulnerability assessment looks for known vulnerabilities using automated tools, while penetration testing attempts to exploit those vulnerabilities to see what the actual risk is. Penetration testing is more thorough and emulates an attacker who can have the same approach.
5. What is the difference between black-box, white-box, and gray-box testing?
Black-box testing is performed without knowing how the system is functioning. White-box testing grants access to code and architecture. Gray-box testing offers partial insight. Both models represent different attacker motivations and have different advantages.
6. Which tools do you commonly use in penetration testing?
The common tools include Nmap, which is used for network mapping; Burp Suite for web app testing; Metasploit for exploitation; Nikto for web server scanning; and Wireshark for packet analysis. These are just a handful of the commonly used tools that come to mind. The selection depends on the scope and goals of the test.
7. What is Metasploit, and how do you use it?
Metasploit is a penetration testing framework that makes it easy to write and execute exploit code against a remote target machine. I use it for scanning, creating a payload, and auto-exploitation during internal and external infrastructure tests.
8. What is the OWASP Top 10?
The OWASP Top 10 is a list that is regularly updated and shows you the most critical web application security risks. Its threats include areas such as injection, broken authentication, and cross-site scripting (XSS). It serves as a pointer for developers and testers, indicating where to focus.
9. Explain SQL injection and how you would test for it.
SQL injection is a security vulnerability that allows malicious users to interfere with an application’s requests to its database. So I test for it by feeding crafted inputs into user fields to see if I can manipulate the database or extract unauthorized data.
10. What is cross-site scripting (XSS), and how do you detect it?
XSS enables attackers to inject client-side scripts into web pages viewed by other users. I test whether XSS is possible by inserting script tags into the input fields and checking if the browser executes them (if it does, it means they are not properly sanitized).
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11. What is the purpose of a payload in a penetration test?
The payload is the piece of the exploit that does the magic on the target, like popping a reverse shell or elevating the user’s rights. It comes after a vulnerability is exploited to take control or scoop up data.
12. How do you perform privilege escalation?
Privilege escalation means finding a misconfiguration or a hole in security to get higher rights. I will search for hardcoded credentials, writable paths, outdated software, or weak permissions to get my escalation vectors.
13. How do you remain stealthy during an engagement?
I use low and slow scanning techniques and don’t do anything noisy like reverse. I cycle out IPs with proxies and have SSL from my scraper to my storage system. A product needs to be stealthy so that the real-world attacker will not get alerted.
14. What’s the difference between TCP and UDP scans?
TCP scans are connection-oriented and somewhat reliable; UDP scans are connectionless, more difficult to detect, and less informative. I will select a scanning method that is appropriate to the scene and the purpose of the inspection.
15. How do you identify and exploit open ports?
I start with tools like Nmap to find open ports and then find the services running on those ports. I find out about known vulnerabilities or misconfigurations in those services, and then I write custom exploits or use prebuilt ones from a framework like Metasploit.
16. What is lateral movement, and why is it important?
Lateral movement refers to when an attacker moves from system to system across a network after a successful initial breach. It can reveal the extent of what an attacker would be able to accomplish and expose holes in internal segmentation or access control.
17. How do you approach testing APIs?
I test APIs by analyzing endpoints, reviewing request methods, and checking for improper authentication, input validation, or sensitive data exposure. Tools like Postman and Burp Suite help automate and monitor API interactions.
18. What is a buffer overflow, and how do you test for it?
Buffer overflow, being the most common type of overflow, occurs when memory data exceeds its allowable capacity and may be hijacked to run, infecting the host with malicious code. I find it by typing in large strings to see if behavior changes or it crashes—usually in compiled programs or embedded systems.
19. How do you handle the scope and rules of engagement?
Before administering a test, I articulate what is in and out of scope — what systems are, and are not, in scope — as well as the techniques and timing that are fair game. This maintains the legal and moral lines we won’t cross while enabling us to help manage your expectations and your risk.
20. What’s your process for reporting findings?
I report every discovery with a detailed explanation, CVSS score, reproduction steps, screenshots, and recommendations. I focus on high-impact bugs and report in a way that is clear for technical people and also the executive board of a company.
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21. How do you stay updated with the latest security threats?
I subscribe to reliable sources like HackerOne, Exploit-DB, as well as security researcher blogs. I go to conferences and try new tools in lab settings all the time, so I can pick up different attack methods and targets.
22. How do you test mobile applications?
I leveraged tools such as MobSF and Burp Suite to dissect APK files, analyze the traffic to the service, and search for insecure storage, insecure login, and code obfuscation issues. I do reverse engineering and simulate attacks on mobile APIs.
23. What steps do you take after discovering a critical vulnerability?
I report it immediately via the agreed reporting channel, explain in detail, and recommend emergency mitigations. I then help the development and security team reproduce and patch the issue.
24. How do you handle false positives?
I don’t just parse/bounce from automated tools; I level check—for real impact, real exploits, by hand. A false positive is excluded from the final report when rigorously validated to ensure accuracy and trust.
25. How do you prioritize vulnerabilities during an assessment?
I evaluate according to exposure, exploit, business impact, and ease of remediation. In any software release, real-world, critical flaws that have an active attack vector take precedence over high, medium, and low-severity flaws.
26. What experience do you have with social engineering?
In permitted scenarios, I simulate phishing attacks or impersonate internal users to test employee security awareness and organizational readiness. With social engineering, we can see the weakness of the human element in security.
27. How do you test for insecure configurations?
I review system configurations, file permissions, patch status, and default credentials. There are tools like Lynis and CIS benchmarks to benchmark systems against security best practices. In many cases, misconfigurations open the door to simple hacks.
28. What’s the most challenging penetration test you’ve conducted?
In the past, I tested a highly segmented financial app with multi-factor authentication and other hardcore time windows. Deep coordination, custom payloads, and scripting were needed to work around limitations, so it was a much more valuable and complex engagement.
29. How do you ensure your tests don’t cause system downtime?
I test in a controlled manner, with no destructive payloads, read-only during the scan, and keep real time communicaton with system owners. I’ve used maintenance windows to also schedule tests if necessary, etc.
30. How do you demonstrate ROI for penetration testing?
By demonstrating how vulnerabilities could lead to real damage—think data leaks or financial loss—and measuring how much the risk was reduced after they were fixed. I also map investigation results to compliance and business impact.
Conclusion
Mastery in these 30 interview questions is important to enter its next penetration tester role in a software company. Whether you are preparing for a technical interview or the manager who refines your selection process, these insights are your roadmap. Stay sharp, be moral, and continue searching for the world that sometimes develops moral hacking. Want more resources? Subscribe to our newspaper for the latest in cybersecurity careers.
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