Offensiveinterview
Interview questions to screen offensive (red team/pentest) candidates
Install / Use
/learn @WebBreacher/OffensiveinterviewREADME
Purpose
Collect a large sampling of interview questions to screen offensive (red team/pentest) candidates
If you are a candidate and looking to find some good questions to ask employers, visits @doctorj's page here: https://gitlab.com/doctorj/interview-questions/blob/master/interview-questions.yml
Contributing
- Use the standard method of forking this repository, making your changes and doing a "pull" request to have your content added
- Format your questions as a numbered list, the question, your name (@name) if you'd like attribution, then any directions for the interviewer in italics. These are directions on what to look for or how to ask the question not answers to the questions.
- Examples:
- "What is CSRF and how is it different from XSS?" @webbreacher
- "I have a /24 subnet on the Internet. You are a pentester. Tell me, start to finish, how you would execute this assessment." @webbreacher Look for everything from scoping meeting and rules of engagement to the depth/detail of their responses.
- Alternatively, if you just want to copy/paste your content, we'll take that too! Create an "Issue" with your content and we will add for you. Please tell us if you'd like attribution ("this question came from @johndoe") or not.
Organization
Questions should be organized (right now at least) in a couple different formats:
- Open-ended Questions
- These questions have multiple methods of achieving a "correct" response.
- Examples:
- "Describe how you would compromise a victim's laptop using a phishing attack."
- "What would you do once you successfully got a shell on a database server?"
- Knowledge-based Questions
- There is a specific right and wrong answer for these questions.
- Examples:
- "What is CSRF and how is it different from XSS?"
- "What are the primary differences between
netcatandncat?"
- Scenario-based Questions
- These questions are ones in which the interviewer sets up a situation and allows the candidate to respond. During their responses, the interviewer adds (more information | emulates a client | tells the candidate what happens when they take an action) in order to more fully understand the breadth and depth of a candidate's knowledge.
- Examples:
- "I have a /24 subnet on the Internet. You are a pentester. Tell me, start to finish, how you would execute this assessment."
- "You have just compromised a Mac OS X laptop inside a corporate user subnet. Your goal is to exfiltrate Active Directory hashes. How do you accomplish this?"
- Other Questions
- These questions do not fit in the other categories.
- Examples:
- Right now I have no examples of this but you may!
Chinese Translation
If you would like to read a Chinese translation of this project, visit https://github.com/Leezj9671/offensiveinterview.
License
<a rel="license" href="http://creativecommons.org/licenses/by-sa/4.0/"><img alt="Creative Commons License" style="border-width:0" src="https://i.creativecommons.org/l/by-sa/4.0/88x31.png" /></a><br />This work is licensed under a <a rel="license" href="http://creativecommons.org/licenses/by-sa/4.0/">Creative Commons Attribution-ShareAlike 4.0 International License</a>.
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Security Score
Audited on Mar 31, 2026
