This entry was posted in and tagged on by Guest Contributor: Penetration Tester I spent quite some time trying to figure out the answer to this question when I created my online training with the clever title ““. In this post I will try to summarize what I learnt when I looked at my own career and what we look at when we hire new people to my team.

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Process Since this post is about ‘ how to become a web pentester‘ first I wanted to give an overview of the process that I find most efficient: • Establish a security mindset • Acquire technical knowledge • Learn attack techniques • Acquire social skills • Create proof-of-knowledge Let’s go through these points one by one. Security Mindset One thing that is probably more important then the technical knowledge is what I call here ‘security mindset’. This is a point of view or way of thinking. Most of the people that work in IT security don’t necessarily have technical knowledge, but they have a security mindset. This means that they can look at systems, and more broadly the world, in a critical way that helps identify things that can go wrong or can be maliciously exploited. I originally worked as a normal software tester, and if you read any book about testing, it will have a chapter called the “Psychology of Testing”. This chapter will tell you that while a developer’s goal is to write good code, the tester’s goal must not be to prove that the code is bug free.

The tester’s goal must be to find bugs. Because if he tries to prove that the code does not have bugs, then he will never have success. The tester must train himself to be happy when he finds a bug.

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Because otherwise he will unconsciously not test things that might actually fail. This is, for instance, why developers shouldn’t test their own code, because they want it to work. But the tester wants it to break, so they will test the code with the meanest tests. This is the same with security but instead of just focusing on functionality problems one needs to keep security in mind. How could this system be cheated? How can be a protection bypassed? What data is confidential and how can I access it?

You need to develop this constant assessing mindset where you always look for things that could go wrong. How to learn it: You can consciously train your mind for this. Wherever you go in the world try to look for security weaknesses. It doesn’t have to be computer systems, it could be anything, for instance: • You fly somewhere and pay attention whether your identity is checked at all while you get to the plane.

Sometimes they check you many times but only your boarding pass and never your ID. • You go to concert and you notice that there is a door where nobody checks the ticket.

• When you go to a cinema your ticket is checked but not invalidated, so with 2 tickets you could bring in as many people as you want. Technology Obviously big part of pentesting is technical skills. However this is something that you will never stop learning. There will be always new tools, new frameworks. I think the goal here is to get the basics and keep developing yourself as you work. Here is what I think is the basics: • HTTP: You need to understand the HTTP protocol, how requests are sent to the server and how responses are sent back.

Fortunately HTTP is fairly simple so this shouldn’t be difficult. • SSL: since it is used in HTTPS, it is good if you understand how it works.

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