Interview questions for Penetration testing

The team’s primary goal is to launch just about any kind of attack that is imaginable in an effort to discover any unknown security gaps and weaknesses. Their findings are then summarized into a comprehensive report, supported with solutions as to how these vulnerabilities can be fixed.
Because of the dynamic nature of the cyber-threat landscape, the demand for pentesting is quite high, and is expected to be so into the coming future.
Becoming a penetration tester requires a mixture of both quantitative and qualitative skills. For example, he or she has to decipher the complex reports that are output by the pentesting tools, as well as having the patience to work very long hours and at odd times.

1. Could you describe information security?

As penetration testing is part of a company’s security strategy, interviewers may want to know about your general knowledge of the field. Consider describing any components of information security and how organizations use it.
Information security is how companies protect their systems and information from threats. It can include the processes an organization follows to ensure security, the technology infrastructure and the roles that govern this area.”

2. What is pentesting in your own words?

Interviewers might want you to describe your own definition of pentesting to learn your understanding of this process. You can provide a basic summary of this process and how it supports an organization’s security goals.

Pentesting is a type of testing that companies use to identify and prevent any security threats. Through several methods, this helps organizations proactively manage risks in their systems, networks and programs.”

3. What is a specific definition of pentesting?

Let’s ask the people in the know. Cloudflare.com says the following: “Penetration testing (or pentesting) is a security exercise where a cybersecurity expert attempts to find and exploit vulnerabilities in a computer system. The purpose of this simulated attack is to identify any weak spots in a system’s defenses which attackers could take advantage of.”

4. What is the primary purpose of pentesting?

The main purpose of a pentest is to conduct a “deep dive” into the IT Infrastructure of a business or a corporation with the primary intention of gaining access to any (and if possible, all) of the electronic based assets that exist. It is important to note that the goal of the pentester is not to attempt to strike a hard blow right at the very beginning; rather, they escalate the intensity of the cyber-attack over a period of time.

5.What are the goals of conducting a pentesting exercise?

The goals are as follows:
• To test adherence to the security policies that have been crafted and implemented by the organization
• To test for employee proactiveness and awareness of the security environment that they are in
• To fully ascertain how a business entity can face a massive security breach, and how quickly they react to it and restore normal business operations after being hit.

6. What are the different penetration phases?

Hiring managers may ask about your involvement with the different phases of pentesting. As each might require specific expertise, you can provide a brief overview of each. If you tested in any of these phases, consider mentioning your experience.
Example: “The five phases in pentesting are reconnaissance, scanning, gaining access, maintaining access and covering tracks. The first is where you pose as the hacker to gain information about a company, like its IP address. Scanning identifies potential ways they can hack into a company. Gaining and maintaining access means breaching any systems and extracting data while in, and covering tracks means the tester removes logs and other evidence that they accessed a system. At my previous job, I primarily performed the first two phases by using a third-party account to gather vulnerability information for our company.”

7. What are the different encryption types?

As encryption is a common way for organizations to protect their data, hiring managers might ask about these different methods. Providing a brief definition and how you might use each can show your encryption knowledge.
Example: “Symmetric and asymmetric encryption are the two main types. Using keys, symmetric encryption means users and information owners can use the same key to encrypt or decrypt information. Assymetric means there’s a private and public key to increase data protection for more sensitive information.”

8. What’s your process when pentesting?

This question tells interviewers how you apply the standards of pentesting with your own process. Consider explaining the steps you take to prepare for a new test, techniques you use, the tasks you perform and how you complete testing.
Example: “First, I evaluate the software that requires testing to decide which technique to use. In my previous role, I primarily performed web application testing, where I would spend a lot of time with reconnaissance and scanning to identify any vulnerabilities. Once complete, I’d investigate what data was vulnerable and try to hack as much as possible. With this information, we could decide on the risk level and implement security measures.”

9. Have you used different pentesting methodologies?

Certain companies may require different methods of testing, where they provide a certain amount of information to a tester. Consider mentioning each method, and with which you have experience. Familiarity with black-box testing can show your expertise in pentesting.
Example: “I’ve used all three methodologies, black-box, white-box and gray-box testing. We mostly performed gray-box testing for our legacy systems with many security controls, but I often performed black-box testing with no prior knowledge for new software applications.

10. Are Denial-of-service Attacks Also Tested?

Denial-of-service (DoS) attacks are usually only examined if it seems to be possible to put a system’s availability at risk with very small effort. This can for example be a misconfiguration or a program error (say, if a system crashes when it gets sent an overly long request). Attacks like this will only be performed after an explicit agreement is provided, to verify if the attack is indeed possible.
On the other hand, attacks that try to saturate the bandwidth a company has at its disposal are usually not tested, as this is always possible for attackers with sufficient resources and will also affect third-party systems. Distributed denial-of-service attacks, that usually involve hundreds, if not thousands, of zombie systems (systems that were compromised and can now be remotely controlled) cannot be simulated realistically.

11. Does Redteam Pentesting Do Social Engineering?

Penetration tests may include social engineering techniques. These techniques are not without controversy though. More detailed information about the problems occuring with social engineering and penetration tests is available under exploitation. One safety measure against social engineering attacks can be trainings for your employees.