Breaking into web pen-testing

Welcome to this technical guide for beginners interested in web hacking and bug bounty. In this post, we will provide you with the necessary information and tips to get started in this field. Whether you are a beginner or an experienced professional looking to improve your skills, this guide aims to provide valuable insights and resources to help you succeed. So that being said, let’s get started!

BACKGROUND

Web penetration testing, also known as web application testing, is the process of simulating unauthorised attacks on a web server to identify vulnerabilities and access sensitive data. It helps end-users determine the security of their email servers, web servers, and data, as well as the likelihood that a hacker could gain access to it through the internet. This process involves simulating attacks from both internal and external sources in order to test the security of the system and identify potential weaknesses.

Main objectives of web penetration testing include:

Identifying software flaws, operational weaknesses, and sensitive information leakage: A web penetration tester’s primary goal is to identify any vulnerabilities or weaknesses in the system that could potentially be exploited by a hacker. This includes identifying software flaws, operational weaknesses, and sensitive information that may be at risk of being leaked.

Providing recommendations and remediation support: After identifying vulnerabilities, a web penetration tester will typically provide recommendations for how to fix them and improve the overall security of the system. This may include providing remediation support to help implement the necessary fixes.

Identifying improper or poor configurations: Web penetration testers may also identify improper or poor configurations that could potentially compromise the security of the system. This could include identifying insecure configurations or misconfigured security settings that may leave the system vulnerable to attack.

Why web penetration testing is important:

Ensuring that security mechanisms in web applications are properly implemented: Web penetration testing helps to ensure that the security measures in place to protect web applications are properly implemented and effective at preventing unauthorised access.

Preventing data breaches: By identifying vulnerabilities and weaknesses in a web application, web penetration testing can help prevent data breaches that could potentially result in the loss or theft of sensitive information.

Determining the feasibility of attack vectors: Web penetration testing helps to determine the feasibility of different attack vectors that could potentially be used to compromise the security of a web application. This helps organisations to better understand the risks they face and take appropriate measures to mitigate them.

Raising awareness among IT staff: Web penetration testing can help raise awareness among IT staff about the importance of web application security and the potential risks associated with ignoring it.

Ensuring compliance with industry standards and laws: Web penetration testing is also important for ensuring that web applications are compliant with relevant industry standards and laws, such as the Payment Card Industry Data Security Standard (PCI DSS). This helps organisations to avoid costly fines and legal issues that could arise as a result of non-compliance.

Why you might consider becoming a web penetration tester:

Legal hacking: As a web penetration tester, you get to explore the world of hacking and cybersecurity, but in a legal and ethical way. This allows you to use your skills and knowledge to help organisations improve their security without breaking the law.

High pay: Web penetration testing is a lucrative field, with many professionals earning a high salary for their skills and expertise.

Cool information security job: Web penetration testing is widely regarded as one of the coolest jobs in the field of information security. If you’re passionate about cybersecurity and enjoy problem-solving, this could be an ideal career path for you.

Understanding how systems can be penetrated: By becoming a web penetration tester, you’ll gain a deep understanding of how systems can be compromised and what steps organisations can take to prevent these attacks. This knowledge can be valuable for your own personal security as well as for helping others to protect their systems.

Tips for self-study in web penetration testing:

Find a mentor: Having a mentor can be incredibly valuable when it comes to learning and improving your skills in web penetration testing. A mentor can provide guidance, answer your questions, and offer valuable insights based on their own experience in the field.

Use Google: Before asking for help, try to figure out the answer on your own by using Google. This will save you time and help you develop your problem-solving skills.

Ask questions in a professional manner: When seeking help, be sure to ask your question in a professional manner. Avoid phrases like “Please help me hack this,” as this is rude and unprofessional. Instead, try to be specific and provide details about what you’re trying to do and any errors or issues you’re experiencing.

Develop key characteristics: In order to succeed in web penetration testing, it’s important to cultivate certain characteristics such as curiosity, a desire to learn on a daily basis, good communication skills, and the ability to handle failure.

Build an offensive mindset: As a web penetration tester, you need to think like an attacker in order to find vulnerabilities and weaknesses in a system. This requires an offensive mindset and the ability to think creatively about how to test the system.

Stay up-to-date: In the fast-paced world of cybersecurity, it’s important to stay up-to-date on the latest trends and techniques. Following industry leaders on Twitter or subscribing to newsletters can help you stay informed and improve your skills.

Building Your Skills

Operating Systems

As a web penetration tester, it’s important to have a strong understanding of operating systems, particularly those in the Windows and UNIX families. This is because many web servers run on Linux, and you may encounter these systems during your work as a tester.

In order to be proficient in both Windows and UNIX systems, you should have a good understanding of basic commands, directory and file structure, configuration files, and system administration. It’s also helpful to be familiar with different system models, such as client-server and peer-to-peer.

Additionally, many hacking tools are only available for Linux systems, so having a solid understanding of this operating system is essential for any web penetration tester. Some of the basic tasks you should be able to perform include navigating the file system, editing configuration files, and performing basic system administration tasks.

Overall, having a strong understanding of operating systems is an important skill for any web penetration tester to have in their toolkit.

Network infrastructure and protocols

As a web penetration tester, it’s important to have a solid understanding of network infrastructure and protocols. Some key things you should understand include:

Web application architecture: Understanding the architecture of web applications is essential for identifying vulnerabilities and weaknesses. This includes understanding how different components of the application interact with each other and how data is transmitted between them.

Network protocols: Familiarising yourself with protocols such as HTTP, HTTPS, SMTP, SSL/TLS, TCP/IP, and ARP can help you understand how data is transmitted over networks and how to identify potential vulnerabilities.

Network appliances: Understanding network appliances such as firewalls, load balancers, web application firewalls, and IDS/IPS systems can help you identify and exploit vulnerabilities in these systems.

Overall, having a strong understanding of network infrastructure and protocols is essential for any web penetration tester. By familiarising yourself with these concepts, you’ll be better equipped to identify vulnerabilities and weaknesses in web applications and networks.

Programming skills

While programming skills are not strictly necessary for web penetration testing, having a basic understanding of programming can be very beneficial. This is because programming knowledge can help you understand how web applications are built and how they function, which can make it easier to identify vulnerabilities and weaknesses.

Here are some programming languages that you might want to consider learning as a web penetration tester:

  • Client-side languages: These are languages that are run by a web browser and include HTML and JavaScript.
  • Server-side languages: These are languages that run on servers and include PHP, Java, Flask, and Node.js, among others.
  • Scripting languages: These are languages that are used to automate tasks and include Bash, Python, Ruby, and Perl.
  • Query languages: These are languages that are used to access and manipulate data stored in databases, and include SQL, Xpath, LDAP, and NoSQL database programs such as MongoDB.

Learning one or more of these programming languages can help you better understand how web applications work and improve your skills as a web penetration tester.

Basic hacking skills

If you’re interested in getting started in web penetration testing, there are many resources available to help you learn and improve your skills. Some of the options include:

Online training platforms: There are many online platforms that offer training in web penetration testing, such as Portswigger and Pentester Lab. These platforms provide a variety of resources and challenges to help you learn and practise your skills.

Virtual labs: You can set up your own virtual lab to practise web penetration testing in a safe and controlled environment. Metasploitable3 is a popular tool for creating a virtual lab, and there are also many other options available.

To set up your own hacking environment or virtual lab for web penetration testing, you’ll need a laptop with certain specifications to ensure that it can handle the demands of running multiple virtual machines (VMs).

Here are some recommendations for what you’ll need:

  • A laptop with at least 8 GB of RAM: This will ensure that your laptop has enough memory to run multiple VMs without experiencing performance issues.
  • An i7 Intel Quad-Core processor: This will give your laptop the processing power it needs to handle the demands of running multiple VMs.
  • 500 GB of hard drive space: You’ll need plenty of storage space for your VMs and any tools or resources you’ll be using. It’s best to use a solid-state drive (SSD) if possible, as these tend to be faster and more reliable than traditional hard drives.

VMware Workstation, Fusion, or Player: These are all popular tools for creating and managing VMs. You can choose the one that best suits your needs and budget.

Once you have these requirements met, you can create your own virtual lab using tools like Metasploitable3 (https://github.com/rapid7/metasploitable3). This is a pre-configured Linux VM that is designed specifically for practising web penetration testing and is widely used by professionals and beginners alike.

Sharpen Your Skills And Level Up

There are several ways to improve your skills and level up as a web penetration tester. Here are some suggestions:

Read blogs: There are many blogs and online resources that cover topics related to web penetration testing. Reading these can help you stay up-to-date on the latest trends and techniques, and provide valuable insights and tips for improving your skills.

To stay informed about the latest trends and techniques in web penetration testing and improve your skills, consider following some of these blogs written by experts in the field as a start:

  • Techvomit
  • Skeleton Scribe
  • Pentester Land
  • Shawar Khan
  • Footstep Ninja
  • ZSec UK
  • Wareeqshile

By bookmarking these blogs and checking for updates regularly, you can stay up-to-date on the latest developments in the field and improve your skills as a web penetration tester.

Follow industry leaders on Twitter: Many experts in the field of web penetration testing are active on Twitter, and following them can help you stay informed about the latest developments and opportunities to learn.

Twitter is a great resource for staying up-to-date on the latest trends and techniques in web penetration testing and improving your skills. Here are some Twitter accounts that you might find helpful to start with:

By following these accounts, you can stay up-to-date on the latest developments in the field and improve your skills as a web penetration tester.

Participate in Capture the Flag (CTF) challenges: CTF challenges are a great way to practise your skills and compete with other testers. Many organisations and communities host CTF events, so be sure to check out what’s available in your area.

Capture the Flag (CTF) hacking is a great way to learn and improve your skills in web penetration testing. In a CTF event, participants compete to solve challenges related to computer security, often involving web application security. Here are some resources that you might find helpful for participating in CTFs:

By participating in CTF events, you can gain practical experience in solving real-world security challenges and improve your skills as a web penetration tester.

Join a bug bounty program: Bug bounty programs are a great way to practise your skills and get paid for finding vulnerabilities in real-world systems. Many companies and organisations offer bug bounty programs, so be sure to check out what’s available and consider joining one.

Overall, staying active and engaged in the field is the best way to improve your skills and level up as a web penetration tester

CONCLUSION

In conclusion, web penetration testing is a valuable skill that can help identify vulnerabilities in web applications and prevent data breaches. As a web penetration tester, your goals may include identifying software flaws, operational weaknesses, and sensitive information leakage, providing recommendations and remediation support, and identifying improper or poor configurations.

To improve your skills in web penetration testing, it’s important to find a mentor, educate yourself on a daily basis, and have strong communication skills. Building an offensive mindset, staying up-to-date, and participating in CTF events and bug bounty programs can also be helpful in improving your skills.

Keep in mind that it can take some time and effort to become proficient in web penetration testing, but the rewards can be well worth it. It’s a challenging field, but by being curious, obsessed, and hacking more, you can develop the skills you need to succeed as a web penetration tester.