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Thinking Outside the Box: A Pentester’s Mindset




 What is Pentesting?

Penetration testing, or “pen testing” is like being a good hacker to help protect a company’s computer systems. It’s about trying to break into these systems in a safe way to find weaknesses before the unethical hackers do. The act of pen testing plays an important role in keeping the company’s information safe.


But sometimes, people doing pen testing just follow a simple list of steps or use the automated techniques that help them in checking. While it might be helpful, they can’t always find the trickier ways that hackers might get in. That’s why pen testers need to think creatively and be ready to change their plans, just like hackers can do.


Thinking like a hacker means looking for all the different ways someone could try to break in, not just the easy or obvious ones. It also means thinking about how people might accidentally make it easier for hackers, like being tricked into giving away passwords.


In this article, we talk about why it’s so important for pen testers to have this creative and flexible way of thinking. To protect against hackers, pen testers need to be one step ahead, using their skills to find weaknesses that the automated techniques might not catch. This is the best way to keep the company’s systems safe from attacks.


The Old Methodology:


In penetration testing, we come across many stories where regular testing methods didn’t catch tricky problems. These stories help us learn and get better at finding weak spots.

One common issue that often slips through is called Cross-Site Scripting, or XSS. This problem lets hackers put harmful code on websites that look safe. Even though it’s well-known, it still happens a lot because it can be hard to spot with just the usual checks.



But there’s more to watch out for than just XSS. As companies get better at fixing these known issues, hackers are getting smarter too. They’re now looking for deeper problems in how businesses run their online stuff. This includes finding ways to trick the systems into giving away secret information or letting them do things they shouldn’t. These are called business logic and information-gathering vulnerabilities.


For example, imagine a website that lets you send gifts to friends. A regular check might say it’s all good. But a smart tester, thinking like a hacker, might find a way to send unlimited gifts without paying, just by messing with the website’s rules. This kind of problem is exactly what we need to catch because it can lead to big losses for the company.


By studying these types of cases, we see that just doing the same old tests isn’t enough. We need to be creative and think about all the different ways someone might try to break in or trick the system. This helps us find the sneaky problems that the regular checks might miss, keeping everything safer in the end.

Let's understand the ToolKit:

n making our penetration testing even stronger, it’s important to think outside the usual box, especially when it comes to injection attacks. Typically, we might focus on common characters used in these attacks, like quotation marks or semicolons. However, to catch vulnerabilities that slip past standard defences, we need to broaden our toolkit.

Consider using a wider variety of inputs in your tests. This includes options like:

● Backticks, which are often used in scripting languages

● Null characters, which can sometimes terminate strings unexpectedly

● Zalgo text, which combines multiple characters into dense, complex inputs

● Multibyte characters, which represent a broader range of global language symbols than single-byte characters.


Why does this even matter?

Because systems and applications might handle these unusual inputs in unexpected ways. For example, a system might be well-protected against traditional injection techniques but may not properly process a string containing multibyte characters or Zalgo text. This oversight could open up a door for a clever attacker.

By using these inputs in our testing routines, we can uncover hidden vulnerabilities that would otherwise remain undetected. This approach pushes us to consider how an attacker might exploit overlooked aspects of input handling, ensuring our defences are as robust as possible against a wide array of attack vectors.



Analysis of Web Application Architecture

In examining web applications, it becomes clear that different segments of an application may be vulnerable to a variety of attacks. The importance of conducting comprehensive testing goes beyond just scratching the surface.



Let’s understand how various parts of a web application can present unique vulnerabilities:

1. Front-End (Client-Side) Vulnerabilities:

The front-end, which includes HTML, CSS, and JavaScript, can be exploited through attacks like Cross-Site Scripting (XSS). For example, if user input is not properly sanitized, an attacker could inject malicious scripts that run in other users’ browsers, leading to data theft or account compromise.

2. Back-End (Server-Side) Vulnerabilities:

The server side, where business logic and data access layers are there, is often targeted through SQL Injection (SQLi) or Remote Code Execution (RCE) attacks. An example case study might reveal how inadequate input validation allowed attackers to manipulate SQL queries, which leads to accessing or manipulating sensitive data stored in the database.

3.APIs and Web Services:

Many applications interact with APIs and web services for various functionalities.

These interfaces can be exploited through attacks such as Injection attacks or Insecure Direct Object References (IDOR), where attackers manipulate API requests to access unauthorized information. A case study says how poorly secured API endpoints permitted unauthorized access to user data.

4. Authentication and Session Management:

Faults in authentication mechanisms can lead to vulnerabilities like Session Hijacking or Credential Stuffing, where attackers gain unauthorized access to user accounts. The attackers bypassed weak authentication checks can highlight the need for multi-factor authentication and secure session management practices.

5. Configuration and Deployment:

Misconfiguration deployment practices can expose applications to attacks such as Security Misconfiguration or Sensitive Data Exposure. For instance, it said that default configurations and inadequate encryption practices led to data breaches.

These examples of web architecture say different vulnerabilities can exist at multiple layers of a web application’s architecture. Each layer requires a dedicated focus during penetration testing to uncover potential weaknesses.

It’s not enough to perform superficial checks, testers must employ a variety of techniques and tools to tackle each component of the application thoroughly.


Importance of Manual testing:


Manual testing is super important in checking for security issues that automatic tools might not catch. While those tools are fast and can find a lot of problems, they can’t always understand the tricky parts of an app the way a person can. A tester looking at the app by hand can spot hidden mistakes and issues, like when something in the app doesn’t work the way it’s supposed to because of a special situation.


What Does a Tester Need to Do?

Testers should dig into every part of an app, even the small details like HTTP headers or how data is sent and received. Think like someone trying to break into the app.

Don’t just stick to the usual checks. Try to find new ways things could go wrong. This means being creative and thinking about all the different ways someone might try to attack the app.

Keeping apps safe from hackers is a never-ending job because the bad guys keep finding new tricks. Automated tools are helpful, but they can’t do everything. This is why manual testing — when people check the app by hand — is so important. It helps find the sneaky problems that automated tools might miss.

Staying safe from cyber-attacks means always learning and getting better at testing. As hackers come up with new ways to cause trouble, testers need to be smart and come up with new ways to stop them.

This means always learning, being creative, and not being afraid to try new things. By working together and always looking for ways to improve, we can keep our digital world safer.



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