Web Penetration Testing

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Web Penetration Testing
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Penetration testing aka Pen Test is the most commonly used security testing technique for web applications.
Web Application Penetration Testing is done by simulating unauthorized attacks internally or externally to gain access to sensitive data.
Web penetration helps end-users find out the possibility for a hacker to access data from the internet, find out the security of their email servers and also get to know how secure the web hosting site and server are.
Well, let’s now cover the content of this article.
In this penetration testing tutorial I have tried to cover:
Recommended Vulnerability Scanning Tools:
Netsparker is easy to use automated web application security testing platform that you can use to identify real & exploitable vulnerabilities in your websites.
Astra’s Pentest Suite combines a powerful automated vulnerability scanner and manual pen testing capabilities to create a comprehensive security testing solution for web applications with features like CI/CD integration, continuous scanning, and zero false positives.
When we talk about security, the most common word we hear is vulnerability .
When I initially started working as a security tester, I used to get confused very often with the word Vulnerability, and I am sure many of you, my readers, would fall in the same boat.
For the benefit of all my readers, I will first clarify the difference between vulnerability and pen-testing.
So, what is Vulnerability ? Vulnerability is a terminology used to identify flaws in the system which can expose the system to security threats.
Vulnerability Scanning lets the user find out the known weaknesses in the application and defines methods to fix and improve the overall security of the application. It basically finds out if security patches are installed, whether the systems are properly configured to make attacks difficult.
Pen Tests mainly simulate real-time systems and help the user find out if the system can be accessed by unauthorized users, if yes then what damage can be caused and to which data etc.
Hence, Vulnerability Scanning is a detective control method that suggests ways to improve security programs and ensure known weaknesses do not resurface, whereas a pen test is a preventive control method that gives an overall view of the system’s existing security layer.
Though both methods have their importance, it will depend on what really is expected as part of the testing.
As testers, it is imperative to be clear on the purpose of the testing before we jump into testing. If you are clear on the objective, you can very well define if you need to do a vulnerability scan or pen-testing.
Importance and the need for Web App Pen Testing: 
If you look at the current market demand, there has been a sharp increase in mobile usage, which is becoming a major potential for attacks. Accessing websites through mobile phones is prone to more frequent attacks and hence compromising data.
Penetration Testing thus becomes very important in ensuring we build a secure system that can be used by users without any worries of hacking or data loss.
The methodology is nothing but a set of security industry guidelines on how the testing should be conducted. There are some well-established and famous methodologies and standards that can be used for testing, but since each web application demands different types of tests to be performed, testers can create their own methodologies by referring to the standards available in the market.
Some of the Security Testing Methodologies and standards are –
Listed below are some of the test scenarios which can be tested as part of Web Application Penetration Testing (WAPT):
Even though I have mentioned the list, testers should not blindly create their test methodology based on the above conventional standards.
Here’s an example to prove why I am saying so.
Consider you are asked to penetration test an eCommerce website, now give it a thought if all vulnerabilities of an eCommerce website can be identified using the conventional methods of OWASP like XSS, SQL injection, etc.
The answer is a no because eCommerce works on a very different platform and technology when compared to other Websites. In order to make your pen testing for an eCommerce website effective, testers should design a methodology involving flaws like Order Management, Coupon and Reward Management, Payment Gateway Integration, and Content Management System Integration.
So, before you decide on the methodology, be very sure about what types of websites are expected to be tested and which methods will help in finding the maximum vulnerabilities.
Web applications can be penetration tested in 2 ways. Tests can be designed to simulate an inside or an outside attack.
As the name suggests, internal pen testing is done within the organization over LAN, hence it includes testing web applications hosted on the intranet.
This helps in finding out if there could be vulnerabilities that exist within the corporate firewall.
We always believe attacks can happen only externally and many a time’s internal Pentest is overlooked or not given much importance.
Basically, it includes Malicious Employee Attacks by disgruntled employees or contractors who would have resigned but are aware of internal security policies and passwords, Social Engineering Attacks, Simulation of Phishing Attacks, and Attacks using User Privileges or misuse of an unlocked terminal.
Testing is mainly done by accessing the environment without proper credentials and identifying if an
These are attacks done externally from outside the organization and include testing web applications hosted on the internet.
Testers behave like hackers who aren’t much aware of the internal system.
To simulate such attacks, testers are given the IP of the target system and do not provide any other information. They are required to search and scan public web pages and find our information about target hosts and then compromise the found hosts.
Basically, it includes testing servers, firewalls, and IDS.
Before testing starts, it is advisable to plan what types of testing will be performed, how the testing will be performed, determine if QA needs any additional access to tools, etc.
Web Penetration testing can be done from any location, given the fact that there shouldn’t be restrictions on ports and services by the internet provider.
Once the testing is complete and the test reports are shared with all concerned teams, the following list should be worked upon by all –
Since you have already read the full article, I believe you now have a much better idea of what and how we can penetration test a web application.
So tell me, can we manually perform Penetration testing or does it always happen by automating using a tool? No doubt, I think the majority of you are saying Automation. :)
That’s true because automation brings in speed, avoids manual human error, excellent coverage, and several other benefits, but as far as the Pen Test is concerned, it does require us to perform some manual testing.
Manual Testing helps in finding vulnerabilities related to Business Logic and reducing false positives.
Tools are prone to give a lot of false positives and hence manual intervention is required to determine if they are real vulnerabilities.
Tools are created to automate our testing efforts. Please find below a list of some of the tools that can be used for Pentest:
Service Providers are companies providing services catering to the testing needs of the organizations. They usually excel and hold expertise in different areas of testing, and can perform testing in their hosted test environment.
Mentioned below are some of the leading companies that provide penetration testing services:
If you are interested in getting certified in web app penetration certification, you can opt for the below certifications:
In this tutorial, we presented an overview of how penetration testing is performed for web applications.
With this information, the penetration tester can start vulnerability tests.
Ideally, penetration testing can help us create secure software. It is a costly method so the frequency can be kept as once a year.
To learn more about Penetration Testing, please read the related articles below:
Please share your views or experience on the Pentest below.
thanks for sharing. can you share one best tool for pen testing?
Not sure who ever thought a PC a.k.a “windows” box could be used as a testing device, but it is for absolute certainty when I say, “don’t make that mistake”. A PC is not a testing device. It is a target device. Testers are Linux, *Nix, MacOs += VM / Docker.
nice intro. please share examples also
Good explanation. Please share some example with every phase of it.
great article , can you please provide us with examples
I found this to be an excellent article. You mentioned Web Application Penetration Testing is done by simulating unauthorized attacks internally or externally to get access to sensitive data. In addition to internal and external testing, there is of course, double-blind testing, which can find issues that internal and external testing may not find.
Good overview about PenTesting. I just have one question. I am from InfoSec, and would like to understand how I decide PenTest is required for a an existing Web Application which recently done a small change (like modified a business logic of existing code. This code is to provide static file download.
Hi Karthik, I think the best way to decide is to first get a penetration testing done for the complete application fix all the vulneabilities and perform a pentest as a part of the relesae cycle or perform it when there’s addition of a new module added to your application. You can also perform a pentest every quarter to get better understanding of your code and security posture of your application.
Nice piece. It help us greatly. More indepth research is required in future.
Hello, I’m a novice with 0 basics and want to learn web penetration. Can a master teach me?
Good explanation for beginners, I’m sure this information will help people who are wishing to get started in the web application penetration testing space
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Image: Vulnerability Assessment & Website Penetration Testing by Astra

Get your web app audited with Astra’s Continuous Pentest Solution

With our detailed and specially curated SaaS security checklist.
Ananda Krishna is the co-founder & CTO of Astra Security, a SaaS suite that secures businesses from cyber threats. He has been acknowledged by the Indian Navy, Microsoft, United Airlines, etc. for finding critical security vulnerabilities in their systems. Winner of the Best Security Product at Global Conference on Cyberspace 2017 (awarded by Narendra Modi, Prime Minister of India) & French Tech Ticket, Paris (awarded by François Hollande, former President of France).
At Astra he's building an intelligent security ecosystem - web application firewall (WAF), malware detection & analysis, large scale SaaS applications, APIs & more. He's actively involved in the cybersecurity community and shared his knowledge at various forums & invited talks.
Website Penetration Testing is a hacker-style simulated attack to test the security posture of an organization. Learn more regarding online pen testing.
Businesses have learned the hard way that vulnerabilities & security loopholes can cost them money and more. Statistics show that as many as 99.7% of businesses have at least one undiscovered vulnerability. These security issues are nothing but a ticking bomb waiting to blow up. Ignorance is not bliss when it comes to cybersecurity. You have to identify and patch these security loopholes at the earliest to protect your website. Hence we talk about Web penetration testing in this article. 
Some common vulnerabilities such as SQL injection, Cross-site scripting (XSS), and Cross-site Request Forgery (CSRF) can easily be exploited by cybercriminals, through which they can steal sensitive data present on your website or even get complete control over your website. To avoid this, it is always good to take preventative measures such as having web pentest done for your website in order to identify and fix vulnerabilities before malicious actors take advantage of it.
So, let’s talk more about Website Penetration Testing sometimes referred to as a website security audit.
Penetration Testing is a simulated hacker-style attack on an application aimed at gauging the gravity of the existing vulnerabilities. This is to say, Penetration Testing focuses more on how each of these vulnerabilities could be exploited as opposed to Vulnerability Assessment , which merely identifies and lists all existing vulnerabilities in your website.
For example, consider a thief trying to enter your house to rob you and you want to take security measures so that the thief won’t be able to enter your house. Here, vulnerability assessment is similar to making sure you have all your house windows and doors closed. And penetration testing is similar to checking the strength or any weaknesses of your windows or doors. So that even if a thief tries to enter they will not find any entry points to enter your house and you can have a peaceful sleep.
Basically, vulnerability assessment is an initial step in the whole process. Whereas, Online Website Security Testing or pentesting uses the findings (the list of vulnerabilities) and exploits them to work out the degree of risk attached to it. Vulnerability assessment can use both automated & manual scans. Whereas, penetration testing is generally a manual process done by experienced security engineers.
While both Vulnerability Assessment & Penetration Testing concerns the same area, they are not quite the same . And have been wrongly used interchangeably in the past. This confusion has led to web owners asking for Vulnerability Assessment when they really need Penetration Testing and vice versa.
Now, I am sure, you can spot the differences between the above two.
Further in this article we will go deeper into penetration testing and take a closer look at the complete methodology involved in VAPT (tools + checklist) .
It is crucial to identify your site’s security loopholes so that you are never caught off guard. VAPT lets you anticipate possible mishaps that could take place. This invariably contributes to better risk management for your website.
I have seen website owners often ask things like, “ Mine is just a small website, do I need a Vulnerability Assessment & Penetration Testing? “.
The answer is yes. Research has it that nearly 60% of cyberattacks target small businesses. So, there’s a good chance of your website being targeted, if left untended.
In a nutshell, online penetration testing can help you in the following ways:
Web services pentest is done primarily in 3 phases:
The first phase is information gathering in which, the pentester tries to find fingerprint the backend services of the website i.e. Server OS, CMS version, etc.
Nmap has been the absolute favorite recon tool of website pentester for a long time and there is a solid reason for that. The abilities of Nmap are:
To see more options, fire your Kali in the command line terminal and type ‘nmap‘. Also, users can try Zenmap which is the GUI version of Nmap.
While tools like NMAP does a black box information gathering, there are certain tools like The Harvester which collect Open Source Intelligence (OSINT). OSINT is the information present in the public domain regarding your target i.e. Whois registration info, company emails, etc. This info comes in handy while online penetration testing. It is spread out on sites like Google, Whois, etc. So, the harvester compiles it from all sources and gives you a one-stop solution.
The second step is Discovery in which automatic tools are deployed to uncover any known flaws or known CVEs in the respective services.
Nikto is a tool specifically designed to scan vulnerabilities in around 270 types of servers. It can extensively search for 6700 server misconfiguration.
However, the limitation of Nikto is that it is very noisy and can often generate false positives. Moreover, firewall evasion techniques of Nikto are very poor. However, when combined with another Inundator (to evade IDS) of Kali, it can be effective.
Therefore, before using Nikto for website penetration testing, make sure to turn off your firewall or IDS for better results.
To scan a target using Nikto, simply open the terminal in Kali and type: nikto -h 'your-target‘
Burp Suite is a website pentesting framework built on java. It has a built-in proxy that intercepts traffic between your browser and the website pentesting target. This proxy can be then used to manipulate requests or for fuzzing to discover vulnerabilities in a website.
While manipulation of requests can help in finding vulnerabilities, fuzzing can uncover error messages and application behavior too. This tool has become almost an industry standard and is a must-have for website penetration testing.
OpenVAS is a vulnerability scanner that can perform a complete vulnerability scan of the network infrastructure. It can be easily scaled as per your needs and can perform a wide variety of tests. This tool is owned by Greenbone and the paid solution is called Greenbone Security feed while the free one is called Greenbone Community feed. The prime difference between both the editions is the NVTs (Network Vulnerability Scanner test).
Metasploit framework is almost an industry standard when it comes to the exploitation of the target. Metasploit can also perform recon using Nmap. If you find any vulnerabilities, there are a plethora of exploits to choose from. Finally, pair your exploit with a suitable payload and you are good to go. Metasploit even has a great choice of post-exploitation tools. Metasploit is owned by Rapid 7 and is written in ruby. Almost all proof of concepts of popular zero-day flaws are updated as Metasploit modules.
To launch Metasploit, open the terminal in your Kali Linux and type: ‘msfconsole‘
Sqlmap is a one-stop solution to find any SQL injection vulnerabilities on your website and exploit them. Sqlmap can fuzz the target parameters in the URL and even data fields on the page to find any SQL injection points. Sqlmap can thereafter exploit them to provide you a pseudo SQL shell or cmd shell from the target machine.
To see more options, open t
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