In the AI-first future, governed by malware, deep fakes, and attacks driven by behavior analysis, cyber security will be on the frontline. With organizations transitioning from closed-loop monoliths to a collective force dependent on cloud infrastructures and third-party API vendors, the risks of the snowball effect of supply chain attacks are on the rise.
Thus, even though you might invest in securing your web application, can your API vendor? More importantly, does he choose to? Such cyber inequity necessitates traditional website penetration testing to evolve to not only secure the application but also establish safeguards for the underlying cloud infrastructure and consumed API endpoints.
What is Website Penetration Testing?
Website Penetration Testing is a simulated hacker-style attack on a website to identify and evaluate its existing vulnerabilities and protect it from malicious attacks. Typically, vulnerability assessment is the first step towards security, using automated and manual methods to uncover vulnerabilities, followed by a manual penetration test.
Web applications are often vulnerable to severe vulnerabilities like broken authentication and insecure deserialization, and the most common injection vulnerabilities can cause extensive damage. Regular website penetration testing is essential to safeguard web applications against these threats.
In fact, experts highlight that three out of four organizations are unprepared for cyber-attacks and data breaches, making penetration testing essential. Before diving in, let’s learn more about how it differs from a security audit.
Security Audit vs. Penetration Testing
Feature | Security Audit | Penetration Testing |
---|---|---|
Goal | Assess compliance with security policies and regulations | Identify and exploit vulnerabilities in systems |
Methodology | Review documentation, policies, procedures, and controls | Simulate attacker behavior to find weaknesses |
Focus | Security posture, adherence to standards | Specific vulnerabilities and their potential impact |
Outcome | Pass/fail against security controls, recommendations for improvement | Report on vulnerabilities, exploitability, and risk level |
Expertise Required | Security frameworks, regulations, and auditing standards | Network security, system administration, hacking techniques |
Cost | Typically less expensive | Can be more expensive due to specialized skills required |
Frequency | Regularly scheduled (e.g., annually) | Can be done periodically or after significant changes |
Disruption | Minimal disruption to ongoing operations | May require temporary access to systems and potential for disruption |
Compliance | Often required to meet industry regulations or contractual obligations | Not directly required for compliance, but helps demonstrate due diligence |

Why Astra is the best in pentesting?
- We’re the only company that combines automated & manual pentest to create a one-of-a-kind pentest platform.
- Vetted scans ensure zero false positives.
- Our intelligent vulnerability scanner emulates hacker behavior & evolves with every pentest.
- Astra’s scanner helps you shift left by integrating with your CI/CD.
- Our platform helps you uncover, manage & fix vulnerabilities in one place.
- Trusted by the brands you trust like Agora, Spicejet, Muthoot, Dream11, etc.

Types of Penetration Testing
Black Box Penetration Testing
This type of testing is where the tester has no prior knowledge of the web application and its configurations. It simulates a real-world attack where the attacker tries to gather information and exploit the vulnerabilities. Such a test provides a better perspective on the application’s security from an external perspective.
Black Box testers use techniques like social engineering, brute forcing credentials, or vulnerability scanners to identify and exploit vulnerabilities.
White Box Penetration Testing
In a white box test, the tester has complete knowledge and access to the application’s internal workings. It typically includes code reviews, configuration reviews, and a penetration test. Also known as a clear box test, it helps view the complete web app from an insider’s point of view.
White Box testers have complete access to the system’s architecture, codebase, and network configurations, allowing them to perform an in-depth analysis of the assets.
Grey Box Penetration Testing
Here, the tester has some knowledge of the web application and may have access to some user accounts or the application’s architecture. Used primarily to focus on testing and exploitation purposes, it is a balanced test with the depth of a white box test but real-world attack scenarios as a black box test.
Grey Box testers usually test inside out using mature automated scanners to identify known weaknesses, exploit publicly documented vulnerabilities, and perform manual testing focused on specific functionalities.
Factors | Black-Box Penetration Testing | Gray-Box Penetration Testing | White-Box Penetration Testing |
---|---|---|---|
Intel of the target system | No intel. | Partial intel. | Complete intel. |
Environment tested | Tests only the exposed environment. | Tests exposed & internal environments. | Thorough testing of all assets - external, internal, and code. |
Depth of testing | Provides a surface-level view of security posture. | Fairly in-depth. | Very in-depth. |
Guesswork | Consists of guesswork, and hit & miss sessions. | Very limited use of guesswork involved. | No guesswork involved. |
Automation | Automation is heavily used. | Automation is used sparsely. | Automation is used only as an aid to the manual process. |
Completion time | Unpredictable completion time. | Predictable. Takes several days to a couple of weeks to complete. | Predictable. Takes a couple of months to complete. |
Cost | Is usually more affordable. | Costs lie between the two extremes. | Is costly. |
Why Do You Need Website Penetration Testing?
1. Detection of Vulnerabilities
Website penetration testing can help detect and identify vulnerabilities hidden within the website, including common misconfigurations, CVEs, logic errors, or payment issues.
This helps quickly remediate critical vulnerabilities, such as broken authentication, injection attacks, or remote code execution, enhancing the overall website security.
2. Enhances Your Website Security
Beyond identifying vulnerabilities, pentesting helps enhance your web applications’ security by strengthening the measures that have already been implemented. This lets you ensure that any required improvements are made quickly and potential risks are thwarted.
3. Aids in Achieving Compliance
Regular testing allows organizations to stay on top of regulatory compliance requirements like ISO 27001, PCI-DSS, HIPAA, and GDPR, which mandate or recommend penetration testing for websites.
This helps maintain a strong security posture and avoid paying hefty non-compliance fines.

How to Perform a Website Penetration Test?
A website security penetration test is conducted using a series of methodical steps that help identify and exploit vulnerabilities in a web application. Here is a step-by-step guide for performing a professional web penetration test:
1. Reconnaissance
Information gathering is the first and one of the most important steps in reconnaissance. In this step, we gather as much information as possible about the web application, such as the various technologies used and their versions, the web server and its version, the OS being used, etc.
Key Tools Used During The Reconnaissance Phase:
- Nmap
- GoBuster
- GoBuster
- Harvester
- Astra Pentest
Type of Findings That The Reconnaissance Phase Yields:
- Open ports with services like SSH, FTP, Email Services, MySQL, etc.
- Subdomains like ‘mail.example.com’ and ‘admin.example.com’
- An API-endpoint
api.example.com/api/v2/users/33764
- URLs of S3 buckets storing images and other files

These observations now pave the way for our further testing of these potential weaknesses in the application.
Vulnerability Scanning
The next step is to use automated tools to look for vulnerabilities, such as misconfigurations, known CVEs, and weak endpoints.
Key Tools Used During The Vulnerability Scanning Phase:
- Astra Pentest
- OWASP ZAP
- Nikto
- Open VAS
Type of Findings The Vulnerability Scanning Phase Yields:
- A potential SQL Injection on a search form query.
- Session Management issue, which allows multiple sessions for user accounts.
- A Directory Traversal vulnerability that allows you to go through the folder structure and find sensitive configuration files.
3. Exploitation
This is the most critical phase of a pentest, where you actively exploit the uncovered vulnerabilities to determine the full extent of their impact.
Key Tools Used During the Vulnerability Scanning Phase:
- SQLmap
- XSSer
- CyberChef
- JohnTheRipper
- Metasploit
- BeEF
Using Findings From The Reconnaissance and Vulnerability Scanning Phase to Create an Exploit
- We use SQLmap, a comprehensive SQLi tool, to exploit the potential SQLi in the search form. It helps us extract a list of usernames and hashed passwords from the database.

- We found configuration files through the directory traversal vulnerability. We went through the files and found various API keys and that a particular user named Mike is the admin.

- Now that we know ‘daniel1984’ is an admin, we can get admin access through their account, but our password is hashed. We can try default credentials or common passwords to gain access.

- If that fails, we can try decrypting the hashed password we found during SQL injection with tools like CyberChef or JohnTheRipper. And it works!

- Now, we can use the username and password to gain admin privileges to the web application.

Similarly, we follow up on all our other observations from the first two phases and uncover more potential threats to the web application.
4. Reporting and Remediation
After successfully exploiting the vulnerabilities, the findings are compiled into detailed reports with necessary information, such as severity, CVSS score, impact, and, most importantly, the remediation to resolve this vulnerability.
Astra Pentest is built by the team of experts that helped secure Microsoft, Adobe, Facebook, and Buffer

Website Penetration Testing Checklist
Information Gathering
- Port Scanning
- Web Server, CMS Version, and OS fingerprinting.
- HTTP Methods used
- Cookie Attributes
- DNS Enumeration
Discovery
- Directory and File brute force.
- Finding default configurations or misconfigurations.
- Login Fuzzing.
- Testing Session Tokens.
- Testing File Upload Mechanism
- Business Logic Flaws.
- Denial of Service.
- Testing REST and SOAP web services.
Injections
- SQL Injection
- Cross-Site Scripting
- XML injection
- Open Redirection
- Local & Remote File Inclusion
- Host Header Injection
- HTML Injection
- Serve-Side Request Forgery
Encryption Flaws
- Heartbleed
- Poodle
- HTTPS strip
- Oracle Padding Attack
- Weak Cryptography or Poor implementation
Authentication & Authorization
- Broken Access Control
- Session Fixation
- MFA Bypass
- Privilege Escalation
Client-Side Testing
- Cross-Site Request Forgery
- Clickjacking
- Local & Session Storage Analysis
- Content Security Policy (CSP) Bypass
Final Thoughts
To conclude, website penetration testing is crucial in ensuring the security and compliance of your digital assets with industrial standards. Although a large arsenal of open-source and paid tools is available, only you can choose the ideal combination with the expertise of security engineers to safeguard your web apps.
Don’t wait for a cyberattack to expose your vulnerabilities. Get started today and test your website security with a cutting-edge tool like Astra Security. Our community of experts goes beyond the basics to offer detailed reporting capabilities with step-by-step remediation.

FAQs
How much does website penetration testing cost?
Website penetration testing costs between $349 and $1499 per scan or has different packages depending on the scope, number of assets, or number of scans required. Check out Astra’s pricing.
What is the timeline for Website Penetration Testing?
The typical timeline for website Pentesting is 7-10 days after onboarding. This timeline covers the actual testing and reporting phase. The timeline may also differ slightly depending on the scope of the test.
Why choose Astra Pentest?
1250+ tests, adherence to global security standards, an intuitive dashboard with dynamic visualization of vulnerabilities and their severity, security audit with simultaneous remediation assistance, and multiple rescans are the features that give Astra an edge over all competitors. Check Astra’s Pentest features here.
Do small websites also need VAPT?
Yes. Research shows that nearly 60% of cyberattacks target small businesses with small websites, as they don’t prioritize the security of their applications. If left insecure, smaller websites become easy targets for attackers.
Thanks for explaining the things. There are many-things which clears my doubt regarding penetration testing.
Thank you, Amit
This is really a nice and informative article.
wonderful writeup in a common man language. Thnak you for not bombing jargons!
Are website penetration testing and online pentesting the same?
Hey Aisley, website penetration testing and online penetration testing are interchangeable terms referring to the penetration testing done to find vulnerabilities within a website before any harm or breach occurs, hope this helps you.
Why should we use online pentesting platforms?
Hey Jessica, opting for online penetration testing platforms helps ensure the security of a system through the identification of vulnerabilities and their subsequent exploitation to understand the extent of possible damage. This can help in placing appropriate security patches to ensure that the system stays safe from any malicious attacks.