Website Penetration Testing – A Complete Guide

Technical Reviewers
Updated: November 1st, 2024
8 mins read
Website Penetration Testing

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

FeatureSecurity AuditPenetration Testing
GoalAssess compliance with security policies and regulationsIdentify and exploit vulnerabilities in systems
MethodologyReview documentation, policies, procedures, and controlsSimulate attacker behavior to find weaknesses
FocusSecurity posture, adherence to standardsSpecific vulnerabilities and their potential impact
OutcomePass/fail against security controls, recommendations for improvementReport on vulnerabilities, exploitability, and risk level
Expertise RequiredSecurity frameworks, regulations, and auditing standardsNetwork security, system administration, hacking techniques
CostTypically less expensiveCan be more expensive due to specialized skills required
FrequencyRegularly scheduled (e.g., annually)Can be done periodically or after significant changes
DisruptionMinimal disruption to ongoing operationsMay require temporary access to systems and potential for disruption
ComplianceOften required to meet industry regulations or contractual obligationsNot directly required for compliance, but helps demonstrate due diligence
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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.
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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.

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.

FactorsBlack-Box Penetration TestingGray-Box Penetration TestingWhite-Box Penetration Testing
Intel of the target systemNo intel.Partial intel.Complete intel.
Environment testedTests only the exposed environment.
Tests exposed & internal environments.Thorough testing of all assets - external, internal, and code.
Depth of testingProvides a surface-level view of security posture.Fairly in-depth.
Very in-depth.
GuessworkConsists of guesswork, and hit & miss sessions.Very limited use of guesswork involved.
No guesswork involved.
AutomationAutomation is heavily used.Automation is used sparsely.
Automation is used only as an aid to the manual process.
Completion timeUnpredictable completion time.Predictable. Takes several days to a couple of weeks to complete.Predictable. Takes a couple of months to complete.
CostIs 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.

Website Penetration Testing by Astra
Image: Vulnerability Assessment & Website Penetration Testing by Astra

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
Type of Findings That The Reconnaissance Phase Yields - Astra

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.
Website Penetration Testing Exploitaion 1
  • 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.
Website Penetration Testing Exploitaion 2
  • 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.
Website Penetration Testing Exploitaion 3
  • If that fails, we can try decrypting the hashed password we found during SQL injection with tools like CyberChef or JohnTheRipper. And it works!
Website Penetration Testing Exploitaion 4
  • Now, we can use the username and password to gain admin privileges to the web application.
Website Penetration Testing Exploitaion 5

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


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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.

Website Penetration Testing Infographic

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.