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Penetration Testing — A Detailed Guide

Penetration Testing - A Very Comprehensive Guide
Penetration Testing - A Very Comprehensive Guide

Penetration testing is a common technique used to analyze the security posture of IT infrastructure. Web application penetration testing can assist you in identifying the potential security weaknesses in your web-based applications so that they can be fixed before attackers exploit them.

According to a recent study by Ponemon Institute and Mend, organizations are beginning to increasingly prioritize application security to guard against external attacks, data theft, and privilege abuse. Out of the surveyed respondents, 53% secure their applications using external penetration testing, while 46% use internal penetration methods. Though this shows a promising trend, more work needs to be done to address the vulnerabilities compromising information security.

This article talks about how you can use penetration testing to help you identify where you’re likely to face an attack and proactively seal those loopholes before malicious exploitations happen.

What Is Penetration Testing?

Penetration testing, also called pentesting or ethical hacking, is an authorized simulated attack used to find out the vulnerabilities that a malicious attacker could exploit in computer systems. Within the context of web application security, you can use pentesting to reveal weak opportunities in your application’s defenses that malicious players could take advantage of. 

Basically, it involves looking at your application through the eyes of bad actors and detecting security gaps before they do. At the end of the pentesting, testers usually produce a report that outlines the identified vulnerabilities, exploits, and possible fixes. The results of the ethical hacking exercise can help you to fine-tune the security of your web applications and patch the discovered flaws.

Vulnerabilities that attackers could exploit may arise from several issues, including:

  • Unknown or known software defects
  • Improper or poor application configuration
  • Weak software design framework
  • Weak threat identification mechanisms
  • Security policy errors
  • Absence of security consciousness across the team 

Pentesting requires consent between the organization and the tester; otherwise, it is malicious and illegal. If management does not approve it could unfairly expose the organization’s weaknesses and cause damage to it. 

Organizations usually hire external contractors to carry out penetration testing. Since third-party security professionals lack in-house knowledge about how the system operates, it allows them to be more exhaustive and inventive. An internal developer may not properly see some things through the eyes of the threat actor.

Some organizations also offer bug bounty programs that promise payment or prizes in case external security professionals manage to hack their systems and expose vulnerabilities.

Why Is Pentesting Important?

  • Penetration testing allows you to challenge the security of your applications and unveil critical flaws. With the current proliferation of cyberattacks, pentests can help you identify vulnerabilities that could bring your applications to their knees. The Herjavec Group estimates that cybercrime will cost the world more than $6 trillion annually by 2021. The increased reliance on online services during the Covid-19 pandemic has led to an unprecedented rise in the number of cyberattacks. Keeping your applications secure has never been more important. 
  • Penetration testing helps you to implement solid security measures. While testing the defenses of your application researchers will discover anomalies that could compromise your security. This helps you proactively bridge those gaps and ward off possible attacks. It’s the best way of providing context and validating the implementation of new security measures.
  • Penetration testing enables you to comply with various security regulatory standards, such as GDPR, HIPAA, and PCI DSS. With the current emphasis on data security, organizations are expected to keep their users’ data safe and secure. Pentests allow you to adhere to the compliance standards by empowering you to seal the loopholes that attackers can use to exfiltrate users’ sensitive data. Compliance also helps in assuring your customers and other stakeholders that their data is properly safeguarded.

The Difference Between Pentesting And Vulnerability Assessment

Penetration testing and vulnerability assessment are not the same thing — though each of them aims to detect vulnerabilities and reinforce the security of your IT infrastructure.

Vulnerability assessment, also known as vulnerability scanning, refers to conducting tests that discover known weaknesses, or vulnerabilities, in your system. An automated vulnerability scanner is usually used to identify threats as well as assess the quantifiable value and significance of each vulnerability, allowing you to prioritize remediation effectively. 

On the other hand, penetration testing deliberately simulates a cyberattack and exploits the identified vulnerabilities. It’s a different way of rooting out weaknesses in your applications. While vulnerability scanning is critical to your organization’s application security posture, pentesting helps cover other methods intruders can use to exploit a security flaw.

Vulnerability scanning is an important stage in penetration testing. When conducting pentests, vulnerability scans help in detecting the weaknesses that exist in the target system.

Penetration Testing Stages

Pentesting is a comprehensive exercise that comprises several steps. These are the main stages of penetration testing:

  1. Penetration test scope definition
  2. Reconnaissance of target systems
  3. Vulnerability assessment
  4. Penetration testing
  5. Lateral movement
  6. Risk analysis and recommendations
  7. Penetration test report

Major Approaches To Pentesting

Pentests differ based on the target system, conditions of the test, and the objectives to be achieved. The organization usually provides the security testers with varying levels of information about the vulnerable system.

These are the main approaches to penetration testing:

  1. Black box testing
  2. White box testing
  3. Gray box testing

Penetration Testing Tools

There are a wide variety of tools that security professionals can use to carry out pentesting. Broadly, the tools can be categorized into the following groups:

  • Port scanners—these are reconnaissance tools used for probing network hosts and open ports, and collecting information about them.
  • Vulnerability scanners—these are used for discovering the known vulnerabilities in your system. They typically detect the CVEs (Common Vulnerabilities and Exposures) and compare them against those reported in repositories like the NVD (National Vulnerability Database). 
  • Application scanners—these assess the flaws in web applications that malicious actors could exploit. 
  • Web application proxy tools—these are man-in-the-middle proxies or other specialized web proxies that can eavesdrop on the traffic between the pentester’s browser and the target web server. 


Web application pentesting helps to detect vulnerabilities and address them before attackers compromise your systems. Pentesting is essential to taking your application’s security to the next level. 

If you do not do penetration testing on a regular basis, your applications could be susceptible to attacks. As new cyber threats emerge, malicious intruders could use them to wreak havoc on your system. 

Pentests help ensure you’re a step ahead of the attackers. That’s the best way to keep your systems secure in this age of rising cyberattacks. 

Meet The Author

Adam Murray

Adam Murray is a content writer at Mend. He began his career in corporate communications and PR, in London and New York, before moving to Tel Aviv. He’s spent the last ten years working with tech companies like Amdocs, Gilat Satellite Systems, Allot Communications, and Sisense. He holds a Ph.D. in English Literature. When he’s not spending time with his wife and son, he’s preoccupied with his beloved football team, Tottenham Hotspur.

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