What is Penetration Testing?

In the current landscape, cyber threats are not only becoming more frequent but also more sophisticated. Still, the most common way hackers enter your internal network is through exploiting security vulnerabilities that already exist within your IT infrastructure. 

That’s when they wreak havoc, taking full control over your IT infrastructure.

Penetration testing or pen testing helps organizations pinpoint areas they are most likely to face a breach and proactively mitigate the vulnerabilities before malicious hackers exploit them.

What is penetration testing?

A penetration test, also known as ethical hacking, is a simulated cyberattack where ethical hackers mimic the strategies and actions of a malicious agent to identify, test, and highlight existing vulnerabilities within your organization’s systems and implement effective security controls.

When used with other technical tests, penetration testing techniques also help test the robustness of your cybersecurity policies, employees‘ security awareness, regulatory compliance, and your organization’s ability to identify and respond to security issues and incidents as they occur.

Typically, organizations should conduct a penetration test annually.

Why is penetration testing important?

A penetration test, also known as pen test, strives to evaluate your organization’s current security posture to determine how easy, or difficult, it is to access or exploit computer systems, networks, web applications, and critical data assets.

For example, a bank may hire an external consultant to break into its building and access the vault to measure their security gaps. If the burglar succeeds, the bank will know how its current security is lacking and what needs to be done to tighten its security measures. In the same way, as your business scales, you need to determine where your current critical cybersecurity gaps are within your IT environment.

In the end, you should be in a better position to handle any malicious threat actor attempting to exploit your cybersecurity gaps, significantly minimizing the impact and cost of the breach.

What is the difference between manual and automated penetration testing?

Manual pen testing and automated penetration testing serve the same purpose: to identify and eliminate possible entry points into your organization’s infrastructure. The sole difference between them is how you perform the testing—IT professionals conduct manual penetration testing, whereas automated penetration testing is done by computerized tools.

What are the benefits of a penetration test?

A carefully executed penetration test gives you visibility into real-world cyber threats to your organization. It helps you find gaps in your cybersecurity program by exploiting vulnerabilities and providing steps for cyber incident remediation.

Here are the five benefits of penetration testing:

1. Complete IT infrastructure analysis

Pen testing analyzes your IT infrastructure and its ability to defend your networks, apps, systems, and users from external and internal attempts to gain unauthorized access to protected assets or cause disturbance and data loss.

Some advantages of analyzing security infrastructure are:

• Uncovering exploitable vulnerabilities in your systems and weaknesses in your target environments: After a pen test, you’ll get a report detailing the problematic access points and vulnerabilities in your system and networks, as well as software and hardware improvement suggestions to upgrade your cybersecurity posture.
• Using novel hacking methods to identify areas of improvement: Ethical hackers simulate real cyberattacks against your systems using black hat methods, which helps them identify parts of your network and systems that need improvement.
• Reducing incident response time: When you know your systems’ vulnerabilities, you can better prepare to prevent and mitigate real cyber threats using relevant tactics and tools.
• Facilitating better IT budgeting: A pen test helps you understand your overall security posture’s weaknesses and outlines ways to amplify, modify, and optimize it. You can also identify areas that would benefit from additional spending, as well as areas where you’re losing money.

2. Encourages a more proactive approach to cybersecurity

Today, organizations have a portfolio of defensive cybersecurity technologies and tools, including SIEM solutions, IAM programs, firewalls, vulnerability scanning programs, and more. However, these tools aren’t enough to find and eliminate every vulnerability existing in your IT environment.

Penetration testing helps you become more proactive in your real-world approach to cybersecurity defenses. It helps you uncover holes in your security, prioritize cyber risks, properly remediate shortcomings, and implement additional layers (if needed) before an actual cyberattack occurs.

3. Easy (and effective) risk identification to mature security environment

A pen test identifies which channels in your organization (network, systems, apps) are most at risk—and what types of new cybersecurity tools you should invest in or protocols you should follow to mitigate risks.

Your continuous efforts to identify and eliminate risks mature your organization’s security posture, giving it a competitive advantage. It shows your customers information security and compliance are paramount for your organization, and proves your dedication to striving toward optimum cybersecurity.

4. Compliance with regulation and security certification

Pen testing helps address the compliance and security obligations mandated by industry standards and regulations, such as PCI DSS, HIPAA, ISO 27001, FISMA, and GLDA. Performing these tests regularly demonstrates due diligence and dedication to informing and improving your organization’s cybersecurity. In turn, this will help you avoid substantial penalties and fines for non-compliance.

5. Protection from financial damage and loss of business operability

A data breach will undoubtedly hurt your brand reputation, impact customer loyalty, incur unanticipated financial/legal penalties and fines, and generate negative press that could lead to millions of dollars in damages.

Frequent penetration testing avoids these expenses by controlling and preventing IT infrastructure invasions. It’s better to take proactive measures and maintain your organization’s security, rather than risk operational downtime and face the consequences of a successful cyberattack.

What are the 5 stages of penetration testing?

The pen testing process can be broken down into the following five stages:

Stage 1: Planning and reconnaissance

The first step is to define the scope and goals of the pen test, the penetration testers plan and identify the systems they’ll address and the pen testing methods they'll use. Follow this up by gathering intelligence (e.g., network and domain names) to understand how a target works and what are its potential vulnerabilities.

Stage 2: Scanning

Scanning helps you understand how the target app will respond to various intrusion attempts. You can choose between two options:

• Static analysis involves inspecting an app’s code to gauge its behavior while running. Note that these tools scan the entirety of the code at a go.
• Dynamic analysis involves inspecting an app in a running state. It's the more practical scanning method because it presents a real-time view of an app’s performance.

Stage 3: Gaining access to your IT environment and internal assets

This involves using web application attacks (e.g., cross-site scripting, backdoors, SQL injections) to uncover vulnerabilities. Next, the penetration testers exploit these managed vulnerabilities and risks by escalating privileges, stealing data, and other undesirable activities to understand the total extent of the damage malicious hackers can cause by gaining unauthorized access.

Stage 4: Maintaining access

In this stage, the penetration testers check whether the vulnerability can be used to establish a long-term presence in the compromised system, ideally long enough for the threat actor to steal your organization‘s sensitive data.

Stage 5: Analysis report

After the penetration testing is done, the results are compiled into a report outlining:

• All of the specific vulnerabilities that were exploited,
• Any sensitive data that was accessed, and
• The total time the penetration testers were able to remain in the system undetected.

Once this is complete, your security team will get a detailed list of recommendations (e.g., configure your enterprise’s WAF settings and other application security solutions to patch vulnerabilities) that you can implement protective measures against future cyberattacks.

What are the different types of penetration testing?

Before choosing a suitable cybersecurity firm for a pen test, you should be familiar with the different types of pen tests available. Here are the six main types of penetration testing:

External network penetration testing

External network penetration testing targets company assets visible on the internet to gain access and extract valuable data.

Ethical hackers try to leverage vulnerabilities found while screening your company’s publicly available information or attempt to gain access to data through external-facing assets like cloud-based apps and websites.

Internal network penetration testing

Here, penetration testers assume the role of a malicious “insider“ with a certain level of legitimate access to the internal network to identify vulnerabilities. This doesn’t necessarily involve simulating an ill-intended employee; scenarios can also include employees whose credentials have been stolen during a phishing attack.

Pen testers gauge the impact of confidential information being unwillingly disclosed, misused, altered, or destroyed. They then use the insights to recommend better controls over employees, such as enhancements to system privileges of access, vulnerable applications, and little or no segmentation.

Physical penetration testing

This type of pen testing simulates a physical breach of your security controls by an intruder to provide proof of real-life vulnerabilities. Pentesters may pose as delivery personnel to attempt to gain access into your building or as a burglar to break into your office.

Physical penetration testing also looks beyond physical testing and considers crafty threat actors like individuals plugging a malware-injecting device (for example, USB) into an employee’s computer to gain unauthorized access to your network.

Social engineering penetration testing

Social engineering penetration testing gauges how susceptible your staff is to exposing confidential information and whether they need more in-depth employee cybersecurity training and management.

Pentesters attempt to gain your employees' trust, usually by tricking them into sharing their credentials or performing an action that exposes data to a masked malicious actor. A common example is phishing emails.

Wireless penetration testing

The most common issue with wireless internet connections is anyone within the given vicinity can “eavesdrop“ on the wireless traffic flowing across your organization—all they need to do is exploit a vulnerability in your network.

By performing a wireless pen test, you’ll know whether your organization’s Wi-Fi and wireless devices/protocols are properly safeguarded.

Application penetration testing

Application pen testing identifies and focuses on vulnerabilities within your applications, from the design and development to implementation and deployment. Pentesters look for flaws in the app’s security protocol (think: missing patches, exploited holes in web applications), apps running on internal networks, and apps running on end-user devices and systems.

As hacking techniques and application updates are evolving every day, ensure to frequently test your apps for new vulnerabilities. Simply scanning isn’t enough as it only focuses on the “low hanging fruit“ problems in software code.

Common penetration testing methodologies

The following are the five standardized penetration testing methods:

• Open-Source Security Testing Methodology Manual (OSSTMM): This is a widely used penetration testing standard based on a specific approach to network pentesting. It provides testers with adaptable guides to conduct an accurate cybersecurity assessment.
• Open Web Application Security Project (OWASP): This pentesting methodology helps testers recognize vulnerabilities within the web and mobile applications and uncover security flaws within development practices. It also enables testers to rate risks, allowing them to prioritize issues to save time.
• National Institute of Standards and Technology (NIST): This penetration testing methodology gives testers precise technical testing guidelines to improve the accuracy of the pen test. High-danger industries like banking, energy, and communications can use this framework to improve overall cybersecurity.
• Penetration Testing Execution Standards (PTES): This methodology is developed by a team of information security professionals to create a comprehensive and up-to-date guide to penetration testing and create awareness among businesses as to what to expect from a pen test and what the organizational processes they should know to run successful tests.
• Information System Security Assessment Framework (ISSAF): This standard provides a specialized and structured approach to pentesting and is ideal for testers looking to plan and document every step in detail. It's also suitable for those who use different penetration testing tools, letting them tie each step to a specific tool.

What is the difference between penetration testing and vulnerability scanning?

Penetration testing and vulnerability scanning are both vital components of network security and critical to prevent cyberattacks. But they aren’t the same and follow very different methodologies to test your systems for vulnerabilities.

Vulnerability scanning involves using automated tools (i.e., vulnerability scanners) to examine an environment and finally create a report of the vulnerabilities uncovered. It assesses computer systems and network infrastructure for security weaknesses to provide a quick, high-level look at what can possibly be exploited.

Think of it this way: vulnerability testing scans digital assets to highlight pre-existing flaws, and penetration testing determines security gaps through hands-on research and exploitation of vulnerabilities.

Does your organization need penetration testing?

Assess your cyber threat prevention, threat detection, and response capabilities with eSentire.

Given how cybercriminals are evolving their operations and strategies, and how accessible it is for new threat actors to target companies using the ransomware-as-a-service model, your cybersecurity team must test your defenses to ensure you can thwart a cyberattack when the time comes.

We treat every simulated cyber threat exercise as a challenge to test the effectiveness of your cybersecurity defenses using the latest techniques designed to evade cybersecurity controls.

Learn how eSentire’s Technical Cybersecurity Testing Services can help your organization test your cybersecurity defences, contact a cybersecurity specialist today.