What is a Penetration Test?

by | Jun 7, 2022 | Penetration Testing

What is a Penetration Test?

A penetration test or “pentest” is a certified cybersecurity assessment that uses safe exploits to analyze the security of your infrastructure. The goal is to identify the systems’ strengths and weaknesses, so you can decide how to address any vulnerabilities or security threats your company faces.

A malicious actor used to require a lot of skill to gain access and move through a company’s security protections. Unfortunately, technological advancements have made it easier to find an organization’s most vulnerable points.

When done correctly, penetration testing goes beyond preventing malicious actors from gaining unauthorized access to a company’s systems. It simulates realistic scenarios demonstrating how well present defenses might perform in the face of a full-scale cyber attack.

What Are the Benefits of Performing a Penetration Test?

  • Prevent Breaches

The goal of a penetration test is to find vulnerabilities within a network, web application, and/or its associated devices and determine how they might be exploited. This allows the company to devise an action plan for remediating them. After addressing said vulnerabilities, the organization can perform a retest to verify remediation. If it is successful, the system is less likely to be compromised.

A penetration test can also reveal gaps in policies and procedures like update processes, change management, password policies, and QA procedures.

Even with a devoted internal security team, it’s easy to overlook vulnerabilities due to a lack of knowledge about malicious actors’ latest cybersecurity attack methods. If you turn to a professional penetration testing company, the consultants performing the pentest will view your environment with a fresh pair of eyes. Moreover, they’ll be well-versed in the latest threats facing your industry today because it’s their job to stay informed.

  • Ensures Compliance

Regulatory compliance standards like PCI-DSS, ISO 27001, SOC 2, and GDPR require organizations to perform audits or mandatory testing such as penetration testing. Some regulations, like HIPAA, do not directly state that penetration testing is required but do say a risk analysis must be performed. For example, performing risk analysis, 45 CFR § 164.308 (Administrative Safeguards) states:

“Conduct an accurate and thorough assessment of the potential risks and vulnerabilities to the confidentiality, integrity, and availability of electronic protected health information (ePHI) held by the covered entity or business associate.”

To find potential risks and vulnerabilities, your company should perform penetration testing. As long as you turn to a reputable and professional penetration testing company, the process will reveal security gaps and explain how they relate to the confidentiality, integrity, and availability of ePHI.

Remember: To comply with 45 CFR 164.308, all eight Administrative Safeguards criteria must be met. Even if there is no ePHI breach due to them, failing to appoint a Security Officer, performing security and awareness training, or constructing a backup strategy are all deemed HIPAA breaches.

  • Manage Risks

In today’s chaotic digital environment, every self-respecting business owner should implement a vulnerability management program based on risk-oriented prioritization. Risk management involves identifying, evaluating, and prioritizing risks so one can monitor, control, and eventually minimize the probability and negative impact of events detrimental to security as a whole.

Managing risk can be difficult if you only use automated tools like vulnerability scanners. When evaluating an entire network, a scanner alone can identify gaps within each system; however, it cannot use logic to determine the likelihood and impact of an attacker exploiting any vulnerabilities it identifies.

For example, imagine two systems with the same vulnerability for remote code execution. One system is on the external network, is domain joined, and has connections to internal systems. The other is on the internal network, is not joined to the domain, and is on an isolated test network. An automated scanner will give the same criticality to both systems, but in reality, the internal system on a lab network is less risky than the external system.

By performing penetration testing, a consultant can note each system’s vulnerabilities and prioritize which systems need to be remediated immediately based on their real-world risks.

  • Tests Security Controls

A penetration test is an effective way to test security controls by determining if they can stop attacks. It will also let you know if the controls are fine-tuned to detect malicious activities. For example, the defensive team (blue) has a chance to determine if their Security Information and Event Management (SIEM) is picking up events or can adjust their Web Application Firewall (WAF) to stop attacks against their web application.

Aside from technical controls, the organization can use a penetration test to determine if its policies and procedures are responding to threats appropriately. Moreover, a social engineering assessment can reveal how your employees report phishing emails and how your blue team reacts to such attacks.

For password management, a penetration test can reveal whether your password policy is robust enough to stop malicious actors from guessing passwords or easily cracking password hashes after obtaining them.

  • Protects Your Reputation

Suffering a breach can be disastrous as it can damage your systems and result in hefty fines. Even worse, however, is the damage it can do to your reputation. If your customers and stakeholders feel you do not take security seriously, they will do less business with your organization.

Automated Scans Versus Manual Penetration Testing

Vulnerability scans like Nexpose and Nessus check systems for known vulnerabilities and then alert the organization about possible risks. Penetration tests find flaws in your IT network’s architecture and estimate the likelihood of a malicious actor gaining unauthorized access to your critical assets. A manual penetration test can also exploit complex vulnerabilities and discover the depth of the problem, whereas a vulnerability scanner cannot.

Additionally, vulnerability scans often yield false positives. On the other hand, a penetration test should not since the tester will exploit the flaw manually to show proof of concept.

Lastly, a penetration test can find vulnerabilities using logic that automated scanners miss. For example, a vulnerability scanner will not alert against a file share that stores critical information with read/write access for the “everyone” group.

Types of Penetration Test Approaches (white-box, black-box, gray-box, and pros/cons)

You can take several approaches to penetration testing, including white-box, gray-box, and black-box. Some of the most frequently asked questions about choosing the right approach include:

  • Does the penetration testing company’s IP address need to be whitelisted when testing?
  • Should the client organization provide credentials when testing a web application?
  • Should the penetration testing company simulate an external malicious actor to test our existing security protections accurately?
  • Isn’t getting insider information about the network or application before the test a kind of cheating?

To answer such questions, consider the benefits and drawbacks of each method of penetration testing, which you will find below:

Black-Box Testing

In a black-box engagement, the tester is not given access to the web applications or networks. The tester must do reconnaissance to get the sensitive information required to proceed.

This approach is the most realistic simulation of a cyber-attack. However, it takes a long time and has the most significant risk of overlooking a vulnerability within a network or application’s internal parts. A real-life attacker usually has no time limits and can create an attack strategy over months while waiting for the ideal chance to strike.

Furthermore, various defensive technologies are available within networks to prevent existing vulnerabilities from being exploited. Several web browsers now offer options to prevent attacks even if a vulnerability still exists. However, changing the settings or connecting from a different browse is all that may be needed to exploit the said vulnerability.

The fact that security settings keep a vulnerability from being discovered or exploited does not indicate the vulnerability does not exist or is being mitigated. It simply signifies that some other variable is influencing the outcome. Someone with more time can eventually take advantage of this false sense of security.

Gray-Box Testing

Beginning with basic background knowledge and low-level credentials facilitates a more efficient and simplified process when it comes to penetration testing. This knowledge and limited access can save time during the reconnaissance phase, allowing the consultants to concentrate their efforts on exploiting possible vulnerabilities in higher-risk systems rather than trying to figure out where they could be in the first place.

Gray-box testing allows the tester to gain internal access and information from lower-level credentials, application logic flow charts, and/or network infrastructure maps. This access can represent a malicious insider or an attacker who has already breached the network’s perimeter and has restricted access.

White-Box Testing

When performing white-box testing, the penetration test consultant has complete access to all web applications and systems. The consultant also has network access with high-level capabilities and can see source code.

White-box testing tries to find flaws in logical vulnerabilities, possible security exposures, security misconfigurations, poorly written development code, and a lack of protective mechanisms, among other things. Internal and external vulnerabilities are assessed from a “behind the scenes” perspective unavailable to conventional attackers, making this evaluation complete.

White-box testing is often reserved for high-risk systems or those that process sensitive data since it takes so much time to properly analyze all parts of the system.

Summary of Each Approach

blackbox, whitebox, graybox summary

Which Approach Is Best for Your Company?

A penetration test is designed to find as many exploitable security flaws in your systems as possible before attackers do. The consultant’s degree of access and overall skill will impact how detailed and accurate the results will be.

Defining the issues you want to address is critical to creating a tailored method that meets all of the necessary security criteria while also getting the most out of your penetration test.

As every company is unique, every engagement is customized by Artifice Security’s team of highly trained OSCP, OSWE, and OSCE-certified consultants. We recognize that not every architecture or application fits into a preset box and that developing a solution that works best for your business will necessitate an adaptive testing technique.

We only use automated testing for 5% of our testing. The remaining 95% is made up of manually performed penetration testing attacks. Whether you need a black-box, gray-box, or white-box assessment, Artifice Security has the knowledge and ability to help you secure your system and avoid costly data breaches.

Types of Penetration Tests

Below are the types of penetration tests offered by Artifice Security:

Web Application Penetration Test

Web application penetration testing identifies any vulnerabilities, security issues, or dangers in a web application using manual or automated penetration tests. The penetration tester simulates attacks from an attacker’s perspective, such as SQL injection testing. The main goal of web application penetration testing is to find security flaws throughout the whole web application and its components (source code, database, back-end network). It also aids in the prioritization of discovered vulnerabilities and threats, as well as appropriate mitigation strategies.

Network Penetration Test (Internal/External)

A network penetration test will replicate real-world attacks utilizing manual penetration testing approaches beyond basic vulnerability scanning. The network pentest will reveal your organization’s network security weaknesses and how they influence your external and internal networks.

Cloud Penetration Testing

In addition to providing a configuration review, a cloud penetration test uses the most up-to-date methodologies and technologies to find and exploit vulnerabilities in cloud infrastructures such as Amazon Web Services (AWS), Microsoft Azure, and Google Cloud Platform.

Social Engineering Assessment

A social engineering assessment will examine your organization’s susceptibility to spear-phishing emails, vishing (voice calls), and on-site physical social engineering to determine where training and technical measures are lacking. A combination of human and electronic attack vectors simulates malicious actors targeting your organization.

Mobile Application Penetration Testing

A mobile application penetration test is an assessment against iOS and Android applications to identify weaknesses and ensure the mobile application security is working. To ensure the code is secure, Artifice Security will perform additional testing, such as dynamic and static assessments of the applications.

Wireless Penetration Testing

A wireless penetration test examines your wireless network, revealing flaws in your wireless configuration. Checks are run to find misconfigurations and vulnerabilities that can be exploited, and a data-driven action plan is given to fix the faults and mitigate risk.

IoT Penetration Testing

IoT testing covers a range of devices found in every industry, including mission-critical Industrial Control Systems (ICS) and supervisory control and data acquisition (SCADA) systems. This examination goes beyond basic testing to reveal vulnerabilities in interfaces and APIs, firmware, hardware, communications channels and protocols, and encryption while employing manual testing procedures to find known and unknown flaws.

Red Team Assessment

A red team assessment uses expert red teamers that simulate real-world attacks from the adversary’s perspective using an approach designed for mature security programs. The assessment tests the organization’s detection and response capabilities using real-world hostile behaviors, tactics, methods, and procedures (TTP).

Wrapping Up

Penetration testing should not be performed only once. Continuously hardening your environment to avoid breaches should be part of your defensive toolset. As a result, companies should conduct regular penetration testing to uncover and prevent exploitable vulnerabilities. Please get in touch with us using the form below or the link here to learn more about penetration testing and how it may benefit you.

Jason Zaffuto, founder, and lead Consultant at Artifice Security has over 23 years of experience in IT security and electronics. In his spare time, Jason and his wife Mia enjoy spending time outdoors visiting national parks and aviation, where Jason has his pilot license for helicopters. Jason s personal mission is to educate people and businesses about the importance of cybersecurity awareness. View Profile

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