What is a Penetration Test?

by | Jun 7, 2022 | Penetration Testing

What is a Penetration Test, and Why Do I Need One?

A penetration test or “pentest” is a certified cybersecurity assessment that uses safe exploits to analyze the security of your infrastructure. This test identifies the strengths and weaknesses of your infrastructure, how to address vulnerabilities and the security threats that your company faces.

A malicious actor gaining access and moving through a company’s security protections used to require a lot of time and skill. However, today’s technological advances make it easier for malicious actors to find an organization’s most vulnerable points.

Penetration testing, when done correctly, goes beyond simply preventing malicious actors from gaining unauthorized access to a company’s systems. It produces realistic scenarios that demonstrate how well a company’s present defenses might perform in the face of a full-scale cyber-attack.

Benefits of a Penetration Test

  • Helps Prevent Breaches

The ultimate goal of a penetration test is to find all vulnerabilities within your network, web application, and devices while showing the organization how these vulnerabilities can be exploited. After the company remediates its vulnerabilities and performs a retest to verify remediation, the organization is less likely to be compromised by vulnerable systems. 

Additionally, a penetration test will show you gaps in your policies and procedures, such as update processes, change management, password policies, QA procedures, etc.

While many organizations have their internal security team, it is easy to be biased against your network or not see vulnerabilities due to a lack of knowledge about malicious actors’ latest cybersecurity attack methods. When choosing a professional penetration testing company, the consultants performing the pentest will view your environment with a fresh pair of eyes which typically yields excellent results.

  • Compliance

Regulatory compliance standards such as PCI-DSS, ISO 27001, SOC 2, GDPR, and others require organizations to perform audits or mandatory testing such as penetration testing. Some compliances, such as HIPAA, do not directly state that penetration testing is required, but it says that a risk analysis needs to be performed. 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 to discover vulnerabilities in your organization and how they relate to the confidentiality, integrity, and availability of ePHI.

It is critical to understand that 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, perform security and awareness training, or construct a backup strategy are all deemed HIPAA breaches.

  • Manage Risks

In today’s digital environment, it appears that every self-respecting business owner must implement a competent vulnerability management program based on risk-oriented prioritization in their entire corporate security strategy. As a procedure, risk management involves identifying, evaluating, and prioritizing risks so that one can monitor, control, and eventually minimize the probability and negative impact of events detrimental to security as a whole.

Managing risks can be difficult if you only use automated tools such as vulnerability scanners. When scanning your entire internal network, a vulnerability scanner alone will show vulnerabilities for each system. Still, it cannot use logic to determine the likelihood and impact of an attacker exploiting the vulnerability.

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 system 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, whereas in reality, the internal system on a lab network is less of a risk than the external system.

By performing penetration testing, a consultant can note all of the vulnerabilities for each system and prioritize which systems need to be remediated first by their real-world risks.

  • Test Security Controls

A penetration test is an effective way to test your security controls by determining if they can stop attacks or to ensure your security controls are fined tuned to detect malicious activities. For example, the defensive team (blue team) 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 determine if its policies and procedures are complete and working when responding to threats. For example, a social engineering assessment can reveal how your employees report phishing emails and how your blue team reacts to such an attack.

For password management, a penetration test can help determine if your password policy is robust enough to stop malicious actors from guessing passwords or easily cracking password hashes if a malicious actor obtains password hashes.

  • Reputation

Having a breach in your organization can be disastrous as it can damage your systems and cost you fines and damage your reputation. If your customers and stakeholders feel that you do not take security seriously, they will do less business with your organization. 

By performing a penetration test, your organization can show your clients that you take their security seriously as you have taken steps to find vulnerabilities and address them.

Automated scans versus manual penetration testing

Vulnerability scans, such as Nexpose and Nessus, check your systems for known vulnerabilities and alert your company 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. The penetration test will also exploit complex vulnerabilities and discover the depth of the problem while a vulnerability scanner cannot.

Additionally, vulnerability scans will have many false positives, while a penetration test should not, as the penetration tester will manually exploit the flaw and show proof of concepts.

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)

For penetration testing, there are several approaches you can choose from, such as a white-box, gray-box, and black-box approach. Most people ask, “Which approach type should I choose from?”

Several of the most often asked questions when it comes to choosing the testing 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 accurately test our existing security protections?
  • 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 of the three methods of penetration testing: black-box, grey-box, and white-box.

Black-box Testing

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

This approach is the most realistic simulation of a cyber-attack available. 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.

Furthermore, various defensive technologies are available within networks to aid in the prevention of existing vulnerabilities being exploited. Even if a vulnerability still exists, several web browsers now offer options to prevent attacks. All that may be necessary is a change in settings or a connection from a different browser version to exploit the vulnerability.

The fact 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 exploit this false sense of security to investigate this attack surface thoroughly.

Gray-box Testing

Beginning with basic background knowledge and low-level credentials facilitates a more efficient and simplified process. 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.

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

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 analyze all parts of the system properly.

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 before an attacker does. The consultant’s degree of access and skill will impact how detailed and accurate the test findings 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. So whether you need a black-box, grey-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 that 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 includes real-world adversarial behaviors and tactics, techniques, and procedures (TTP) to test your organization’s detection and response capabilities. The assessment tests the organization’s detection and response capabilities using real-world hostile behaviors, tactics, methods, and procedures (TTP).


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.

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