Penetration Testing: Process, Tools, Importance and Techniques

Penetration testing is an essential strategy used by managed service providers (MSPs) to provide their clients with greater cybersecurity.

Businesses use this technique to learn how their information security staff and procedures would behave under attack.

The primary purpose of penetration tests is to mimic an attack on a network to identify security gaps in an organization's defenses and test the readiness of its security team.  

According to some predictions, a cyberattack is projected to occur in the United States every 14 seconds, with total losses estimated to exceed $21.5 billion.

Penetration testing services can help a business prepare for hacker assaults, malware, and other threats by continuously and routinely testing for weaknesses, vulnerabilities, and inappropriate user behavior on apps, services, and networks.  

This article delves deep into penetration testing, its types, importance, advantages, techniques, and some of the standard tools included in a genuine penetration test.  

What Is Penetration Testing?

Penetration testing, also known as pen testing, is a security activity in which ethical hackers attempt to compromise an organization's systems in supervised red team/blue team drills. 

It is a method for "stress testing" the security of your IT system. It utilizes penetration techniques to examine the network's safety and security in a regulated manner. 

The objectives of a penetration test may include evaluating the procedures, preparedness, and teamwork of security personnel, cooperation between in-house and outsourced security providers, security vulnerabilities and gaps, security tools and defenses, and incident response procedures. 

Two Sides Comprise a Penetration Test:

1. It is a real test that enables a company to identify its security vulnerabilities and repair them.
2. It guarantees that security teams and tools are up-to-date and "battle-tested"; this is crucial given the rarity of large-scale security incidents and the constant evolution of attacker tools, methods, and procedures (TTPs). 

A penetration test can help a business find its vulnerabilities and assess its security processes without waiting for a genuine attack. 

However, penetration testing is not restricted to just networks; it may also be run on individual web applications and smaller equipment.  

The three most frequent kinds of penetration tests are as follows: 

1. Internal penetration testing — the attack originates within the network.
2. External penetration test — the assault commences from outside the boundary.
3. Physical penetration test — the tester achieves physical access to the organization by employing social engineering and other means. 

Why Penetration Testing?

There are several reasons why penetration tests (or "pen tests") should be performed routinely. 

Firstly, penetration testing can aid in ensuring the following: 

• security of user data, 
• identifying security flaws, 
• locating system flaws, and 
• evaluating the overall effectiveness of existing defenses.

In addition, penetration testing can help a company remain current with each new software release. 

As risks evolve, financial and PI data must be secured iteratively; as new devices are introduced to a system, moving data between different endpoints requires ongoing monitoring and compliance review.

Importance of Penetration Testing

Similarly, penetration testing provides several significant advantages.  

• It enables managed service providers to demonstrate competence and proactively handle vulnerabilities.
• It helps enterprises save money by preventing network downtime. Finally, penetration testing methods can aid MSP customers in meeting regulatory standards and avoiding fines. 
• It is essential for preserving an MSP's image, reputation, and customer loyalty.
• Penetration testing is unstructured and inventive. For instance, while one test may employ brute force, another may use spear phishing to target corporate officials. 

This ingenuity is crucial, as competent attackers will employ the same abilities and inventions to identify the organization's security vulnerabilities. 

• An additional advantage of penetration testers is that external contractors conduct them, and it is possible to select how much information about internal systems to provide.
• A penetration test can imitate either an external attacker unaware of the internal network or a privileged insider.

The best way to evaluate a company's defenses is using a "blind" penetration test, in which the security and operations teams are unaware of its existence. 

However, even if internal teams are aware of the test, it can still serve as a security drill to evaluate how tools, people, and security processes interact in a real-world scenario. 

What Are Penetration Testing Types?

According to industry experts, the three most used classifications for penetration testing are black box testing, white box testing, and grey box testing. The categories correspond to various forms of cyberattacks and cyber threats. 

The focus of black box testing is a brute-force approach. This scenario simulates the actions of a hacker unaware of the complexity and structure of an organization's IT system. 

Therefore, the hacker will undertake an all-out attack to identify and exploit a vulnerability.  

The penetration test provides the tester with no information about a web application's source code or software architecture. Instead, the tester employs a "trial and error" methodology to determine where IT infrastructure vulnerabilities exist. 

This penetration testing method resembles a real-world scenario; however, completion can be lengthy. 

White box penetration testing is the antithesis of this first method. In white box testing, the tester has complete IT infrastructure knowledge and access to the web application's source code and software architecture.  

This allows them to hone in on specific system components and conduct component-specific testing and analysis. This procedure is quicker than black box testing.  

On the other hand, white box penetration testing employs more advanced penetration testing tools, such as software code analyzers and debugging applications. 

When the tester has a limited understanding of the internal IT infrastructure, grey box testing combines manual and automated testing techniques.  

For instance, the tester may obtain the software code but not the system architecture specifications. 

Gray box penetration testing is a combination of white box and black box testing that enables the user to employ automated tools for the full-scale attack while focusing their manual work on discovering "security flaws." 

These broad categories of penetration testing methods can be further broken into granular divisions. 

Other forms of penetration tests include the following: 

Social Engineering Test

In this test, an individual is coerced into divulging sensitive information, such as passwords and business-critical data. Targeted helpdesks, workers, and processes focus on these assessments, which are conducted primarily via phone or the internet. 

Human mistake is the most common cause of security flaws. Therefore, all staff employees should adhere to security policies and regulations to prevent social engineering intrusions. Examples of these norms include the prohibition against disclosing sensitive information through email or telephone. In addition, it is possible to conduct security audits to discover and repair process issues. 

Web Application Testing

One can determine if the program is vulnerable to security flaws using software methods. It verifies the security vulnerabilities of web applications and software installed in the target environment. 

Physical Penetration Test

Strong physical security methods are used to secure sensitive data. This is typically utilized in government and military facilities. All network devices and access points are examined for potential security vulnerabilities. This test is not particularly useful for software testing. 

Network Services Test

This is one of the most typical penetration tests. The network's entry points are determined based on the systems accessed to determine the types of vulnerabilities present. This can be accomplished either locally or remotely.

Client-Side Test

Typically, a client-side penetration test can discover specific assaults. Cross-site scripting (XSS) assaults, form hijacking, HTML injections, clickjacking attacks, and malware infestations are a few examples.

It seeks out and exploits vulnerabilities in client-side software applications. 

Remote Dial-Up War Dial

It searches for modems in the environment and attempts to log in to the computers linked via these modems by guessing or brute-forcing the password. 

Wireless Security Test

It identifies open, unauthorized, and less secure hotspots or Wi-Fi networks and connects them. 

All penetration testing methods should evaluate internal and external IT infrastructure components.  

Penetration Testing Services

There are both manual and automated penetration testing services. 

Manual Penetration Testing 

Manual pen testing is exhaustive and methodical. Typically, it is performed by a contractor or security consulting firm whose testing scope is agreed upon with the client. 

Within this scope, an ethical hacker searches for vulnerabilities, attempts to compromise the organization's systems and compiles a comprehensive report describing their findings and recommending corrective action. 

Pros of Manual Penetration Testing: 

• Capability to simulate sophisticated attack campaigns involving numerous threat vectors. 
• Identifies weaknesses in business logic, as opposed to generic vulnerabilities that are simple to detect with automated methods.
• Still using automated technologies, human penetration testers can mix automatic scans with manual investigation and analysis.
• False positives are not a worry, as the penetration tester verifies all findings before generating the report.
• Capability to uncover zero-day vulnerabilities. 

Cons of Manual Penetration Testing:

• High cost and considerable effort are required for each penetration test.
• Typically, testing is only possible periodically or annually, leaving the firm vulnerable to zero-day attacks or vulnerabilities caused by changes to production systems.
• Depends heavily on the abilities of the tester. 
• Unskilled testers or those lacking knowledge of the organization's industry or technology stack are susceptible to overlooking critical vulnerabilities and insights.
• From the organization's standpoint, the setup is complex, requiring contracts, a precise scope specification, and collaboration with internal stakeholders. 

Penetration Testing as a Service (PTaaS)

The new paradigm of penetration testing as a service (PTaaS) provides enterprises with an automated platform for performing penetration testing on their systems.  

PTaaS systems utilize technologies such as automatic vulnerability scanning, dynamic application security testing (DAST), and fuzzing to identify security vulnerabilities and attempt to attack them automatically. 

Pros of Penetration Testing as a Service (PTaaS):

• The self-service paradigm allows the client to select which systems and at what intervals each test will be performed via a web interface.
• Allows firms with a minimal or nonexistent security team to conduct penetration testing.
• Most services provide a subscription or pay-per-use pricing at reduced prices and flexible payment options.
• PTaaS solutions can provide automated reporting tailored to the enterprise's needs, including compliance requirements.

Cons of Penetration Testing as a Service (PTaaS):

• Increases the organization's responsibilities, as they must define the testing schedule and independently review results.
• Some cloud providers need permission to perform automated penetration testing on their infrastructure and limit testing to a predetermined time frame.
• Encryption of under-test systems can make PTaaS services more difficult to use.
• Most services are unable to uncover business logic flaws.
• More false positives than manual testing. 

Bright is a PTaaS service that automates numerous manual penetration testing procedures. Bright offers a PTaaS platform that eliminates many drawbacks of manual PTaaS services.  

It employs artificial intelligence (AI), fuzzing techniques, and extensive threat intelligence to identify a lengthy list of known vulnerabilities in addition to zero-day attacks and business logic flaws. 

In addition, Bright leverages browser automation to deliver zero false positives; it scans many layers of your environment, including online applications and APIs, and generates findings comparable to those caused by manual penetration testers. 

Penetration Testing Process

There are six acknowledged penetration testing procedures. They include planning, reconnaissance and information collecting, scanning and discovery, attack and gaining access, maintaining access and penetration, and risk analysis and report generation. 

These steps may vary slightly from MSP to MSP based on the desired frequency and type of penetration testing. 

1. Preparing for Pen Testing

Determining the test's scope and objectives is the initial step in penetration testing. 

Next, MSPs must collaborate with their customers to determine the necessary logistics, expectations, objectives, and systems.  

Finally, during the planning phase, it will be determined whether a black-box, white-box, or grey-box penetration testing method will be utilized. 

2. Reconnaissance and Source Information

During this phase, the "hacker" or penetration tester attempts to learn as much as possible about the target. They will collect information regarding end uses, systems, and applications, among other things. 

The information will be utilized to conduct a precise penetration test, utilizing a comprehensive and exhaustive rundown of systems to determine precisely what must be handled and assessed. 

During this phase, search engine queries, domain name searches, internet footprinting, social engineering, and even the examination of tax records may be employed to gather personal information. 

3. Researching and Discovering

The purpose of the scanning and discovery phase is to determine how the target system will react to various intrusion attempts. The penetration tester often employs automated penetration testing tools to identify initial vulnerabilities. The penetration tester uses both static and dynamic analysis methods. 

Static analysis examines an application's code to forecast how it will respond to an intrusion. 

The dynamic analysis examines the code of an application while it executes, offering a picture of its performance in real time. 

In addition to network hosts, a pen tester will investigate network systems, servers, devices, and hosts. 

4. Attack and Obtain Admission

After thoroughly grasping the scope and components to be evaluated, the penetration tester will launch an attack in a simulated and controlled environment. 

The tester may take control of a device to extract data, perform a web application assault such as cross-site scripting or SQL injection, or conduct a physical attack, as described earlier.  

This phase determines how deeply a tester may penetrate an IT environment without being detected. 

To protect PI and other sensitive data, the project's scope should dictate the extent of the test's limitations.

5. Preserving Access and Penetrability

Once a penetration tester has successfully penetrated their target, they should aim to increase their access and remain for as long as possible. Again, the objective is to mimic a real-world terrible actor as closely as feasible.  

In this step, the penetration tester will attempt to expand their permissions, locate user data, and remain inconspicuous as they run their programs deeper into the IT architecture. For instance, a penetration tester may attempt to gain administrator privileges.  

Again, the objective is to remain unnoticed as long as possible and access the most sensitive data (according to the project scope and goals). 

6. Risk Evaluation and Report

The last element of a penetration test consists of an evaluation and report. A final report will be generated once the penetration tester has been "found" or the project schedule has been met.  

The report should include a summary of the testing, details of each step the pen tester took to infiltrate systems and processes, descriptions of the vulnerabilities, and recommendations for security improvements.  

A competent penetration tester will also be able to assess the worth of the compromised systems, i.e., how much their intrusion will cost financially. A penetration tester employs penetration testing tools to accomplish this. 

Carrying Out Pen Testing

Tools for penetration testing can offer the input required to complete the full assessment of cybersecurity. Using data encryption mechanisms and testing logins and passwords, pen testing tools detect security vulnerabilities.  

They resemble some tools a professional hacker might use to attempt system penetration. In addition, automated tools can benefit black box and grey box penetration tests. 

Port scanners, vulnerability scanners, and application scanners are the many categories of penetration testing tools. Remote port scanners collect information and personal data about a target. 

Scanners look for known vulnerabilities in both network hosts and networks. Finally, application scanners examine web apps for vulnerabilities.

While penetration testing is possible, it is not the most efficient method because it is time-consuming, complicated, and requires in-depth security expertise. However, if you wish to utilize a penetration tool, there are several essential aspects to consider while choosing software or a program. 

When choosing a penetration tool, ensure that it is simple to implement and customize for your specific requirements. The penetration tool should readily scan your system and be able to validate any earlier warning signs.  

In addition, the tool should be able to identify and rank vulnerabilities according to their severity, allowing you to prioritize what has to be addressed promptly. 

Finally, a component of automation should verify vulnerabilities on your behalf and generate detailed logs. 

Penetration Testing Tools

Common application vulnerabilities can be identified with the aid of automated technologies. The purpose of pentesting tools is to look for malicious code that could lead to a security breach.

By analyzing data encryption techniques and determining hard-coded information such as usernames and passwords, pentesting programs can detect security flaws within a system. 

Criteria for Choosing the Most Efficient Penetration Tool:

• It must be simple to deploy, configure, and employ.
• It should be simple to scan the system.
• It should categorize vulnerabilities under their severity and the urgency of their repair.
• It must be capable of automating the vulnerability testing process.
• It should re-verify the exploits discovered in the past.
• It should produce comprehensive vulnerability reports and logs. 

Here is a list of recommended penetration testing tools: 

Acunetix

Acunetix WVS provides security professionals and software engineers with an impressive array of functionality in a simple, straightforward, and highly robust solution. 

Intruder

Intruder is a powerful vulnerability scanner that identifies cybersecurity vulnerabilities in your digital estate, discusses the associated risks, and aids in their remedy before a breach. It is the ideal instrument for automating penetration testing operations. 

Features:

• Over 9,000 automated inspections are performed on your complete IT infrastructure.
• Infrastructure and web-layer validations, including SQL injection and cross-site scripting.
• Scan your system automatically when new threats are detected.
• Multiple connectors are available, including AWS, Azure, Google Cloud, API, Jira, and Teams.
• Intruder provides a free 30-day trial for their Pro package. 

Astra Pentest

Astra Pentest is an enterprise-wide, industry-compatible security testing tool. They have a sophisticated vulnerability scanner and a staff of skilled and highly motivated pen-testers who ensure that every vulnerability is identified and the most effective solution is provided.

Features:

• Visualized dashboard
• Continuous scanning with CI/CD integration identifies weaknesses in business logic, price manipulation, and privileged escalation.
• You may scan behind the logged-in page with Astra's login recorder addon.
• Examine advanced web applications (PWA) vs. single-page applications.
• Real-time compliance reporting.
• Zero false positives 

Penetration Testing Best Practices

The following best practices will help you increase the efficiency of penetration testing activities. 

Planning and Reconnaissance are Crucial

Vulnerability scans and a thorough search for security holes should be the first steps in a penetration test. Then, a penetration tester should conduct reconnaissance against the target company, gathering data from accessible resources, and preparing the most efficient attacks, just like a real attacker would. 

It is wise to take meticulous notes, including any vulnerabilities that were found but not used in the test. Developers may be able to replicate and solve errors in the future as a result. 

Create Attacker Avatars

An ethical hacker should behave and think like an attacker. They should think about cyber attackers' motives, objectives, and capabilities. 

Understanding hacker behavior requires an understanding of motivation. For instance, a hacker looking to steal sensitive information or a hacktivist looking to cause harm will behave differently than one looking to commit financial fraud. The organization should establish the personas of its most likely attackers, rank them, and focus on the best persona before conducting penetration tests. 

Suspend Development in the Penetration Testing Environment

A known, stable system state is necessary for effective penetration testing. The penetration test will be rendered useless by adding a new patch or software package, modifying a hardware element, or altering the configuration. This is because the update may fix any vulnerabilities that were found.

Penetration testing is done because it is not always possible to foresee whether an update will positively or negatively impact security. When systems must be changed during a test because there is no other option, the attacker should be informed, and this information should be included in the penetration test report. 

Conclusion

In conclusion, Penetration Testing is conducted while the application operates as intended. Depending on the application's requirements, a different type of testing procedure is then implemented in the application. An approved hacker identifies the application's weak points in advance, preventing any unethical hacker from gaining access.