Penetration Testing (pen Testing)


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A penetration test, commonly known as the pen test or the ethical hack, is an authorization simulation cyber attack conducted against a computer to assess the security of a system. This test is done by testing the vulnerability (also known as vulnerability) to evaluate weaknesses in computer systems. The process usually identifies a target system and a specific objective, examines available information, and tests various methods to meet these goals.


Penetration testing concepts can be traced back to some of the earliest reports on computer security. For example, in 1969, the United States Department of Defense observed that "hostile attempts to degrade system operations" and "network reconnaissance activities" are among the most severe violations of computer security.

In 1971, Willis Ware wrote a paper for RAND Corporation detailing three categories of "computer security violation":

In 1989, the first US Computer Crime laws were passed to deal with computer crime. In 1991, a presidential directive stated that these tests are an official measure for evaluating government department system safety. In 1997, The EC Council issued the first version of its Penetration Testing Execution Standard (PTES), which is now on its seventh iteration.

In 2000, the US National Security Agency (NSA) collaborated with the EC Council to publish a document containing computer vulnerability exploitation guidelines and penetrations issued by the Russian KGB. These documents remain available on the NSA website and provide an excellent insight into penetration test methodologies and procedures used by these highly skilled professionals.

The UK Royal Air Force conducts security research testing for new IT systems under development called "Project Emphasis," which is still referenced in their official policies today. It has become clear that penetration tests are valuable automated testing tools in evaluating risks associated with networked computing devices, applications, or websites operated by organizations of any size. Information security can be enhanced through well-designed penetration tests as technology evolves at breakneck speeds worldwide.

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Penetration test steps

The following steps are commonly followed to complete a penetration test:


2-Target identification and analysis

3-Vulnerability Analysis




7-Technical controls implementation (if required)

8- Nontechnical controls implementation(if required)

Laptop requirements

When conducting a penetration test, you will be required to perform actions and activities that violate the law. To comply with legal requirements and minimize your company's liability, we recommend using a dedicated PC (laptop) during your testing. A dedicated laptop/computer for testing helps to eliminate any potential risks of information leakage or data loss. It also allows testers not to worry about accidentally deleting critical files or breaking existing systems they are targeting during the test.

Pen testing methods

There are several methods used in penetration tests, including:

-Active surveillance is the primary method used by hackers before attacking a target network for identifying security weaknesses on all possible entry points of the company's infrastructure

-ive reconnaissance is more passive than an active survey, yet it is still an essential aspect of any penetration test. Passive surveillance involves identifying the visible presence of the target on the Internet, mapping its network boundaries, and determining its possible vulnerabilities without making direct contact with any company systems.

-Scanning involves probing every device connected to a public Internet Protocol (IP) network for network ports that are open or vulnerable due to misconfiguration, software malfunction, or out-of-date software versions. This step can help determine what operating systems and applications run on those devices and other visible information about each publicly accessible system's security posture.

-Vulnerability analysis includes confirming discovered vulnerabilities as well as investigating if other potential risks may exist in the targeted environment

-Exploitation involves taking control of a vulnerable computer system or computing device by performing actions that could lead to creating, modifying, or deleting data files/directories, executing programs, changing settings/configurations, accessing private information, and impersonating users.

-Enumeration is another popular method used in penetration testing. It helps identify additional details about the mapped network infrastructure, including the Internet presence of systems and user accounts on those devices. Enumeration can be an essential step towards escalating privileges, including obtaining valid login credentials.

-Privilege escalation allows attackers to access unauthorized functions or content that would otherwise be inaccessible if the hacker had started at the lowest security level. Privilege escalation is often easier than most people think, which has led many investigators worldwide to share their stories of privilege escalation and other penetration testing techniques.

-Backdoors are tools often installed by hackers to gain future access to a compromised system. Hackers can use backdoors to bypass authentication screens, download additional software tools, upload stolen data, and many other actions that may go undetected for months or years without any proper security controls in place.

-Denial-of-service (DoS) attacks block the availability of targeted computing devices and services on the Internet, including web servers, network routing equipment, domain name system (DNS), email servers, and many others. DoS attacks don't require complex double-blind testing techniques since they only aim at exhausting target resources such as bandwidth or memory before legitimate users can access those online assets.

Note that this list is not exhaustive since new penetration testing techniques are regularly created or discovered worldwide.

Penetration testing target

As mentioned earlier, penetration tests can be designed to focus on almost any aspect of a company's security posture ranging from physical access control systems used by employees and visitors to decrypting wireless network traffic being sent over the airwaves. The following sections detail several of these testing concepts for readers who are just beginning their journey of learning more about penetration testing. In addition, penetration tests may aim to assess the entire information technology infrastructure, including all major business applications running on internal servers and web applications accessed by users located both inside and outside the organization's perimeter.

-Applications are often one of the most vulnerable parts of any company's security environment since they are regularly developed by third-party vendors or outsourced to inexperienced developers with limited budgets.

Inside or outside

Many of the most successful penetration tests begin by identifying all entry points into a target environment, including physical, wireless, and virtual connection methods used by computers. The following list includes common types of network connections that may be considered for various forms of penetration testing: Physical: employees who bring personal mobile devices into work pose one of the most significant risks to every organization's security posture. If an IT department does not adequately monitor those tools, then malicious activity originating from those devices may go undetected until some significant incident occurs. This is often more problematic when connecting mobile devices to VPNs or authenticating users with one-time passwords.

Wireless: most companies that rely on Wi-Fi for network access leave themselves open to the possibility of an attack since there are many common types of wireless network attacks, including Evil Twin, Jamming, Deauthentication, and others. Hackers can use these approaches to capture sensitive information being transferred between company systems over insecure or unencrypted protocols such as HTTP(S)

Virtual private networks (VPNs): employees whose computers are configured with VPN access may also introduce malicious activity into a corporate environment without IT departments realizing it. One way to prevent this security breach is by routinely monitoring VPN traffic with secure web proxies.

What's in your mind

Penetration testing is sometimes also used to assess an organization's resiliency in the face of a significant incident such as a hurricane, fire, or earthquake. In these situations, hackers may take advantage of a company's reduced ability to monitor and control security events within its infrastructure by launching attacks designed to steal data, alter business records, or bring down online services.

-Social engineering: social engineering is one of the oldest forms of information gathering activities in any IT environment since it often requires little technical knowledge about how computer networks operate. However, this form of attack can be highly effective at compromising sensitive corporate information, especially when employees are tricked into believing that requests for sensitive internal data originate from someone inside their organization

-Operating system weaknesses: operating system vulnerabilities pose another risk factor that penetration testing can help to identify since there are dozens of known operating system exploits that may be used by hackers to remotely control systems and initiate various types of attacks against other company computers

-Web application weaknesses: web applications provide a wealth of information about their organization's infrastructure, including databases, servers, and other services. Hackers who specialize in attacking sensitive web-based products such as customer relationship management (CRM) suites or content management systems (CMSs) can use this data for various malicious purposes. This includes downloading sensitive information from the target network, creating new user accounts on trusted systems, controlling financial processes attributed to business partners within an organization

To achieve maximum flexibility when performing a penetration test, several penetration testing providers offer various services that enable an organization's IT staff to select the correct assessment approach for their specific needs. This may include combining the white box, gray box, and black box penetration testing methods.

The following sections will review different types of penetration testing commonly used by organizations when performing security assessments against internal business systems.

What you will learn

-White box penetration testing

-Black box penetration testing

-Gray box penetration testing

Advantages of Penetration Testing

What are the key advantages of conducting a penetration test? Organizations implement security systems to keep out unauthorized guests but often fail to consider that a practical attack method may already exist due to one or more entry points in their physical infrastructure. Penetration testing provides an organization's IT staff with another way of identifying these vulnerabilities to take corrective measures before any damage is done to company operations. This ensures better protection for sensitive data assets while improving team member productivity by reducing downtime caused by malicious activities within the environment.

However skilled company employees may be, they cannot provide all the necessary aspects to protect sensitive data assets. For this reason, penetration testing has become a staple security assessment method used by organizations around the world to provide legitimacy and validation of their security strategies. In addition, well-executed penetration tests enable businesses to take proactive measures against attackers who may already be lurking within their internal networks.

What are Black Box, White Box, and Gray Box Penetration Testing

Penetration testing, also known as pen testing tools or ethical hacking, is essentially an evaluation activity aimed at evaluating the effectiveness of existing security systems and detecting potential vulnerabilities within them before hackers do. A penetration test can be conducted by applying several different methodologies and techniques, including white-box penetration testing (also known as a transparent box), black-box penetration testing (also known as an opaque box), and gray-box penetration testing.

Since an organization's IT security infrastructure is likely to be a crucial asset, the objective of all forms of penetration testing is to identify vulnerabilities that could put a company at a higher risk for data compromise. This may include discovering ways in which attackers can gain access to company systems and networks through various entry points such as server ports, user accounts, operating system configurations, weak encryption standards, network protocols used for communication between services and devices within the environment etc.

White box penetration testing offers a complete insight into an organization's security infrastructure, including its servers and network devices. In this type of assessment methodology, both systems and applications are comprehensively tested by experts. The tests display all components that need to be secured against potential attacks, including network equipment, servers, operating systems, services, protocols, user accounts, etc. Employees usually carry out White-box penetration testing with detailed knowledge of its IT infrastructure.

White box penetration testing should be used when assessing complex environments that are difficult to investigate due to high complexities or large numbers of users and assets or when evaluating third-party service providers where there is no privilege given to the security testers for information gathering purposes.

Black Box Penetration Testing

Thorough security assessments against an organization's IT security infrastructure require black box penetration testing. In this type of assessment methodology, expert evaluators are provided with no additional knowledge about the organization's internal environment, such as network components and applications within the IT infrastructure. This lack of privileged information is beneficial as it allows security testers to evaluate the environment on the same level as potential attackers who are not privy to company secrets. Both external and internal security professionals can perform black-box penetration testing

Black box penetration testing provides organizations with an unbiased view of their security posture. There are, however, significant drawbacks associated with this approach. For instance, it may be difficult for experts to gain access to specific components within an organization's IT infrastructure without knowing its layout due to a lack of intelligence about the environment. This assessment methodology is also less effective against complex environments where different networks exist behind a common entry point or systems use non-standard ports that could complicate connection attempts by security testers.

Gray Box Penetration Testing

Gray box penetration testing combines the strengths of both black-box and white-box security assessments. In this methodology, experts are granted limited knowledge about a company's IT infrastructure, which allows evaluating components that need to be tested with greater ease without compromising the organization's confidentiality. The scope of information provided to gray-box penetration testers may include network topology diagrams, asset inventories, and other details that allow for the practical testing of systems within an organization.

How Does Pen Testing Work

Penetration testing requires an in-depth, onsite analysis of its IT infrastructure. White-box and black-box penetration tests usually take between one to two weeks, while gray-box evaluations can be carried out within three to four days. During the assessment process, security experts employ various techniques designed to expose security vulnerabilities, including:

• Network mapping - this method is used to gather information about network devices and servers along with their location and configuration;

• System scanning - involves identifying all systems present within a company's IT environment and assessing them for weaknesses; • Vulnerability scanning - often employed against web applications, this type of evaluation entails running automated tools that search for software bugs such as SQL injection or cross-site scripting; and

• Password cracking - utilized to assess the strength of passwords used to protect information assets.

The outcome of penetration testing is documented in a report that outlines all security vulnerabilities found within an organization's systems and provides recommendations for resolving them. A well-written penetration test report should detail potential impacts should each issue be exploited, describe severity scores, and explain discovered problems. Furthermore, the results should provide clear instructions on eliminating the root causes of detected weaknesses.

Phases of penetration testing

Penetration Testing Phases:

Phase 1 -Reconnaissance: Information gathering, network scanning, and bare enumeration.

Phase 2 – Gaining Access: This phase exploits identified vulnerabilities and gains access to systems and sensitive information. It may also include privilege escalation and creating backdoors for future use.

Phase 3 – Maintaining Access: The main objective in this phase is to ensure the accessed environment remains compromised even after standard security controls are implemented. For example, an attacker would want any changes made to be undone, so they continue being able to access the system freely without raising suspicion or alerting administrators.

Phase 4 – covering Tracks: This refers to removing the evidence of unauthorized access from a company's environment before the penetration test ends.

GIAC penetration tester

The Penetration Testing with Kali course is aimed at IT professionals, penetration testers, and security consultants. The training will give the students in-depth knowledge of conducting professional penetration tests using the best open-source tools available.

The final goal of this training is to provide students with hands-on experience to start working as penetration testers immediately after the completion of the course.

People who are expected to get the maximum benefit from this training are:

• Security analysts or managers who have a fundamental understanding of information systems, security controls, vulnerability scanning methods, operating system commands, and general networking concepts but lack practical penetration testing experience.

• Network administrators who have some exposure to network security controls need to understand how malicious attackers exploit vulnerabilities and how to protect against such threats.

• Security consultants who would like to expand their penetration testing skills beyond the scope of using tools need a deeper understanding of the vulnerabilities, methodologies, and thought process behind a professional penetration test.

What is Penetration Testing

Penetration testing (PT) or ethical hacking attempts white-hat hackers to find security weaknesses before malicious attackers can discover and exploit them. Companies hire pen testers through consulting firms or use internal staff for this task. Pen tests simulate real-life attacks on networks and systems, so any weaknesses discovered during the exercise can be remediated before criminals get a chance to compromise them.

Companies use different types of pen tests: black box, gray box, and white box. Black-box testing involves only the tester having access to the public information about the system. Gray-box testing provides some limited knowledge of the internal workings of a system, such as IP range or server names. Finally, white box testing allows full access to an organization's systems and data.

How to pen test is helpful

Here are four key reasons why penetration testing is essential:

• It helps companies identify security holes before attackers do – Penetration tests can be run continuously to ensure that any newly identified or updated vulnerabilities are immediately addressed and corrected by IT and security teams.

• It acts as a deterrent – Many companies opt for penetration tests rather than cyber insurance because they believe it gives them a better chance of identifying vulnerabilities before they are exploited.

• It helps build stronger teams – Penetration testing can help strengthen an organization's security team by identifying weaknesses in how the team works together to address vulnerabilities. This enables them to work more efficiently and effectively after the complete test.

• It helps prioritize remediation efforts – Companies with cyber insurance policies often require penetration testing or some other form of validation that their IT environment has been tested for security risks before they provide coverage against a loss. Pen tests also enable companies to identify which vulnerabilities need immediate attention so risk ratings can be assigned appropriately and remediation prioritized accordingly.

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