Penetration Testing Process and Guide

Penetration testing is a popular and successful method for identifying security flaws in an organization’s IT infrastructure. It involves performing a vulnerability assessment of your IT infrastructure by “ethically hacking” any system, network or application to simulate how a genuine hacker would operate.

Downloads:

• Penetration Testing Execution Standard (PTES) 2022 Guide – PTES is a penetration testing technique created by a group of information security practitioners to meet the need for a comprehensive and up-to-date standard in penetration testing.

The goal of a penetration test from an organizational standpoint is to evaluate existing policy controls to uncover vulnerabilities that pose a threat. The purpose of a penetration tester is to acquire access to systems and applications which will result in the exposure of sensitive information. Compliance frequently requires penetration testing of the entire organizational environment or a subset of assets supporting a regulated function. Even in the absence of regulatory obligations, it is best practice to conduct security evaluations of an organization’s assets regularly.

Real attackers have no boundaries and can attack an organization using various methods, including directly attacking internet-facing systems and apps or targeting individuals. As such, a secondary purpose is to find vulnerabilities that attackers can exploit using methods outside of the scope or rules of engagement for a specific test.

Regardless of the kind, all penetration tests often follow the same stages.

Reconnaissance

The organization’s disclosure of the target’s details is studied. This usually involves a lot of OSINT (Open Source Intelligence) to help the tester as they move through the other phases. This also helps identify goals for the tester if none are provided as part of the initial scoping efforts with the customer. This phase’s artifacts may include but are not limited to hostnames, IP addresses, employee names, and email addresses.

Enumeration of attack surfaces

The elements with which an attacker can interact are listed during this assessment step. The targeted items in the case of social engineering can be a service, a web application or even people and structures. Each parameter or interface that can be interacted with is identified.

Vulnerability detection

A vulnerability is a weakness in an organization’s system that an attacker can exploit to launch a successful attack, such as system access, information leakage, or denial of service. During this phase, vulnerabilities are found that an attacker could exploit.

Exploitation

The penetration tester exploits previously identified vulnerabilities. The collected data and access are used to gain further access to more sensitive data.

Reporting

During the evaluation, relevant artifacts are collected for reporting. After active testing, the report is sent to the client, describing the evaluation and recommending corrective measures to management and leadership teams.

Remediation and retesting

The tested organization deals with the test results. The standard way to deal with detections is to remediate disclosed vulnerabilities within the organization’s existing policies and practices. In some instances, an identified vulnerability cannot be immediately addressed but can be addressed through alternative means, such as additional security measures or compensating controls. For auditors supporting compliance initiatives, the company may occasionally need written documentation. The penetration tester might be called back in to offer proof of remediation or to evaluate the mitigation procedures. These phases are not always treated sequentially, and a penetration tester may need to revert to prior stages if necessary.

Rhyno Cybersecurity provides clients with a variety of penetration testing services. The three major categories are network penetration testing, application penetration testing, and social engineering.

Network Penetration Testing

Wireless network penetration testing

A penetration tester evaluates the wireless network defined by a customer. The tester will search for known flaws in WiFi encryption and attempt to break keys, lure users into submitting passwords to evil twin access points or captive folders, and brute force login information. A rogue access point sweep of a physical location and an authenticated wireless segmentation test can be used in conjunction with these assessment types to establish access to the network if they successfully connect to the environment.

External network penetration testing

During an external network penetration test, internet-facing assets are targeted. The client typically provides the target assets. However, “no-scope” testing can be undertaken with the client to corroborate the targets obtained by open-source intelligence (OSINT) activities. In-scope assets are scanned for vulnerabilities, which are then analyzed using commercial-grade vulnerability scanners. The tester will then attempt to exploit any vulnerabilities detected during the scan. Furthermore, any exposed services that allow for a login will be targeted using password-guessing attacks such as brute force or a password spray based on usernames gathered through OSINT activities. Exposed websites are often subjected to further examination in search of common online vulnerabilities that an unauthenticated attacker may exploit.

Internal network penetration testing is conducted from the perspective of an attacker who has acquired access to the organization’s internal network. Although the penetration tester can visit the site, internal testing in the post-COVID-19 environment is often conducted remotely. On-site testing can benefit from interaction between the tester and the customer team, while remote testing has the economic advantage of avoiding high travel expenses. The tester can negotiate remote access by utilizing either the client’s infrastructure or the tester’s physical or virtual remote testing systems.

Application penetration testing

Online and web application penetration testing

Most businesses utilize complex web applications, which attackers may exploit using various well-documented methods. Therefore, an online application’s attack surface is the main subject of a web application penetration test. These tests are designed to evaluate the web application the ordinary user uses and look for new ways to access sensitive data or take control of the web application’s operating system. During this examination, the business will often grant the tester credential access to study the whole program, as an attacker with such access may do maliciously.

Mobile application penetration testing includes static analysis of the built mobile applications as well as dynamic analysis of the program’s runtime while it is running on the device. In addition, all communications in which the device participates are reviewed and evaluated. HTTP connections containing HTML data or API requests were often used.

Thick application penetration testing

Complex reverse engineering is required for compiled apps that function on desktop or server operating systems like Windows and Linux. This form of evaluation would entail disassembling and decompiling the application, as well as attaching debuggers for runtime analysis of the program when it is running. In addition, fuzzing (injecting faulty data repeatedly) of the application’s user input parameters is conducted when possible to find faults that can lead to significant vulnerabilities. Finally, the application communications are reviewed to identify if sensitive information is being communicated insecurely or if there are chances of attacking servers supporting the application.

Social manipulation

Email social engineering (phishing)

Attackers are phishing every company. This type of assessment determines the sensitivity of the organization’s user base to spear phishing attacks. Rhyno Cybersecurity Consulting tailors the attack to be highly specific to your organization, often posing as a support agent and directing customers to login portals using your organization’s logos and language or using other sophisticated attacks discovered during the evaluation collaboration. These assessments are not intended to evaluate the performance of the organization’s email defences but rather to determine how users will behave when messages bypass such filters. The results of these assessments are used to improve the organization’s anti-social engineering awareness campaigns.

Phone social engineering (vishing)

Rhyno Cybersecurity Consultants mimic users, support employees, or customers using caller ID spoofing technologies. This assessment seeks to persuade users to take action that will provide information or grant access to an organizational system. Because of the originating phone number, many users will believe the caller. Other users will notice the attack and respond in various ways, such as confronting the consultant or alerting the information security staff following the conversation. As the scope and rules of interaction are established, contingencies for anticipated user responses are established.

Physical, social engineering

An attacker may try to infiltrate a facility to acquire access to sensitive information or attach an implanted device to give remote access for subsequent actions. Tailgating and mimicking are two methods for getting entry to the building. During a physical, social engineering engagement, Rhyno Cybersecurity Consultants will masquerade as a staff member or vendor and attempt to acquire access to the organization’s facilities. The consultants will employ props and costumes to gain the users’ trust.

Dropped USB sticks

Users may inadvertently attempt to connect USB devices to the environment. Rhyno Cybersecurity Consultants will deploy what looks to be an ordinary USB thumb drive to lure the user into inserting the device into a business system. When connected, the USB device can be a standard disk carrying malicious files that initiate remote connections or a complete keyboard that performs keystrokes. Rhyno Cybersecurity Consulting will measure the devices attached and provide the customer with the engagement findings.

SMS social engineering (smishing)

Similar to phishing, this assessment involves sending enticing messages to consumers via a short message service, often called SMS or phone text messages. These activities, like phishing, will aim to get consumers to visit sites mimicking the company or sending a dangerous payload.

What penetration testing does not include:

Many people have misconceptions regarding the nature of penetration testing. Examples of such considerations are the perceptions of parallels with real-world attackers, mimicking heavy network demands, and how the testing team will interact with the organization.

Clients will frequently seek to construct rules of engagement to make the remainder more realistic to an attacker’s behaviour. Penetration testers, on the other hand, have a limited amount of time to complete a significant amount of work. In contrast, an attacker can work stealthily in a hostile environment for months to avoid discovery. Penetration testers do not have the same amount of time as attackers. Our Red Team Exercise package is Rhyno Cybersecurity Consulting’s assessment that matches this. This assessment includes many tests to mimic an attacker’s behaviour as closely as possible.

Penetration testers make every effort to avoid disrupting production during their testing. Typically, a tester will not engage in denial of service during an evaluation. In rare cases, a denial of service attack against a specific system with a resource consumption vulnerability can be carried out.

DDoS attacks are difficult to mimic and frequently impact other firms that rely on upstream bandwidth shared by the client. Hence they are rarely used.

The penetration tester will deliver brief updates on their activity during a test. Nonetheless, due to time limits, the tester is unable to go into depth regarding particular attacks carried out at specific times. Instead, a purposeful effort between the defenders (blue team) and attackers (red team) is combined to form a purple team evaluation if the organization wants to validate detection and countermeasures are successful against specified attack types. This evaluation is considerably more measured, takes longer to complete, and gives more profound insights into the effectiveness of various countermeasures and controls in real time.

Conclusion

An organization’s offensive security assessment options provide an interesting and vital method for analyzing the security posture. Gaps in the organization’s controls, detection mechanisms, and countermeasures can be detected. The underlying causes of these difficulties should be addressed through various methods, including specific technical adjustments, rules, procedures, and processes. Most major businesses will need substantial time to make these repairs, and budget increases are usually required to successfully remedy detected weaknesses over time.

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