Penetration Testing: The Ultimate Guide

Both these processes are complementary in nature and are usually performed together, in a combined process called VAPT, or Security Audit.

Pen Testing Types

1. Cloud Pen Testing

With a growing number of companies moving towards a cloud infrastructure that makes interconnectedness more convenient than ever before, cloud pen testing is a must to keep your cloud-stored data safe.

Cloud penetration tests analyze the cloud computing environment for vulnerabilities that hackers could exploit. Based on the service model, cloud pentesting can be divided into three categories: Infrastructure as a Service (IaaS), Platform as a Service (PaaS), and Software as a Service (SaaS).

1. IaaS cloud pentesting evaluates cloud infrastructure assets, storage, and networks.
2. PaaS pentesting assesses runtime environments, development tools, and databases.
3. SaaS pentesting checks how the application stores data transmits information, and checks how it authorizes users.

Some common cloud vulnerabilities found during pentesting include insecure APIs, insecure codes, weak credentials, and server misconfigurations.

2. Network Pen Testing

A network penetration test aims to find vulnerabilities in the network infrastructure, either on-premise or in cloud environments such as Azure and AWS penetration testing.

This test tests and checks a wide range of areas, such as configurations, encryption, and outdated security patches. The tests under network pentests can be divided into internal, external, and wireless network pen testing.

1. Internal network pentesting tests the organization’s internal infrastructure to ensure the security of the network’s servers, workstations, and devices.
   
2. External network pentesting tests whether an external attacker can breach the network by conducting firewall attack vector tests and router pentests.
   
3. Wireless network pentests assess the security of all wireless devices and channels like Wi-Fi and Bluetooth to ensure no attacker can access or alter information.

Some other network pentests conducted include DNS footprinting, SSH attacks, and evasion of IPS/IDS.

3. Web Application Pen Testing

With the rise in web-based applications, vast amounts of data are stored and transmitted through them, making them attractive targets for cyber attackers.

Web app pen testing simulates attacks to find vulnerabilities in a web application to assess its internal and external security.

This is conducted in three different ways varying on the availability of information: black-box, white-box, and gray-box testing. This will be covered in detail in the section on the different approaches to pentesting.

Some of the common vulnerabilities found in web app pentests include:

• Wireless encryption and network traffic
• Unprotected access points and hotspots
• Spoofing MAC address
• DDoS Attacks
• SQL/Code Injections Attacks
• Cross-Site Scripting

4. API Pen Testing

An Application Programming Interface (API) is a set of standards that lets applications communicate with each other. It enables developers to create customized experiences within an application.

API penetration testing helps find vulnerabilities that could result in attackers getting unauthorized access to data or functions.

Some of the significant security issues tested for during an API pen test are:

• Broken authentication flaws in identification measures. 
• Broken authorization due to exposed endpoints. 
• Exposure of data.
• Misconfigurations. 
• Injection flaws such as SQL, command injections, and more. 

5. Mobile Pen Testing

Everyone uses mobile applications daily, and risks like data loss and finances come with this. Companies must stay vigilant in protecting app and customer data to avoid cyberattacks.

Expert penetration testers test mobile applications to find security vulnerabilities which can then be reported to the developers. Mobile pen testing applies to Android, iOS, Native, and Hybrid applications.

Some of the significant security issues found in mobile apps include:

• Lack of transport layer protection
• Insecure Communication
• Insecure Authentication
• Weak Encryption
• Lack of Binary protection.

6. Social Engineering Pen Testing

In contrast to testing for technological flaws, social engineering pen testing concentrates on testing and exploiting human deficiencies. It evaluates an organization’s vulnerability to social engineering techniques by simulating attacks to test the people within the organization.

Using these techniques, penetration testers can evaluate an organization’s ability to fend off social engineering assaults and pinpoint areas where security awareness policies and training need strengthening.

Standard social engineering techniques include:

• Phishing
• Pretexting
• Tailgating
• Impersonation

Who Performs Pen Testing?

Cybersecurity experts with an extensive understanding of exploitation strategies and security flaws conduct pen testing. These professionals, called pen testers, use a systematic approach to simulate real-world hacker behavior to find vulnerabilities that can be exploited.

Although some companies employ in-house security teams to conduct this testing, many hire external VAPT (vulnerability assessment and pen testing) companies. These security service providers have a wider range of expertise, an objective viewpoint, and access to cutting-edge technologies and procedures.

Steps Involved in the Pen Testing Process

Pen testing process involves several elements, including pre-engagement analysis, information gathering, vulnerability assessment, exploitation, post-exploitation, reporting, resolution and rescanning.

Here are the eight key steps involved in the pen testing process flow:

Step 1: Pre-Engagement Analysis

Before planning a test, you and your security provider must discuss the scope, budget, objectives, etc. Without these, the direction of the test will not be clear enough, resulting in a lot of wasted effort.

Step 2: Information Gathering

Before commencing the pen test, the tester will attempt to find all publicly available information about the system and anything that would help break in. This would assist in creating a plan of action and reveal potential targets.

Step 3: Vulnerability Assessment

In this stage, your application is tested for security vulnerabilities by analyzing your security infrastructure and configuration. The tester searches for any opening or security gaps that can be exploited to break into the system.

Step 4: Exploitation

Once the tester is armed with knowledge of vulnerabilities present in the system, they will start exploiting them. This will help identify the nature of the security gaps and the effort required to exploit them.

Step 5: Post-exploitation

The main objective of a pen test is to simulate a real-world attack without causing any real damage. Thus, once the tester can enter the system, they will use all available means to escalate their privileges.

Step 6: Reporting

Everything done during pen testing is documented in detail, along with steps and suggestions for fixing the discovered security flaws. Testers often have meetings and debriefs with executives and technical teams to help them understand the report.

Step 7: Resolution

Once the target organization obtains the detailed report upon completing the scan of its assets and security, it is used to rectify and remedy the vulnerabilities. This helps avoid any breaches and threats to security.

Step 8: Rescanning

Upon completing the vulnerability patching based on the pen testing report provided, a rescan is conducted to scan the new patches to test their air tightness. The application is rescanned to find any additional or new vulnerabilities that could have arisen from the patching.

Once this final step is completed and no vulnerabilities have been detected, the organization or asset is said to be secure. It is provided with a pen test certificate that is publicly verifiable and adds visible authenticity.

What are the different approaches to Pen Testing?

There are three main types of pen testing methods adopted by testers; the key differences in these approaches are based on the information available and the types of weaknesses to be identified:

1. White Box Pen Testing

In a white box pen test, the testers have complete knowledge of the system and complete access to information about it. In this case, the advantage is that since the tester has unbridled access and knowledge of the system, including code base code quality, API documentation, and internal designs, the pentest can identify even remotely located vulnerabilities, thus giving a nearly complete picture of the security.

2. Gray Box Pen Testing

As the name suggests, this approach stands midway between white-box pen testing and black-box testing. The tester has only limited knowledge of the system. The advantage of this approach is that with limited knowledge, the tester has a more focused area of attack and thus avoids any trial-and-error method of attack.

3. Black Box Pen Testing

The tester here does not know the system and designs the test as an uninformed attacker. Black box pen testing by a third party requires the pen tester to think outside the box and employ methods that a true hacker would use to break into a system. This would allow the detection, exposure, and exploitation of vulnerabilities to their fullest extent.