Understanding the Penetration Testing Lifecycle: Penetration Testing Phases & Tools

Penetration Testing
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Penetration Testing Methodologies and Tools: As organizations become more reliant on technology, such as the cloud, IoT, social media, and mobile devices, their cyber risk rises rapidly.

Hackers continuously refine their ways and regularly steal millions of documents and dollars. Penetration testing is one method of countering these threats.

In this article, we look at Penetration Testing methodologies and provide insight into some of the popular Penetration Testing tools

What is a Pen Test?

Penetration testing, commonly known as pen testing, aims to discover security flaws by conducting controlled attacks on the system or network using malicious techniques. In this method, authorized simulated attacks are used to exploit a system’s weak areas.

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A pen test is conducted by a penetration tester, also known as an ethical hacker, who aims to identify vulnerabilities that potential attackers may exploit while simulating an assault on an organization’s IT assets.

Vulnerabilities can occur for a variety of causes, the most common of which are:

  • Flaws in hardware & software design
  • Use of an unprotected network
  • Poorly designed computer systems, networks, and applications
  • Complex computer system architecture
  • Conceivable human errors

An effective penetration test reveals weaknesses in the system security that a business is utilizing, as well as different attack paths and configuration issues. As a result, a business can prioritize the risk, address it, and enhance overall security reaction time.

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Why is Penetration Testing vital?

Penetration testing is vital because it is one of the most effective ways to detect and repair security flaws in a system before an attacker can exploit them.

Organizations can avoid or limit the harm an attacker may wreak if they successfully exploit a security vulnerability by conducting penetration testing. To defend your business, you should do penetration testing regularly to:

  • Identify security weaknesses so that you may fix them or install suitable controls
  • Ensure the effectiveness of your existing security measures;
  • Identify new problems in existing software;
  • Check for vulnerabilities in new software and systems.
  • Ensure your business is complying with the GDPR and DPA 2018, as well as other relevant privacy and security laws and regulations;
  • Comply with industry standards such as the PCI DSS
  • Assure stakeholders that their data is secure

Types of Penetration Testing

There are many sorts of penetration tests based on various characteristics. Most pen tests can be segmented into three areas:

  • Penetration tests based on Target Knowledge
  • Penetrations Tests based on the Tester’s Position
  • Penetration Tests based on the Target System

Knowledge of the Target:

  • Black Box: A black-box penetration test is one in which the tester has no prior knowledge or information about the target. This type of test is time-intensive, and consequently, the penetration tester typically utilizes automated techniques to identify vulnerabilities.
  • White Box: White box penetration testing is when the tester has full knowledge of the target. This includes all IP addresses, code samples, controls, details of the operating systems used, etc. As such, this type of test needs significantly less time than black box penetration testing.
  • Grey Box: Gray-box penetration testing occurs when the tester has limited data about the system being targeted. In this scenario, the tester will have little or partial knowledge of the target information, such as IP addresses, URLs, etc., but will not have full access or knowledge.

Position of Tester:

  • External Penetration Test: These are conducted externally to the network
  • internal Penetration Test: This simulates if an attacker has breached the perimeter and is present on the corporate network
  • Targeted Test: Are performed by an organization’s IT team in collaboration with the Penetration Testing team
  • Blind Penetration Test: The tester has no prior information other than the target organization’s name
  • Double-Blind Test: Knowledge of the pen test is not disclosed to the wider business, with only one or two individuals in the business aware that a test is being performed

Target System:

Network Penetration Testing

Network penetration testing aims to identify vulnerabilities inside an organization’s network architecture. It includes firewall configuration and bypass testing, DNS assaults, Stateful analysis testing, etc. The most prevalent software packages analyzed in this test include:

  • File Transfer Protocol
  • MySQL
  • SSH, or Secure Shell
  • SMTP, or Simple Mail Transfer Protocol
  • SQL Server

Application Penetration Testing

In Application Penetration Testing, testers examine web-based apps for security vulnerabilities and weaknesses. APIs, ActiveX, Silverlight, and Java Applets are also explored as fundamental program components. Consequently, this type of testing consumes a great deal of time.

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Wireless Penetration Testing

Wireless Penetration Testing involves examining all wireless devices utilized by a company. It includes devices like tablets, laptops, and cell phones. This test aims to identify weaknesses in wireless access points (WAPs), wireless protocols, and administrative credentials.

RELATED: 10 tips for better wireless network security

Social Engineering

Social Engineering Test entails attempting to get secret or sensitive information by deceiving an organization’s employees. There are two subsets present.

  • Remote testing: This aims to manipulate an employee into revealing confidential data via an electronically
  • Physical testing: Aims to use physical means to gather sensitive data, such as threats or blackmailing an employee

RELATED: 5 Social engineering techniques that exploit business employees

Client Side Penetration Testing

The objective of this sort of testing is to detect security vulnerabilities in client workstation software. Its primary aim is to identify and exploit software vulnerabilities in client-side applications.

Examples include web browsers (Google Chrome, Mozilla Firefox, Safari), office productivity applications, etc.

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Pen Test Lifecycle: How are Penetration Tests conducted?

Typically, penetration testers begin by acquiring as much information as possible about the target. Then, they detect potential system weaknesses through scanning before commencing a controlled assault.

After an assault, they analyze each vulnerability and the associated risk. The penetration test concludes with a comprehensive report to higher authorities summarising its findings.

Depending on the company and the type of penetration test, penetration testing can be divided into different phases.

Reconnaissance & Planning

The planning phase comes first. Here, the attacker gets as much information as possible on the target. The information may include IP addresses, domain information, mail servers, network topology, etc.

Here, the scope of the test is determined, as are the target system and the testing methodologies to be employed.

A competent penetration tester will devote most of their time to this step, aiding subsequent phases of the assault.


The attacker will engage with the target to find vulnerabilities using the information gathered in the first stage. This allows a penetration tester to perform attacks utilizing system weaknesses.

This step involves the utilization of instruments such as port scanners, ping tools, vulnerability scanners, and network mappers.

The scanning portion of web application testing might be either dynamic or static:

  • Static Scanning: Aims is to discover susceptible routines, libraries, and logic implementation.
  • Dynamic Scanning: The tester passes different inputs to the target program and records the outcomes

Actual Exploit

This is a crucial step that must be executed with attention. This is the phase where the damage is done. To conduct an assault on the target system, a Penetration Tester must possess specific skills and methodologies.

Using these approaches, an attacker will attempt to get data, infiltrate the system, conduct DoS assaults, etc., to determine the level of vulnerability of a computer system, application, or network.

Risk Analysis & Recommendations

The last objective of the penetration test is to acquire proof of the exploited vulnerabilities. This stage primarily examines the preceding processes and evaluates the current vulnerabilities in the form of prospective threats.

The penetration tester will occasionally make ideas for enhancing security at this stage.

RELATED: Performing a cybersecurity risk assessment

Report Generation

The penetration test results are collected in a comprehensive report during this phase. This report typically contains the following information:

  • Recommendations made in the previous phase
  • General overview of the penetration test
  • Vulnerabilities detected and their associated risk levels
  • Future security recommendations

What Tools are used for Penetration Testing?

Penetration testers utilize a diverse toolset to make penetration testing more rapid, efficient, simple, and dependable. There are several widespread Penetration Testing tools in use today, most of which are either free or open source. Among the most popular penetration testing tools are:

  • Nessus: Is a web application and network vulnerability scanner which can conduct various scans and help a penetration tester identify vulnerabilities
  • Metasploit: packed with various capabilities, Metasploit is an exploitation framework that allows a skilled tester to create payloads and shellcodes and gain access to perform privilege escalation attacks
  • Nmap (short for network mapper): Effectively a port scanner used by testers to scan systems and networks for vulnerabilities by checking for open ports
  • Wireshark: Used to profile network traffic, allowing the testers to analyze network packets
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