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Complete Guide to Penetration Testing

With the increasing cyber attacks in recent years, organizations have started focussing on security features of software applications & products. Despite, applying sincere and attentive efforts towards the development of safe and secure software applications, these software products gets lack into one or more than one security aspect or feature, owing to various tangible and intangible errors. Thus, it has become essential to explore each and every vulnerable area present in the application which may invite and provide opportunity to hackers and crackers in exploiting the system.

What is Penetration Testing?

Penetration testing is one of the useful testing methodologies to identify and reveal out vulnerable areas of the system, which may provide passage to number of unauthorized and malicious users or entities for intruding, attacking and compromising the system’s integrity & veracity.

The process of penetration testing involves the wilful and authorized attacks on the system in order to identify and spot the weaker areas of the system including security loopholes and gaps, vulnerable to multiple security threats and attacks. These revelations help in fixing various security bugs and issues in order to improve and ameliorate the security attributes.

In addition to its defined objectives, penetration testing approach may also be used to evaluate and assess the defensive power mechanism of the system; how strong or capable is the system to defend different types of unexpected malicious attacks?

What are the Reasons for System’s Vulnerabilities?

Number of activities contributes towards the occurrence of security vulnerabilities in the system such as:

  • Designing Error: Flaws in the design may be seen as one of the most prominent factors for the occurrence of security loopholes and gaps in a system.
  • Configurations and settings: Sometimes, inappropriate setting and configuration of associated hardware and software may results in introduction of vulnerabilities in the system.
  • Network Connectivity: Safe and secure network connection prevents the incident of malicious and cyber attacks, whereas insecure network provides gateway to hackers for assaulting the system.
  • Human Error: To err is human; Mistakes committed intentionally or unintentionally by the individual or by the team, while designing, deploying or maintaining system or network may also lead to occurrence of security glitches in the system.
  • Communication: Improper and open communication of confidential data and information amongst the teams or the individual using internet, phone, mail or any other mean also leads to security vulnerabilities.
  • Complexity: It is easy to monitor and control security mechanism of a simple & sober looking network infrastructure, whereas it is difficult to trace leakages or any malicious activity in the complex systems.
  • Training: Lack of knowledge and training over security to both in-house employees and those functioning outside the organizational boundary, could also be seen as one of the prominent factors of security vulnerabilities.

Is Penetration Testing = Vulnerability Assessment?

No, penetration testing and vulnerability assessment are two different approaches, but with the same end-purpose of making software product/system safe and secure.

People are often ambiguous between the differences or similarity between these two techniques and use them interchangeably. However, both methodologies have different workflow to ensure the safety and security of the system.

Penetration Testing is a real time testing of the system, where the system and its related component are thrashed by the simulated malicious attacks in order to reveal out security flaws and issues present in it. It may be carried out using both manual approach and with the help of automation tools. While, Vulnerability Assessment involves study and analysis of system with the help of testing tools to identify and detect security loopholes and flaws present in the system and making it vulnerable to multiple variants of security attack.

Vulnerability Assessment methodology follows a pre-defined and established procedure, unlike penetration testing where the sole purpose is to break system, irrespective of adopted approaches. Through, vulnerability assessment, vulnerable areas are being spotted which may provide opportunity to hackers to attack and compromise with the system. Further, various remedial measures are provided in the approach of vulnerability assessment to remove or correct the detected flaws.

Why Penetration Testing?

As stated earlier, security loopholes, gaps and weakness prevailing in the system provides doorway to unauthorized user or any illegal entity to attack and exploit the system affecting its integrity & confidentiality. As such, penetration testing of software products has become the necessity to get rid of these vulnerabilities in order to make system competent enough to get protected and survived of expected and unexpected malicious threats and attacks.

So, let’s go through and recall the need of penetration testing in below given points:

  • To identify weaker and vulnerable areas of the system before the hacker spots it.
  • Daily, frequent and complex upgrades to make your system up-to-date may affect the associated hardware and software, resulting into security issues. As such, it is pertinent to monitor and control these upgrades to avoid any kind of security flaws in the system.
  • As discussed earlier, it is preferred to evaluate the current and existing security mechanism of your system in order to assess its competency in defending or surviving unexpected malicious attacks. This ensures the level of security standards maintained in the system along with the confidence in the system’s security traits.
  • Along with the system’s vulnerabilities, it is recommended to assess different business risks and issue including any sort of compromise with organization’s authorized and confidential data, with the help of business and technical team. This helps organization to re-structure and prioritize their plans and execution in order to avoid and mitigate different business risks and issues.
  • Last, but not the least, to identify and meet certain essential security standards, norms and practices, a system is lacking or is deficient of.

How to perform penetration testing?

Penetration testing of a system may be carried using any of the following approaches:

  • Manual Penetration Testing.
  • Automated Penetration Testing.
  • Manual+Automated Penetration Testing.

1. Manual Penetration Testing:

To carry out the manual penetration testing of a software product, a standard approach involving following operations or activities is being followed in a sequential manner:

  • Penetration Testing Planning:Planning phase involves the gathering of requirements along with the defining of the scope, strategies and objectives of the penetration testing in adherence to security standards and norms. Further, this phase may include the assessment and listing of areas to be tested, types of testing to be performed, and other related testing activities.

Scope may be defined using following criteria:

  • Reconnaissance:This phase involves the gathering and analysis as much as detailed information as possible about the system and related security attributes, useful in targeting and attacking each and every corner of the system to carry out effective and productive penetration testing of the system.Reconnaissance involves two different forms of gathering and analysing targeted system’s information; passive reconnaissanceand active reconnaissance, where former involves no direct interaction with the targeted system, and the latter approach needs direct interaction with the system.
  • Vulnerability Analysis:During this phase, vulnerable areas of the system are being identified and detected by the tester to get entry into the system and initiate the task of attacking the system using penetration tests.
  • Exploitation:This phase may be seen as the actual penetration testing of the system, where both internal and external attacks are being carried out, compromising both internal and external interfaces of the system.
    • External attacks are the simulated attacks from external world perspective, prevailing outside the system/network’s boundary. This may include gaining illegal or unauthorized access to system’s features and data pertaining to public facing applications and servers.
    • Internal attacks may be seen as those attacks which already intruded the system & got access to network perimeter, and carrying out various malicious activities to compromise with system’s integrity and veracity. This attack is useful from the purpose that those authorized entities within the network perimeter may intentionally or unintentionally compromise with the system.
  • Post-Exploitation:After exploiting the system, the next step is to perceive and analyse each and every different attacks on the system independently from different perspectives to assess the purpose and objective of each different attack along with its potential impact on the system and the business process.
  • Reporting: Reporting task involves the documentation work of the activities carried out prior to this phase. Further, reporting may also include different risks and issues identified, vulnerabilities identified and detected, all vulnerable areas whether exploited or not and remedial solutions to correct identified flaws and issues.

2. Automated Penetration Testing:

Another useful & effective approach of performing penetration testing is with the help of penetration testing tools. In fact automated penetration testing is very faster, speedy, reliable, convenient, and easy to execute & analyse approach. These tools are efficient in precisely and accurately detecting the security defects present in the system in a short period of time along with the delivery of crystal-clear reports.

Some of the popular and widely used penetration testing tools are:

  • NMap.
  • Nessus.
  • Metasploit.
  • Wireshark.
  • Veracode; and many more.

However, it is preferred and recommended to select tool based on below given criteria to meet each different requirements.

  • The tool should be easy to deploy, use and maintain.
  • Supports easy and quick scan of the system.
  • Able to automate the process of verifying the identified vulnerabilities.
  • Able to verify the previously detected vulnerabilities.
  • Feature of producing crystal clear, yet simple and detailed vulnerability reports.

3. Manual + Automated Penetration Testing:

A better approach of two combine the pros of manual and automation to ensure effective, monitored, controlled, reliable, precise and accurate penetration testing of software product in quick and speedy manner.

Types of Penetration Testing:

Depending upon the elements and objects involved, penetration testing may be categorized into following types:

  • Social Engineering Test: This test involves the usage of ‘human’ element to astutely reveal & gain the confidential & sensitive data and information over internet or phone from them. These may include employees of the organization or any other authorized entity present within the organization’s network.
  • Web Application Test: It is used to detect security flaws and issues in multiple variants of web applications and services hosted on client or server side.
  • Network Service Test: This involves the penetration testing of a network to identify and detect the security vulnerabilities, providing passage to hackers or any unauthorized entity.
  • Client Site Test: As the name suggest, this test is used to test applications installed at client site.
  • Remote Dial-up Test: Testing the modem or similar object which may provide access to connected system.
  • Wireless Security Test: This test targets the wireless applications and services including its different components & features such as routers, filtering packets, encryption, decryption, etc.

We may also categorize penetration testing based on the testing approaches to be used as stated below:

  • White Box Penetration Testing: In this approach, tester will have complete access to and in-depth knowledge of every minute and major attributes of system, in order to carry out the penetration testing. This testing is very much effective in comparison to its counterpart; white box approach, as the tester will be having complete and in-depth knowledge and understanding of each and every aspect of the system, useful in carrying out extensive penetration testing.
  • Black Box Penetration Testing: Only high-level of information is made available to testers such as URL or address of the organization to perform penetration testing. Here, tester may see himself as a hacker who is unaware of the system/network. Black box testing is a time consuming approach as the tester is not cognizable of system/network’s attributes and he/she will need considerable amount of time to explore system’s properties and details. Further, this approach of testing may result into missing out of some areas, keeping in view limited time period and information.
  • Gray Box Penetration Testing: Limited information available to testers to externally attack the system.

Penetration Testers:

The professionals or the individuals who proceeds and execute the task of penetration testing are called penetration testers. His/her job is to identify, locate and demonstrate the security flaws, loopholes and deficiencies present in the system.

In case of manual penetration testing of the application, the responsibilities of penetration testers increases manifold times. As such, it is essential and pertinent to state some of the characteristics and responsibilities of a penetration tester.

Characteristics and Responsibilities of a Penetration Tester:

  • A Penetration tester should be very much inquisitive to trace and explore each and every corner of the system/network.
  • He/she should be aware of & have hacker’s mindset.
  • He/she should able to identify and detect different components and areas of the system, which may be seen as the prime targets of hackers.
  • A penetration tester should be skilled and proficient in reproducing bugs or defects identified by him/her in order to assist developers in fixing them.
  • Penetration tester will have full access to each and every component of the system including confidential data and information, and thus it is expected from them to keep these data & information confidential and secure. He/she will be fully responsible for any sort of compromise, damage or loss to system’s data & information.
  • He/she should be well-proficient in communication to convey & report vulnerabilities, their details and other related information in clear, precise and effective manner to related teams.

Penetration Testing Limitations:

Amidst its various positives, penetration testing is affected by some limitation as stated below:

  • Limited time and increased cost of testing.
  • Limited scope of testing based on the requirements in the given period time, which may results into overlooking of other critical and essential areas.
  • Penetration testing aka pen testing may break-down the system or put system into failure state.
  • Data is vulnerable to loss, corruption or damage.


Advancement in technologies has armed hackers with wide variety of resources and tools to easily break into system and network with the intention to cause loss to you or your organization name, reputation and assets. More than the testing, pen testing may be seen as a precautionary approach to identify and detect various symptoms of security deficiencies in order to nullify the potential security threats to system.

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