Art of External Network Penetration Testing – Phase First: Preparation


With the rapidly developing technologies in the digital world, the security measures of organizations are constantly evolving. This evolution makes proactive security measures such as “external network penetration testing” more important, especially to ensure the security of external networks and systems. In this article, we will focus on a critical phase of this type of testing: the preparation phase. This phase lays the groundwork for cybersecurity experts to securely test an organization’s external networks.

External network penetration testing is performed to assess how resilient organizations are to attacks. However, this assessment must be carefully planned before it begins. The preparation phase includes steps such as determining the scope of the test, obtaining permissions, reviewing security controls and coordinating the testing process. This phase gives the cybersecurity team the opportunity to understand the purpose of the test and perform it effectively.

In this article, we will examine the preparation phase of external network penetration testing in detail. We will focus on what steps should be taken, why this phase is critical, and how organizations can strengthen their cyber defenses.

This article covers in detail the preparation phase of an external and web application security penetration test. The balanced approach and level of knowledge between the steps clearly reflects that this is a gray-box penetration test. Sharing information about the overall architecture of the applications to be tested provides the test team with an inside view, but does not disclose all the details.


This process requires a detailed preparation phase. Steps such as setting objectives, obtaining permissions, defining the test scope and evaluating security controls ensure that a pentest can be conducted in an effective and controlled manner. However, the needs of each organization are different, and therefore this preparation process must be tailored to the specific requirements.

Recommended steps:

In order to carry out a planned pentest, it is crucial to address the key steps here.

  • Goal setting and scope definition:
    • Clearly define the test scope. Determine which IPs, domains and services will be available within the test
  • Permission and Notifications:
    • Obtain the necessary permissions for Pentest. Some IP addresses or domains may be more risky than the average. Do not underestimate the attack power and functional risks in API testing.
  • Collection of Sources:
    • Gather detailed information about the applications. This includes the architecture of the application, the architecture of the services, the purpose of the external services that are active, etc.
  • Application Mapping:
    • Map web applications to understand page structures, entry points and data flows.
    • Identify critical points within the application, considering how an attacker can reach the target.
  • Identify Security Audits and Controls:
    • Identify the existing security controls and controls of the applications. Classify and identify applications where WAF (Web Application Firewall) systems are not identified.
    • Using vulnerability scanning tools directly may miss protected applications.
  • Preparing the Test Environment:
    • It is important to prepare your working environment for testing and to work actively and efficiently. Isolate your test environment well to minimize the risk of damage to the production environment.
    • If necessary, position a product in the operating system for source code analysis of the organization’s product. Open the source code with the help of an IDE.
  • Collaboration with the Security Team:
    • Communicate regularly with application owners and the security team. Share potential issues and expectations in a coordinated way.
    • Apps can become unresponsive, the app can go into maintenance, it is important to reactivate them.
  • Defining a Test Account:
    • In external applications, an authorization system may be available. By defining accounts with authorizations such as Moderator, Admin, User, prepare to check the authorizations of each of them.
  • Create a Pentest Plan:
    • Create a detailed plan for the test. Determine the steps of the penetration test to be performed, this can be a checklist. Make a copy of this checklist and expand it by adding it to your methodology plan.
    • Prepare the necessary pentest tools. Entering the API keys of the tools is turning the tool from gold to diamond. Remember to integrate API keys for efficient testing.
  • Move Forward With Notes:
    • Even in a penetration testing process or a zero-day researcher, it is of utmost importance to constantly take notes. Don’t you want to know where your path might lead?
  • Follow the sources
    • Integrate rich resource into your own roadmap. Add ideas to your ideas with constantly updated and open source projects.
  • Reporting Plan:
    • Develop a reporting plan for test results, specifying the required information, ensuring accurate transmission to the organization, and establishing the reporting date.


External and web application security penetration tests are an essential step in building a proactive defense strategy against cyber threats. These tests are designed to assess security controls, identify existing vulnerabilities, understand attack vectors and make the organization’s digital assets more secure. However, taking the right preparatory steps is critical for this process to be carried out effectively.

The steps detailed above include the key elements that should be followed prior to an external and web application security penetration test. Each step provides an opportunity to identify and remediate vulnerabilities. However, this process is just the beginning; a truly effective cybersecurity strategy should include continuous monitoring, updating and training.

It should not be forgotten that cyber threats are constantly evolving and developing. Therefore, pentesting processes should also be dynamic and flexible, allowing organizations to continuously revise their security strategies and make improvements. This will make organizations better prepared for future cyber threats and allow them to manage their digital assets more securely.

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