External Penetration Testing and How to Do It

What is External Penetration Testing

External penetration testing also known as external network penetration testing helps to assess the security organisation’s online presence and evaluate the effectiveness of its public-facing systems.

The primary objective of this testing is to simulate real-world cyber threats originating from anywhere in the world, with ethical hackers acting as external attackers. These experts try to break into external systems like apps, web servers, firewalls, and other internet-exposed components.

The Current State of Data Dependency

In today’s technologically advanced world, organisations heavily depend on data, as well as external-facing applications and other external devices, to effectively carry out their day-to-day business operations. These components play a crucial role in enabling smooth functioning and facilitating various tasks within the organisation. However, procedures and functions can be easily disrupted and create downtime if a strong cyber and information security posture is not in place.

Data is King

Data serves as the foundation for informed decision-making and strategic planning. It provides valuable insights into customer behaviour, market trends and internal processes — helping to identify opportunities and address challenges. External-facing applications on the other hand play a crucial role in enabling organisations to effectively engage with their customers, partners and stakeholders. These applications encompass a wide range of platforms, such as websites, applications, online portals, and security devices.

They serve as vital tools for businesses to showcase their offerings, facilitate transactions, gather valuable customer feedback and cultivate strong relationships with their target audience. However, ensuring the security of both business information and the network devices that store it is of paramount importance.

Organisations must prioritise the preservation of confidentiality, integrity, and availability (CIA) in their systems. This entails the seamless operation of these systems without disruptions and avoiding any exposure to the public. It is imperative to implement robust security measures to protect and secure external web applications and other network devices connected to the external network.

How to Strengthen Your Security Stance

One effective way to assess and strengthen the security posture is through external penetration testing. The process involves simulating real-world cyber-attacks to identify vulnerabilities and potential entry points that malicious hackers could exploit. By conducting these tests, you can gain valuable insights into how their external information systems and network devices may be compromised, allowing them to implement proactive measures to prevent such threats and minimise potential damage.

Start with prioritising your sensitive information

The primary goal of external penetration testing is to prioritise the CIA principles: confidentiality, integrity and availability of sensitive information. By subjecting external-facing applications and network devices to rigorous security assessments and testing, vulnerabilities can be identified before they are exploited by malicious actors. This proactive approach not only helps protect the organisation’s reputation but ensures the trust of customers and stakeholders by maintaining the security of their data.

External Penetration vs Internal Penetration Test

Both external and internal pen testing are essential components of a comprehensive security strategy. Each has specific objectives that identify different vulnerabilities.

Let’s start with external…

External penetration testing plays a critical role in assessing an organisation’s online presence’s security and evaluating its public-facing systems’ effectiveness. The primary objective of this testing is to simulate real-world cyber threats originating from anywhere in the world, with ethical hackers acting as external attackers. These skilled professionals attempt to breach the external systems, which may include applications, web servers, firewalls and other components that are exposed to the internet.

By conducting external penetration tests, you can gain valuable insights into potential vulnerabilities that could be exploited by malicious actors. These tests help identify weaknesses in defences, allowing for remediation efforts to be implemented proactively. The goal is to fortify security measures before malicious individuals discover and exploit these vulnerabilities — thereby reducing the risk of successful external attacks.

Through external penetration testing, organisations can receive recommendations and guidance on how to strengthen their defences effectively. By taking a proactive approach to security, you can create a more resilient environment for their internal networks and protect sensitive data from unauthorised access.

In contrast to external penetration testing, an internal penetration test focuses on simulating the actions of a malicious insider who has trusted access within the organisation’s local perimeter. This type of test aims to identify vulnerabilities and weaknesses in the internal network and systems. The objective is to evaluate the organisation’s ability to detect and respond to an attack from within, such as an employee or contractor with malicious intent.

During an internal penetration test, activities may include gathering information, attempting to access confidential information, compromising passwords, exploiting internal servers, targeting directory services, internal email servers, FTP and SSH servers, and more. By simulating these activities, you can uncover potential security gaps and address them before they can be exploited by a malicious insider.

External Penetration Testing or Vulnerability Scanning?

Both methods contribute to enhancing the security posture of an organisation, but they serve different purposes and offer distinct benefits. Vulnerability Scanning is a process of automated assessment that focuses on identifying known security weaknesses in an organisation’s network and applications. Using specialised software tools, vulnerability scanning scans the network to detect common vulnerabilities, outdated software versions, and misconfigurations that could be susceptible to exploitation.

Unlike penetration testing, vulnerability scanning is often less intrusive and time-consuming, providing a snapshot of the current security state, however, it does not provide a comprehensive assessment of your security posture.

Prioritising External Penetration Testing

Before evaluating the effectiveness of internal systems, it is crucial to emphasise the importance of conducting an external penetration test. This proactive approach enables organisations to identify and address vulnerabilities in their Internet-facing systems, thereby minimising the risk of unauthorised access to internal devices and sensitive information.

By simulating the techniques employed by real-world hackers, external penetration testing assists in pinpointing weaknesses within systems. This comprehensive assessment helps in uncovering potential entry points that malicious actors could exploit to gain unauthorised access or compromise data. By identifying these vulnerabilities before they are exploited, organisations can take proactive measures to enhance their security posture and safeguard critical assets from external threats.

Recommended Approach for External Penetration Testing

To ensure a thorough evaluation of your organisation’s security measures, it is advisable to engage the services of a reputable cyber security consultancy when initiating an external penetration test. This partnership allows you to leverage the expertise and experience of professionals who specialises in identifying vulnerabilities and mitigating potential threats.

When conducting an external penetration test, it is essential to provide the consultants with relevant details about your perimeter systems. This includes domains and IP addresses/ranges associated with your network infrastructure. Sharing this information enables penetration testers to simulate real-world scenarios and perform a comprehensive assessment of your systems’ security.

There are different approaches that can be employed during an external penetration test, the two most common being the “Black Box” and “Grey Box” methods. The “Black Box” approach closely mirrors the techniques used by actual hackers, providing a realistic evaluation of your organisation’s security posture. Testers are given minimal information about your systems, allowing them to use their skills and creativity to identify vulnerabilities. However, this method may have limitations as it can potentially overlook hidden or less obvious vulnerabilities that are not immediately apparent to external actors.

On the other hand, the “Grey Box” approach strikes a balance between realism and information sharing. In this method, organisations provide limited details to the testers, typically focusing on critical areas or systems of concern. By giving some insight into the infrastructure, such as high-value targets or areas that require special attention, you can ensure that testers concentrate their efforts on the most important areas. This approach allows for a more targeted assessment, enabling the identification of vulnerabilities that may have a significant impact on your security.

Enhance Your Security Posture

Strengthen your organisation’s security today by prioritising external penetration testing and safeguarding your critical assets. Not sure where to get started? That’s okay, at least you are ready to make a start.

Risk Crew specialises in external penetration testing to ensure the security of organisations’ perimeter systems. We’ve successfully assisted numerous clients in identifying vulnerabilities and fortifying defences against external threats. If you require an external security assessment, contact us, we’re happy to discuss your testing scope.

Risk Crew