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7 Tips for Conducting a Successful Penetration Test

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A penetration test, also known as a pentest, is an authorized simulated attack on a computer system or network to find security vulnerabilities. Organizations need to conduct regular penetration tests to identify and fix security flaws before they can be exploited by malicious actors. In this blog post, we will share seven tips for planning and conducting a successful penetration test, from defining your critical assets, scope, and methodology to planning for re-testing and finding an experienced penetration testing provider.

1. Identify your critical assets

The first step in conducting a successful penetration test is to identify your organization’s critical assets. This includes any systems or data that, if compromised, could result in the following:

Serious financial loss

What critical assets could an attacker exploit to cause serious financial loss for your organization? Is it customer data? Payment card data? Proprietary information? Identify the systems and data that are most important to your business, and make sure they’re also included in the scope of your penetration test.

Regulatory penalties

Are there any industry-specific regulations that apply to your organization? If so, you’ll need to make sure your penetration test covers any compliance requirements. For example, if you’re a healthcare organization subject to HIPAA, you’ll need to ensure that your penetration test includes an assessment of the security of any ePHI data.

Reputational damage

Is there any system or data type that, if compromised, could damage your organization’s reputation? For example, if you’re a social media platform and an attacker gains access to customer data, that could have a serious impact on your brand and reputation.

Operational disruption

What systems and data are critical to your organization’s operations? For example, if you’re a manufacturing company, an attacker who gains access to your production control systems could cause significant disruption.

Prioritizing your assets will help you determine the scope of your penetration test.

2. Define your scope and approach

The scope should include all systems and data that could potentially be accessed or compromised by an attacker. This will help you focus your testing efforts and resources on the most important assets. Defining your scope should include the following:

Targets

What networks, applications, and devices do you want to include in the scope of your penetration test? Among the typical security testing targets for a penetration test are the following:

Boundaries

The boundaries of your penetration test should state what is included and what is out-of-scope for testing. For example, if you’re testing an external network perimeter, your boundaries might include all public-facing IP addresses. If you’re testing a web application, your boundaries might include all URLs and input fields.

Depth of assessment

Is your penetration test focused on exploring one system or exploit in detail, or do you want a more comprehensive assessment of all systems and data in scope? The depth of your assessment is often determined by the time and resources you have available.

The methodology includes three main approaches to penetration testing:

Black-box testing

Black-box testing is when the penetration tester has no prior knowledge of the system or network being tested. This is the most common type of penetration test, as it simulates an attacker who knows nothing about your organization or systems. Black-box testing has the advantage of being more realistic, but it can also be more time-consuming and expensive.

White-box testing

In contrast, white-box testing is when the penetration tester has full knowledge of the system or network being tested. This type of penetration test is less common, as it requires the tester to have a deep understanding of your organization’s systems and data. Although white-box testing is comprehensive by nature, its main downsides are that it’s less realistic and can be more expensive.

Gray-box testing

Gray-box testing is a hybrid of black-box and white-box testing, where the penetration tester has some knowledge of the system or network being tested. This type of penetration test is a good compromise between realism and comprehensiveness. as it’s more efficient and cost-effective than white-box testing.

3. Harden your systems

Before you conduct a penetration test, it’s important to harden your networks and systems. This means ensuring that they are configured securely and that all security controls are in place and functioning properly. This will help prevent attackers from exploiting any vulnerabilities that are found during the test.

Hardening your systems can include the following steps:

Reviewing your networks and system configuration

A system and configuration review consists of auditing your networks and systems to ensure that they are configured securely. This can be done manually or with the help of automated tools.

Applying security patches and updates

It’s important to keep your systems up-to-date with the latest security patches and updates. This will help close any known vulnerabilities that could be exploited by attackers.

Enabling security features

Enabling security features such as firewalls, intrusion detection/prevention systems, and encryption can help protect your systems from attack.

Implementing access control measures

Restricting access to systems and data to authorized users only can help prevent unauthorized access and reduce the chances of a successful attack.

4. Set a testing frequency

Depending on the size, resources, and security objectives of your organization, setting a bi-annual or annual penetration test may be appropriate. However, if your systems include a high-risk environment or are subject to compliance requirements, more frequent and modular testing may be necessary. A high-risk environment could include critical infrastructure or systems, such as a hospital or nuclear power plant. A compliance requirement could be the Payment Card Industry Data Security Standard (PCI DSS), which requires quarterly penetration testing for organizations that process credit card transactions.

Partnering with an experienced penetration testing provider can help you determine the appropriate testing frequency for your organization.

5. Plan for a vulnerability re-test

For your penetration test to be truly successful, you’ll need to plan time and resources for fixing the vulnerabilities identified during the test. Once the penetration test is complete, your organization will be provided with a report that includes a list of vulnerabilities and recommendations for remediation. The remediation process can be time-consuming and resource-intensive, so it’s important to plan for it in advance.

The remediation process typically includes the following:

  • Assessing the risk of the vulnerabilities found.
  • Identifying who will be responsible for fixing each vulnerability.
  • Prioritizing your remediation efforts.
  • Implementing the fixes or remediating controls.
  • Re-testing the fixes to ensure they are effective.

6. Find a qualified testing provider

Not all penetration testing providers are born equal. Identifying an experienced and qualified penetration testing provider comes down to the following steps:

  • Ensuring the provider is 100% dedicated to penetration testing and formally certified for quality management standards, such as ISO9001.
  • Asking about the firm’s experience and reputation, i.e., number of projects delivered, recurring projects, and customer testimonials.
  • Checking if they have a certified team, made of real-world experienced and industry-certified consultants (OSCP, OSWE, GWAPT, GPEN, OSEP, etc.).
  • Making sure the provider isn’t reselling hardware or software solutions, thus providing expert services with impartiality.
  • Confirming that your project will be carried out in-house by a team of specialists, avoiding outsourcing of any kind, thus ensuring quality consistency.
  • Verifying that the provider’s standards and methodologies are following best practices and key standards in the penetration testing industry (OSSTMM, OWASP, NIST, CVE, CVSS, STIX, CAPEC, etc.).

Wrapping up

Ensuring your penetration testing project is a success might seem like a daunting task, but following these tips will go a long way in keeping it simple, from scoping to re-testing. And penetration testing for network security or data security compliance doesn’t have to be a lonely journey. Getting started with some cost-effective Q&As with a professional pentester could help you get more done, in less time, with no waste of time or resources. Because, when it comes to testing the security of your critical assets and client data, there’s no compromise on quality possible: It needs to be 100% tested for security.

Contact us If you need help with your penetration testing project.

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