As the year starts, an organization should assess its cyber posture while ensuring its pentesting measures are on par. Periodic pentesting should be a part of the security matrix of an organization to pre-emptively eliminate potential attack vectors. Nevertheless, it’s not a “set and forget” activity since it requires change management and refinement.

This blog will offer key guidance to improve an organization’s security framework and embrace the new normal. We will cover the following topics:

• The importance of regular evaluation for pentesting measures.
• Pentesting strategy optimization.
• Pentesting trends and methodologies are on the rise.
• Incorporating pentesting into a continuous security program.

Why Annual Pentesting Evaluation Is Crucial

Cyber-attacks are ever-changing, with new vulnerabilities being created in applications, networks, and cloud environments, which means that today’s security measures will be completely useless against tomorrow’s threats. Regular evaluation for pentesting ensures that these threats are neutralized and the vulnerabilities accepted over the past year have been resolved. Important reasons to pentest routinely are:

• Identify New Vulnerabilities: Software changes, new infrastructure, and updates lead to the discovery of other exploits and threats that require security assessments.
• Regulatory Compliance: Numerous business verticals are required to undergo periodic protection testing as a conformance measure to business standards like PCI DSS, HIPAA, and IS0 27001.
• Improve Incident Response Readiness: Regular pentesting determines the efficiency of security teams in addressing the effectiveness of their responses to pre-planned attacks.
• Enhance Security Posture: Data breaches and cyber-attacks are less likely to occur when there is proactive security, along with consistent testing.

Emerging Trends and Methodologies in Pentesting

Organizations must remain on top of newly developed threats, as the cyber security world is forever changing. Here are some emerging shifts in pentesting for the year 2025:

1. Cloud Security Pentesting
With so many organizations moving to the cloud, the strategies in pentesting need to change to meet the requirements for testing cloud architectures. Some major points of interest include:

• IAM misconfiguration: Ensuring user role provisioning follows the principle of least privilege.
• Storage Security: Preventing uncontrolled data exposure.
• Test the security of serverless components, e.g., AWS Lambda, Azure Functions, and Google Cloud Functions.

2. API Security Testing
APIs in most applications have become integral parts, and API security testing cannot be ignored. Common vulnerabilities in APIs are:

• Broken authentication and authorization.
• Injection attacks (SQLi, XSS, XML, etc.).
• Insecure data exposure.

3. Adversary Simulation and Red Teaming
Red team operations shouldn’t be confused with pentesting as it simulates real-world attacks. This method investigates if an organization can address advanced persistent threats or APTs. Important methods include:

• Re-enactment of phishing attacks to check user vigilance.
• The lateral movement attempts to evaluate the security of the internal network.
• Escalation attempts to test the identity access management processes.

Key Steps to Optimize Your Pentesting Strategy

To maximize the effectiveness of pentesting efforts, organizations should follow a structured approach. Here are some best practices to enhance pentesting in the new year:

1. Define Clear Objectives and Scope
Before launching a pentest, it is crucial to establish clear objectives and define the scope. This ensures the test focuses on high-risk assets and aligns with business priorities. Organizations should:

• Identify critical assets and potential attack vectors.
• Determine the type of testing needed (e.g., web application, network, API, mobile, cloud).
• Set clear goals, such as assessing privilege escalation risks or testing for specific OWASP Top 10 vulnerabilities.

2. Latest Testing Methodologies
Pentesting methodologies should evolve alongside cybersecurity threats. Organizations should leverage frameworks such as:

• MITRE ATT&CK: Maps attacker tactics, techniques, and procedures (TTPs) to real-world scenarios.
• OWASP Testing Guide: Focuses on application security best practices.
• PTES (Penetration Testing Execution Standard): Covers the entire pentesting lifecycle.

3. Leverage Automated and Manual Testing
Automation can help identify common vulnerabilities efficiently, while manual testing provides deeper insights into complex attack scenarios. A balanced approach consists of the following components:

• The use of Dynamic Application Security Testing (DAST) and Static Application Security Testing (SAST) tools to facilitate automated scans.
• Manual exploitation tests to identify business logic attacks, privilege escalation, and other complex attack methods.

4. Prioritize and Remediate Findings
Once vulnerabilities are found, every entity should prioritize fixing them depending on how severe and impacting they are. A structured approach includes:

• Assigning a level of risk to the vulnerability defined as critical, high, medium, and low.
• Fixing that involves the application of patches, security updates, and configuration changes.
• Retesting to confirm the fixes.

How to Integrate Pentesting into a Continuous Security Program

Most organizations focus on pentesting only once a year, but it should be a part of secure continuous programs. So, how can organizations make this ongoing:

1. Adopt Pentesting as a Service (PTaaS)
PTAAS gives the flexibility of doing on-demand testing almost any time without waiting due to the collaterals that come with traditional testing/ engaging methods. Its advantages include:

• Possible interaction with pentesters in between.
• Allowing non-stop vulnerability assessments.
• Shorter cycles for troubleshooting.

2. Implement DevSecOps Practices
Security must be part of the SDLC pipeline. This enables organizations to:

• Implement SAST and DAST tools in their CI/CD pipelines.
• Perform secure code assessments before deployment.
• Scan for vulnerable components from 3rd parties.

3. Regularly Train Security and Development Teams
A trained personnel or team acts as the first line of defense against repeated cyber-attacks by most organizations. Therefore, organizations should:

• Provide security awareness courses.
• Training in the form of real-life pentesting workshops.
• Foster CTF (Capture the Flag) contests for enhanced competitive skills.

Conclusion

A new year means an opportunity to fortify the perimeter by improving penetration testing strategies. With the utilization of a methodology that embraces and utilizes the latest trends in a business’s continuous security framework, it is possible to conduct penetration testing in a manner that will detect and identify vulnerabilities ahead of time.

The use of automated and manual tools, as well as red teaming, is becoming standard practice in businesses. With this variety of available tools, businesses can easily keep track of ever-evolving threats. Given the increasing complexity of cyberattacks, companies must adopt a strong cyber resilience strategy supported by a well-defined approach to penetration testing.

Strengthen your cyber resilience and stay ahead of evolving threats. Explore how Cobalt's modern penetration testing solutions, combining automated tools, expert manual testing, and red teaming, can secure your business for the year ahead. Request your demo today!