How to Future-Proof Your IT Environment Before Microsoft Ends Support in October 2025
Key Points
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Penetration testing assesses system and network vulnerabilities, identifying potential attack vectors prior to their exploitation by malicious actors. - Security and compliance frameworks such as NIST CSF, CIS Controls, PCI-DSS, and HIPAA often require or recommend regular penetration testing.
- Organizations should integrate annual, quarterly, or monthly penetration tests into their cybersecurity strategies to meet compliance requirements and, more importantly, stay ahead of evolving threats.
Why Regular Penetration Testing is Critical for Cyber Resilience
Are you confident that your current security controls protect your company’s most valuable cyber assets? Far too many companies still believe their company is not a target, but we have unfortunately seen attacks on companies of all sizes. So, you can be certain that if your company has data or systems that are valuable to you, you have something of value to attackers and you are a target. Also, many organizations underestimate the ease with which malicious actors can identify targets and vulnerabilities using automated tools and scripting. Therefore, organizations must continuously assess their security posture to stay ahead of adversaries. Regular penetration testing is one of the most effective ways to identify and address weaknesses in your security controls.
Identifying Weaknesses Before Attackers Do
A penetration test simulates real-world cyberattacks without causing actual harm, uncovering vulnerabilities before they can be exploited. By systematically evaluating network security and access controls, organizations can identify weaknesses and develop plans for reducing associated risks.
Regulatory Compliance & Risk Reduction
Security and compliance frameworks such as NIST CSF, CIS Controls, PCI-DSS, and HIPAA recommend or require at least annual penetration testing. While conducting penetration tests helps meet the requirements, the greatest value comes from minimizing risks to the environment by identifying vulnerabilities and potential attack points and then providing remediation guidance. In other words, it’s not just about checking a compliance box, but actually reducing risks in the environment.
Controlling Insurance Premiums Through Penetration Testing
Cybersecurity insurance carriers often assess the risk profile of an organization based on its cybersecurity measures. By conducting periodic penetration tests, organizations can reduce the likelihood of costly breaches and incidents, which in turn can lead to lower insurance premiums.
Strengthening Incident Response
Beyond identifying vulnerabilities, penetration tests help validate intrusion detection tools and incident response capabilities. Understanding how systems respond under simulated attack conditions equips security teams with the knowledge to improve detection and recovery processes.
Final Thoughts: Make Penetration Testing a Routine
While best practice and compliance frameworks recommend at least annual penetration tests, quarterly or monthly testing can provide more real-time insights to help secure your infrastructure. Therefore, you should strongly consider adding annual, quarterly, or monthly penetration tests as a key component of your cybersecurity strategy. Additionally, penetration tests should be completed after any updates or changes to the environment to ensure new vulnerabilities are not introduced. As new threats emerge, organizations that prioritize continuous security validation will be positioned to efficiently and effectively mitigate risk and safeguard critical assets.
Keller Schroeder’s offerings in this category range from comprehensive Vulnerability and Penetration Assessments to PTaaS (Penetration Testing as a Service), meeting a wide range of budgets and risk reduction appetites. So, please reach out if you have any questions or want to learn more!
