Oct 8, 2024 8:30:00 AM | pen testing Offensive Security Checklist

When thinking about offensive security and how it effects your company and data systems, we look at a lot of information.  But who needs offensive security to supplement their standard cyber security?  Here's a checklist you can take a look at that should answer some of those questions for you. 

1. Regulatory Compliance Requirements

• Does your industry require regular security testing (e.g., PCI-DSS, HIPAA, GDPR, SOC 2)?
• Are there upcoming compliance audits that require evidence of security testing?
• Have you had recent policy or legal changes requiring stronger cyber risk management?

2. Recent Security Incidents or Breaches

• Have you experienced any breaches, attempted hacks, or significant security incidents recently?
• Has your organization suffered from phishing attacks, ransomware, or social engineering exploits?
• Were there any incidents where sensitive data was at risk?

3. Current Security Posture

• Are your security measures (e.g., firewalls, IDS/IPS, endpoint protection) regularly tested?
• Do you have a well-defined incident response plan?
• Are your security teams (internal or external) comfortable with detecting and responding to advanced threats?

4. New or Major System Changes

• Have there been significant changes to your IT infrastructure (e.g., cloud migration, major updates)?
• Have you recently deployed new applications, services, or platforms?
• Are there plans for new technologies or software that may introduce new vulnerabilities?

5. Insider Threat Concerns

• Do you have mechanisms in place to monitor for insider threats or privileged account misuse?
• Are there concerns about employee, contractor, or third-party access that could introduce vulnerabilities?

6. Business and Asset Priorities

• Are critical business operations, intellectual property, or customer data well protected?
• Have you identified high-value assets and data that attackers might target?
• Are there any new partnerships, acquisitions, or expansions that could introduce security risks?

7. Engagement with External Vendors/Third Parties

• Have you recently onboarded new vendors or partners with access to your systems?
• Do you conduct regular third-party risk assessments, and are they up-to-date?

8. Team Capacity and Skill Gaps

• Does your internal team have the skills and tools to identify, respond to, and prevent advanced threats?
• Are you considering augmenting your team with Red or Purple Team exercises to test detection and response capabilities?

9. Previous Penetration Testing Results

• Has it been over a year since your last penetration test or adversarial simulation?
• Did previous tests reveal critical vulnerabilities that have not been remediated?
• Have past results been validated through follow-up tests?

10. Business Risk Tolerance

• Does your organization have a low tolerance for security risk, especially financial or reputational damage?
• Are you proactively testing to prevent disruptions that would harm business continuity?