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?