Offensive Security

Real-World Penetration Testing
Find Your Risk Before Attackers Do.

Offensive security assessments for Michigan businesses that surface real risk and give your team the intelligence to defend with confidence.

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Our Mission

Real risk, reduced.

Red Raine Labs brings in-depth offensive testing to small and mid-market organizations. Your IT environment is unique, so we customize our testing approach and prioritize findings based on your actual business risk.

Our Services

Coverage across your critical attack surfaces

Targeted testing across the surfaces that matter most to your business, scoped to your budget and priorities.

Network Penetration Testing

Offensive testing of your external and internal network infrastructure to identify and exploit misconfigurations, weak credentials, unpatched services, and Active Directory weaknesses. Successful exploitation shows exactly how far an attacker gets from an initial foothold, and which issues actually warrant your attention.

Cloud Penetration Testing

We attack your Azure and Microsoft 365 tenant to surface information disclosure, initial access vectors, and privilege escalation paths. Exploiting them proves whether a single compromised account can reach your most sensitive data.

Web Application Penetration Testing

Hands-on exploitation of authentication bypasses, business logic flaws, and data exposure issues in your applications. We chain multiple weaknesses together to demonstrate realistic attack paths and the business impact behind them.

Wireless Penetration Testing

We target encryption weaknesses, guest network segmentation, and rogue access points the way an attacker in your parking lot would. Breaking in proves whether wireless is a legitimate path onto your internal network.

AI Penetration Testing

Adversarial testing of LLM applications, model APIs, and AI-integrated pipelines against the OWASP LLM Top 10. We exploit prompt injection, tool permissions abuse, and downstream systems reached through the model.

Social Engineering & Phishing

Real-world phishing campaigns and social engineering simulations that evaluate your organization's technical security controls and human security defenses and provide metrics on employee awareness and susceptibility.

Vulnerability Scanning & Assessment

Systematic identification of known vulnerabilities across external and internal infrastructure, web applications, and cloud environments. Provides the baseline assessment needed for initial risk visibility and remediation prioritization.

M365/Azure Security Assessment

Configuration-focused audit to identify security and compliance gaps across the Microsoft suite, including Entra, Azure, SharePoint, and integrated services. Ensures proper identity management, data protection, and alignment with organizational security policies.

Active Directory Security Assessment

Focused assessment of on-premises and hybrid Active Directory. We map domain and trust relationships, privilege escalation paths, Kerberos and delegation weaknesses, GPO and ACL misconfigurations, and tiering gaps that adversaries abuse to reach Domain Admin and persist undetected.

Our Approach

Why Red Raine Labs

Anyone can hand you a list of vulnerabilities. We exploit them, chain them, and show you which ones actually threaten the business.

Real Attack Paths

We chain weaknesses the way an attacker would and safely exploit them, showing the full path from initial foothold to your critical data and systems.

Validated Findings

A certified penetration tester confirms and prioritizes every finding, translating technical issues into clear business impact.

Remediation You Can Act On

Every finding ships with a specific, prioritized fix. Each finding comes with practical guidance your team can execute, not generic advice copied from a scanner.

Get Started

Start Your Penetration Test

Discuss your security needs and how we can help reduce business risk and strengthen resilience.

  • Scoped to your budget and priorities
  • Findings translated into business impact
  • Direct line to the tester doing the work

We typically respond within one business day.