Cloud Penetration Testing

What is a cloud penetration test?

A cloud penetration test goes after your cloud tenant the way an attacker would. For most of our clients that means Microsoft: Entra ID, Azure subscriptions, Exchange Online, SharePoint, OneDrive and Teams. We look for information an outsider can pull from your tenant, ways to get initial access, and paths that let a low-privilege user climb to Global Administrator or reach data they should never see. Then we exploit them to prove the impact.

Why test the cloud separately from the network?

Your firewall doesn't protect Microsoft 365. Anyone on the internet can reach your sign-in page, and an attacker who phishes one password or steals one session token lands inside your tenant without ever touching your office network. A network pentest rarely covers this ground.

Cloud identity has its own attack surface, and it looks nothing like a traditional network:

• App registrations and service principals with far more permissions than they need
• Conditional access policies with gaps, exclusions or legacy sign-in methods still open
• Guest accounts nobody remembers inviting, still holding access to shared data
• Automation accounts, runbooks and managed identities that quietly hold admin rights

How does this differ from an M365/Azure Security Assessment?

We offer both, and they answer different questions. Our M365/Azure Security Assessment reviews your configuration against security best practice and hands you a full list of gaps. A cloud penetration test starts from an attacker's position and proves which of those gaps actually lead somewhere. If nobody has ever looked at your tenant, the assessment often makes the better first step. If you want to know what an attacker could actually do, choose the pentest.

What does testing involve?

Cloud tests usually start from an assumed-breach position: you give us a standard user account, because that's exactly what a successful phish hands an attacker. We also check what an outsider with no account at all can learn about your tenant. From there we enumerate roles and permissions, hunt for escalation paths, abuse misconfigured apps and automation, and see how close we get to sensitive data and administrative control.

Does Microsoft allow this?

Yes. Microsoft permits penetration testing of your own tenant under its published rules of engagement, and we follow them. Those rules prohibit things like denial-of-service testing and any attack on other customers. We go over them with you during scoping so nothing catches your team off guard.

How long does it take?

Most engagements run one to two weeks. The size of the tenant, the number of Azure subscriptions and whether you want unauthenticated testing, assumed-breach testing or both drive the scope and the price.

Related services and reading

• Michigan penetration testing: how we test organizations across the state, remotely or on-site.
• M365/Azure Security Assessment: a configuration review of your whole Microsoft tenant.
• Active Directory Security Assessment: for hybrid environments that sync on-premises AD to Entra ID.
• How to prepare for a penetration test: a free checklist that walks your team through scope, timing and rules of engagement.