Cloud and Microsoft 365 Security Testing, Including Red Team

Cloud and Microsoft 365 compromises often begin with an identity or a setting, not an exotic exploit. We test your tenants for the weaknesses a threat actor would use, and when you want to measure detection and response, we run a red team exercise.

Cloud and Microsoft 365 testing

  • Identity and access. Privileged roles, conditional access gaps, legacy authentication, multi-factor coverage and stale or shared accounts.
  • Applications and consent. Risky app registrations, over-permissioned service principals and user consent settings that let a malicious app gain access.
  • Email. Forwarding and transport rules, mailbox permissions and protections against phishing and spoofing.
  • Data sharing. Anonymous links, guest access and overshared files in SharePoint, OneDrive and Teams.
  • Cloud infrastructure. Exposed storage, permissive network paths, over-privileged roles and secrets left in configuration.

Assume-breach testing

Rather than start from the outside, we can begin with the access a threat actor would have after one successful phishing email: a standard user account or a compromised workstation. From there we test privilege escalation, lateral movement and access to mailboxes and data, and show you the shortest path to the things you care about.

Red team exercises

A red team exercise is goal-based. We agree an objective, such as reaching a sensitive data set or gaining administrative control, and pursue it using techniques seen in real intrusions, mapped to MITRE ATT&CK. The point is to measure whether your people and tools notice and respond, not only whether a weakness exists. A small group on your side knows about the exercise, so a real response is not triggered by mistake, and we debrief with your defenders afterwards.

How an engagement works

  1. Scope and authorization. Tenants, subscriptions, objectives and limits agreed in writing. For Microsoft 365 testing, a tenant administrator approves our access.
  2. Test. Configuration review combined with hands-on testing, or a goal-based exercise, under agreed rules of engagement.
  3. Report. Findings with evidence, risk and prioritized fixes, in business terms and in technical detail.
  4. Debrief and retest. We walk through the results with your team and check fixes afterwards.

What you receive

  • Executive summary for leadership
  • Technical findings with evidence for each issue
  • Attack paths showing how issues chain together
  • Prioritized remediation guidance
  • For red team exercises, a timeline of what was detected and what was not

Why it matters

Our incident responders investigate Microsoft 365 and business email compromise, so we know which settings matter once an account has been taken over. See Business Email Compromise and Microsoft 365 Investigation and all penetration testing services. Our team has delivered hundreds of assessments, has worked with large enterprises including Fortune 50 organizations, and has experience with HIPAA, FISMA and ISO frameworks and with nation-state and APT-level threat actors.

Book a scoping call

Tell us what you want tested and why, and we will talk through scope, timing and what a useful report looks like for your team. Prefer to write? Email info@core-infosec.com or use the contact form. We reply to form and email enquiries by the next business day.

Penetration testing is performed only with written authorization.