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First Harbor Bank: cloud sign-in that survives the datacenter going dark

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First Harbor Bank: cloud sign-in that survives the datacenter going dark

First Harbor Bank's Azure tenant is synchronized from on-premises AD DS via Microsoft Entra Connect for 3,000 users. Regulators require that Microsoft 365 sign-in continues if the on-premises datacenter is offline, that no inbound connections from Azure to the on-premises network are required, and that a legacy intranet application using Kerberos keeps working for domain-joined PCs. Forty people hold privileged roles, all currently as permanent Global Administrator assignments. Auditors want every privileged activation logged and retained for one year, and want evidence that a compromised administrator account cannot lock the tenant out.

1. Choose between password hash synchronization, pass-through authentication, and federation. Justify against all three constraints, including the Kerberos requirement.

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Password hash synchronization plus seamless SSO.

  • Federation (AD FS) requires inbound connectivity from clients to on-premises STS and dies when the datacenter is offline. It violates both the resilience and the no-inbound constraints. Eliminated.
  • Pass-through authentication uses outbound-only agents, so it satisfies the no-inbound rule, but authentication is validated on-premises. Datacenter offline means no sign-in unless PHS is also enabled as a fallback. It does not meet the resilience requirement on its own.
  • PHS validates credentials in the cloud. The datacenter can be dark and Microsoft 365 sign-in continues. Microsoft syncs a hash of the hash, not plaintext, which is acceptable to most regulators.
  • Kerberos nuance: the legacy intranet app needs a Kerberos ticket from a domain controller, so it depends on-premises regardless of the sync method. Seamless SSO gives domain-joined PCs single sign-on to Entra ID resources without re-prompting, and it is what makes the hybrid experience tolerable - but be precise with the auditors: cloud sign-in survives a datacenter outage; the on-premises intranet application does not, and no identity configuration changes that.
  • Keep PTA agents deployed as a standby only if policy demands it; PHS remains the primary.

2. Redesign privileged access so activations are time-bound and audited, and so a compromised administrator cannot lock the tenant out.

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Eligibility over assignment, separation over convenience, and a break-glass path outside the system.

  • PIM. Convert all 40 permanent Global Administrator assignments to eligible assignments: approval required, justification, MFA or a phishing-resistant authentication strength at activation, maximum activation of 4 hours, and notification to the security team.
  • Reduce standing access. Global Administrator should be a handful of people; move the rest to narrower roles (User Administrator, Application Administrator, Exchange Administrator). Use access reviews quarterly - 40 permanent GAs is an audit finding on its own.
  • Separate admin identities. Cloud-only accounts with no mailbox and no synchronization path, used only from privileged access workstations. A compromised synced account should never be an admin account.
  • Conditional Access on directory roles: compliant or PAW device, authentication strength requiring FIDO2, block legacy authentication, restrict session lifetime.
  • Break-glass. Two cloud-only Global Administrator accounts excluded from all Conditional Access policies, with long random passwords stored offline in a physical safe, alerting on any sign-in. Critically, they must not be PIM-eligible: an activation workflow that depends on the platform working is exactly what fails in the scenario you are defending against.

3. Design the logging and detection so privileged activity is retained for a year and the auditors' evidence is defensible.

Read the worked answer

Export immediately - native retention is far shorter than a year.

  • Retention reality. Entra ID sign-in logs are retained natively for 7 days on free tier and 30 days with P1/P2; audit logs are similarly short. A one-year requirement means diagnostic settings shipping SignInLogs, AuditLogs, and PIM activation events to a Log Analytics workspace, with interactive retention of 90 days plus long-term retention or archive for the balance. Do not assume the portal's date picker proves retention.
  • Azure activity logs for the subscription, plus resource diagnostic logs, to the same workspace.
  • Detections. Alert on: PIM activation outside business hours or by an unexpected account; any permanent role assignment created outside PIM; break-glass account sign-in; changes to Conditional Access or PIM settings; consent grants to new applications. These are the moves an attacker makes after taking an admin account.
  • Protect the evidence. Put the workspace in a dedicated subscription with a resource lock and restricted Contributor; an attacker with Contributor on the logging subscription can silence the alerts that would detect them.
  • Evidence quality: capture the activation justification and approval trail, not just the sign-in, because the auditors are asking who approved privileged use, not merely that someone authenticated.