Last updated: April 29, 2026
Most enterprise AD environments in 2026 are hybrid — on-premises AD synced with Microsoft Entra ID (formerly Azure AD) via Entra Connect. This gives users single-identity access to both M365 and on-prem resources. It also creates cross-cloud compromise paths that didn’t exist in pure on-prem AD. This module covers why hybrid AD attack surface is larger than the sum of its parts.
Why hybrid AD is risky
Two directory services, one identity. Entra Connect (formerly Azure AD Connect) synchronizes users, groups, passwords (hashed), and sometimes device objects. The sync creates trust relationships between on-prem and cloud that didn’t exist before.
Key paths:
- On-prem compromise → Entra Connect server → cloud identity compromise
- Cloud admin compromise → Azure AD Sync Service → on-prem AD write
- Password Hash Sync (PHS) puts on-prem NT hashes in the cloud
- Pass-Through Authentication (PTA) agents extend cloud auth to on-prem
- Seamless SSO uses a hardcoded AD computer account — attack vector
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