Troubleshooting Entra Cloud Sync in CIS-Hardened Environments: A gMSA Encryption Odyssey
When deploying Microsoft Entra Cloud Sync in highly secure environments, edge cases are expected in hardened environments, but this one unravelled in ways the docs didn’t prepare me for. But I recently hit a problem that took some carefully structured troubleshooting, lab testing, and plenty of false leads to fully resolve. The culprit? A seemingly innocuous group policy setting buried in CIS benchmarks. This post documents the full journey, from symptoms to root cause, and provides a resolution path for…