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Domain Migration: Windows 2008R2 to Windows 2019 – Challenges & Mitigation

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Scenario: Our RED.COM domain initially built on Windows Server 2003. A few years back, it was migrated to Windows Server 2008R2. Presently two DCs - both are Windows Server 2008 R2. The Domain Functional Level & Forest Functional Level is Windows Server 2003. We have planned to introduce Windows Server 2019 DC in this infra & coming days Windows 2019 DC replace the Windows 2008R2 DCs.                 Trivia¹ : Prior Windows 2008, replication has happened through FRS (File Replication Service). From Windows 2008 it becomes DFSR (Distributed File System Replication) where instead of whole, it replicates only the delta of change. Migration Challenges: 1.        Windows Server 2003 Domain & Forest Functional Level does not support Windows 2019 DC. So DFL & FFL must be raise. Here we’ll raise both functional level to Windows Server 2008R2.    2.      Windows 2019 DC does not support FRS (File Replication Service) SYSVOL replication, it m