The company was running an on-premise Windows Server 2008 R2 as a VM under VMWare ESXi 5 hypervisor. Their existing server was performing active directory, File and Print Server functions using relevant server roles. Since Windows Server 2008R2 reached end of life, they wanted to upgrade to the latest Windows Server 2019 OS.
Solution
A successful and seamless migration of all VM’s from ESXI 5.0 to ESXI 7.0. Also, existing 2008R2 VM was replaced by latest Windows Server 2019 in a flawless manner by migration of all server roles, features & applications.
A temporary Windows Server 2019 Standard was brought to serve as an additional DC Server for an error-free migration from 2008R2 to 2019. The following procedures were carried out to ensure the seamless transition:
- Step 1 : A V2V Migration from the old VMWare ESX host to the new ESXi 7.0 host
- Step 2 : Migration of all the FSMO roles from the Windows Server 2008R2 to the temporary Windows server 2019 standard.
- Step 3 : Migration of all the FSMO role from temporary VM running windows server 2019 standard to a New VM running windows server 2019 Standard.
Once all the files were migrated successfully, the old Windows Server and the temporary setup were gracefully decommissioned. A postmigration support was also provided for the next few days.
Technical Challenges
There were two possible approaches to conduct this server migration, an in-place upgrade and Swing Migration. The in-place upgrade approach is more error prone since it requires a two-step upgrade to 2019 from 2008 and we have to take application & driver incompatibles in consideration. Hence a Swing Migration Approach was opted, for a seamless migration which is also the recommended approach by Microsoft.
Another one of the technical challenges that could have arose was that the users could have faced an Internet or a DNS Resolution Problem because of the transition of the Domain Controller. But because of the swing migration approach coupled with proactive planning, the risk was mitigated
Technologies Used

Accomplishment
- The migration was seamlessly carried out without hampering productivity of the staff.
- Successful migration of the other three VMs.
- The migration led to an enhanced performance and reliability.




