Windows Server 2008 End of Support – Migrating File Servers

With the End of Support for Windows Server 2008 on January 14th, 2020 – you no longer have the ability to receive Security Updates or Support for any servers running Windows Server 2008. If you need to keep these systems under some level of support after January 14th – you have a few limited options:

1) You can migrate your Server and workload up to Azure ( and receive up to 3 free years of Security Updates and Support from Microsoft.
2) Provided you have an Enterprise Agreement / Volume License Agreement or you have purchased Software Assurance – you can enter into an Extended Support Agreement with Microsoft for up to 3 years and you will be able to register / enroll a fixed number of systems into this program.

Lets be honest – neither of these is a good LONG TERM strategy. Ultimately you need to migrate your workloads OFF of the old platform and on to a NEW platform (like Windows Server 2019). How do you go about doing that for key WORKLOADS that can’t migrate up to the Cloud? I tracked down Ned Pyle, Principal Program Manager from the Windows Server Team to talk shop about the #1 Workload for servers: “The File Server”.

Ned walks you through the functionality of his Storage Migration Service (free with Windows Server 2019) and the 3 phases of it’s operation: Inventory / Transfer / Cutover.

source by IT Ops Talk

windows server dhcp


Léa LOPEZ, Telecom System Administrator, Ambala College of Engineering and Applied Research, Ambala (INDIA)

4 thoughts on “Windows Server 2008 End of Support – Migrating File Servers

  • May 27, 2021 at 11:46 am

    Thanks for this Ned. to bite the bullet. You don't say if the servers being migrated have to be down during the migration? Can we simulate the migration as in do a test migration, then if all looks good then hit the file live button?

  • May 27, 2021 at 11:46 am

    Hi, I noticed we have moved on-prem file server to Azure sever, can we not move file share from Windows 2008 straight to Azure File share (Azure Storage Account)?


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