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Migrate Windows Server Essentials 2016 to Windows Server 2019

How to migrate Windows Server Essentials 2016 to Windows Server 2019 Standard, Datacenter or Essentials

The title of this guide suggests that it can only be used for migrating Essentials 2016 to 2019 but this is not true. You can use this guide also for migrating Windows Server 2016 Standard or Datacenter to the new Windows Server 2019 Standard or Datacenter.

Migrating Windows Server Essentials 2016 to Windows Server 2019 Essentials, Standard or Datacenter is a bit different compared to previous migrations where we came from any SBS version or Windows Server Essentials SKU before 2019 and migrated to any Windows Server Essentials version before 2019. 

The difference is that Windows Server 2019, either in Essentials, Standard or Datacenter version no longer includes the Essentials Experience role and that means we will have a different approach on migrating redirected folders, mapped drives and group policies. In this guide we migrate the following roles:

Role or data Is migrated in this tutorial
Active Directory Domain Services
Active Directory Certificate Services
Folders, folders and shares
Redirected folders (made by the Essentials Dashboard console/policies)
Security and/or permissions
Group Policies

Frequently Asked Questions

After you move FSMO roles to the new Windows Server Essentials 2019 SKU you are no longer compliant with the EULA. Microsoft enforces this by a 21 day countdown. After those 21 days are over your Windows Server Essentials 2016 SKU will shut itself down, it will be useless for you. You need to demote, unjoin and decommission the server and repurpose the hardware. If you migrated from Windows Server 2016 Standard + Essentials Experience role you can still use the server as a member server with the Essentials Experience role installed but this only valid if you are migrating to Windows Server 2019 Standard and NOT Windows Server Essentials 2019. The Windows Server Essentials 2019 SKU is limited to 25 users and 50 devices but it also only allows for one Domain Controller and it must own all FSMO roles.

If you migrated from Windows Server 2016 Essentials you have used Office 365 and/or Azure integration from within the Essentials Dashboard. That functionality is no longer included in Windows Server 2019 and no longer part of the OS. We will need to use Azure AD Connect sync: Understand and customize synchronization | Microsoft Docs

Technically you can but it is not supported. If you ask me I would never do that because it is something not supported by Microsoft and if you run into issues they will not support you and I will probably ask you if you have read this guide?

You should always virtualize, even if you only use Windows Server Essentials 2019 and you have only one workload. Migrating a virtualized workload is so much easier then physical.

At the bottom of this migration guide you will find a downloadable Zip file that contains the Powershell scripts to complete this migration. You need to unzip it to c:\scripts on each server. The scripts write output to a date and time stamped text file that can be used for troubleshooting or reporting.

This migration guide does not disrupt daily operations at all, so you do not lose any productivity time in your company. 

Clear and comprehensive technician guides so you can get it done

We excel at providing you the tutorials you need to get through that difficult project, migration or configuration. It's like having a virtual coach looking over your shoulder. The documentation you'll find here is priceless. Our technician guides have screenshots of every step and Powershell scripts if applicable. One on one support is included in the IT Pro and IT Pro Mentor subscriptions.

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About www.server-essentials.com 

www.server-essentials.com is founded by Mariette Knap, a Dutch Microsoft MVP. www.server-essentials.com is a community for IT Consultants and Business Owners who, themselves, take care of the IT infrastructure and Employees who do that little extra in the company to keep things running. Our forum is for discussing all things ‘IT’ and more.  Our documentation is top notch and written by and for the community.

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