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Migrate SBS 2008 to Windows Server 2016 Standard or Datacenter

How to migrate SBS 2008 to Windows Server 2016 Standard or Datacenter

Small Business Server 2008 has reached the end of life

SBS 2008 support is expired so we need to migrate to a newer OS like Windows Server 2016. This migration guide will help you do that. Migrating from SBS 2008 to Windows Server 2016 Standard or Datacenter is an easy job if you use our guides. This migration guide includes, very detailed, every step you should make to migrate your server. 

SBS 2008 OS Version Begin mainstream End of Mainstream End of Extended
Windows Server 2008 SP2 4/29/2009 1/12/2015 1/14/2020
Exchange Server 2007 SP3 6/7/2011 4/10/2012 4/11/2017
SQL Server 2005 SP4 12/13/2010 4/12/2011 4/12/2016
SQL Server 2008 SP4 7/7/2014 7/8/2014 7/9/2019
Microsoft Windows SharePoint Services 3.0 Service Pack 3 10/24/2011 10/9/2012 10/10/2017
Source Search product lifecycle

Should I use this guide if I want to install the Essentials Experience role?

This guide does NOT install or use the Essentials Experience role, we choose plain Windows Server 2016 Standard or Datacenter. This means we will have a different approach to the migration of the Redirected Folders and the use of the SBS 2008 Group Policies involved. This is very well explained in chapter 12 and 13. In addition to this, we have developed some Powershell scripts that now uninstall silently the SBS 2008 ClientAgents from your workstations and laptops without actually touching the desktops. Very cool! 

If you want to implement the Essentials Experience role in a migration scenario from SBS 2008 to Windows Server 2016 please use this guide Migrate Small Business Server 2008 to Windows Server 2016 Essentials

Migrate Exchange Server 2007 mailboxes

Your Exchange Server 2007 mailboxes can be migrated to a new Exchange Server 2016 running on Windows Server 2016 or you can migrate to Office 365. The guides for those migrations are located here:

Remember that migrating to Exchange Server 2019 is not possible from Exchange Server 2007. We need to migrate first to Exchange Server 2016 AND we must get the SBS 2008 out of the way and raise the functional level of our Domain Controllers to a minimum of Windows Server 2012 R2. Exchange Server 2019 can ONLY be installed on Windows Server 2019 and higher. More reading Exchange Server 2019 system requirements, Exchange 2019 Requirements, Exchange 2019 Memory Requirements, Exchange 2019 Client Compatibility | Microsoft Docs

Easy to understand instructions and explanations

This tutorial describes in depth the correct method to migrate an old SBS 2008 to a new Windows Server 2016 Standard or Datacenter.

Sample network layout in a typical SBS 2008 network during a migration

Every step in this tutorial has a screenshot and if any Powershell is involved we have made it easy for you to copy it to your own situation. This tutorial will guide you from the start until everything has been migrated to the new server. Users, security groups, files, folders, shares, and permissions are migrated so there is no loss of data or do you need to recreate profiles or users. And at the end of the procedure, we will show you how you can safely remove the old SBS from your Active Directory. 

A complete migration guide for your SBS 2008

In this migration tutorial, we migrate everything, and that includes the Domain Controller, AD, DNS, DHCP, files, folders, users, security groups, shares, and permissions, so there is no loss of data or do you need to recreate profiles or users.

Role or data Is migrated in this tutorial
Active Directory Domain Services
Folders, folders and shares
Redirected folders (made by the SBS console/policies)
Security and/or permissions
Exchange email to either Office 365 or a new on-premise Exchange Server 2016
Migrate printers

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

Frequently Asked Questions

After you move FSMO roles to the new Windows Server 2016 Standard or Datacenter you are no longer compliant with the EULA. Microsoft enforces this by a 21 day countdown. After those 21 days are over your SBS 2008 will shut itself down, it will be useless for you. You need to demote, unjoin and decommission the server and repurpose the hardware.

No, a direct path from the version of the Certification Authority in SBS 2008 to the version in Windows Server 2016 is not possible. Because of this we do not migrate the CA in this guide but for most SMB's this is not an issue because they don't use it. If you need to migrate the CA to Windows Server 2016 you first need to migrate to a CA installed on a Windows Server 2012 R2 DC, backup the CA and restore to a Windows Server 2016 CA.

Yes, but you need to do that in multiple steps. A direct path from Exchange Server 2007 to 2016 is blocked by Microsoft. You need to migrate first to Exchange Server 2010 or 2013 (Migrate Exchange Server 2007 from SBS 2008 to a new Exchange Server 2013 on Windows Server 2012 R2), remove the old Exchange Server 2007 from the SBS 2008 and then migrate to Exchange Server 2016 (Migrate Exchange Server 2013 to Exchange Server 2016 in a SBS migration scenario

You can start with migrating your mailboxes from Exchange Server 2007 to Exchange Server 2010/2016 even before you migrate the FSMO roles or do any other of the migration-related procedures in this guide but I urge you to complete chapter 1, 2, 3, 4 and 5 before introducing the new Windows Server + Exchange Server.

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?

A migration from SBS 2008 to a new Windows Server 2019 Standard or Datacenter and an on-premise Exchange Server 2016 server is a total of two workloads. We do not purchase two physical servers for that but we virtualize. This means we install one Hyper-V host and two Virtual Machines. If you migrate email to Office 365 you will have one server on-premise and in that case, you can purchase one server and install Windows Server 2016 Standard or Datacenter on it but I prefer to virtualize that also. It makes migrating in the future much easier.

With this migration tutorial, you don't need anything else! For an overview of all migration tutorials visit Migration guides for Windows Server 2012 or 2016 Essentials.

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.

The most asked question is when do you migrate Exchange Server 2007 mailboxes. There is no easy answer to that question. It can be before you start the migration of the rest (this guide) or you can do it during this migration but before chapter 21. One thing you should understand is that uninstalling Exchange Server 2007 from the SBS 2008 kills the SBS 2008 Dashboard and Remote Web Access. There are tricks to get Remote Web Access working again, but you can no longer use the SBS 2008 Dashboard, it is crippled. If you are not sure what to do, please open a ticket at Premier Support for SMB, and we will help you.

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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