Tutorials

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Migrate SBS 2008 to Windows Server 2016 Essentials

How to migrate SBS 2008 to Windows Server 2016 Essentials

Small Business Server 2008 has reached the end of life

Your old SBS server has reached the end of life already and it it is now the time to migrate. 

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

This migration guide will help you do that. Migrating from SBS 2008 to Windows Server 2016 Essentials or Standard with the Essentials Experience role installed is an easy job if you use our guides. This migration guide includes, very detailed, every step you should make to migrate your server. If you are not going to deploy the Essentials Experience role please use this guide How to migrate SBS 2008 to Windows Server 2016 Standard or Datacenter

Migrate Exchange Server 2007 mailboxes from the SBS 2008

Your Exchange Server 2007 mailboxes can be migrated to either Office 365 or an on-premise Exchange Server 2013 or 2016. A direct path from Exchange Server 2007 to Exchange Server 2016 is not possible, it is blocked by Microsoft. If the end result must be Exchange Server 2016 you must migrate first to Exchange Server 2013 and migrate that one to Exchange Server 2016. The guides are located here:

Easy to understand instructions and explanations

Every step in this tutorials 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. Our migration method does not disrupt daily operations at all so you do not lose any productivity time in your company.

Understand network layout

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
DNS
DHCP
Folders, folders, and shares
Redirected folders (made by the SBS console/policies)
Users
Security and/or permissions
Profiles
Exchange email to either Office 365 or a new on-premise Exchange Server 2016
Migrate printers

And at the end of the procedure, we will show you how you can safely remove the old server from your Active Directory. Our migration method does not disrupt daily operations at all, so you do not lose any productivity time in your company. And if you need to migrate Exchange email, like on an SBS 2008 we offer you several choices to migrate either to Office 365 or an on-premise Exchange Server in your network. 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.

Frequently Asked Questions

After you move FSMO roles to the new Windows Server Essentials 2016 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.

You can start with migrating your mailboxes from Exchange Server 2007 to Exchange Server 2013/2016 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 2016 + Exchange Server 2013.

It is possible to migrate Exchange Server 2007 to 2016 or 2019 but not without an extra hop. A direct migration path from 2007 to 2016 or 2019 is blocked by Microsoft. You need to migrate first to Exchange Server 2013. If all mailboxes and public folders are migrated to the Exchange Server 2013 you must uninstall Exchange Server 2007 from the SBS 2008. Without uninstalling Exchange Server 2007 you cannot install an Exchange Server 2016 or 2019. Once that has been completed you introduce an Exchange Server 2016 or 2019 and migrate mailboxes and public folders from the Exchange Server 2013.

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 2007 to a new Windows Server Essentials 2016 SKU or Windows Server 2016 Standard with or without the 'Essentials Experience' role and an on-premise Exchange Server 2013/2016/2019 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 on it but I prefer to virtualize that also. 

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 23. 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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