Windows Server 2008 and 2008 R2 documentation Migration assistance with the Azure Migration Center The Azure Migration Center has a full range of tools available to help you assess your current on-premises environment, migrate your workloads onto Azure,. By migrating SQL Server to Azure Managed Instances or VMs, you get three more years of Windows Server 2008 R2 or 2008 critical security updates, included at no additional charge. Leverage existing SQL Server and Windows Server licenses for cloud savings unique to Azure.
-->- Windows Server 2008 and Windows Server 2008 R2 are approaching the end of their support lifecycle.This means that as of the dates in the table below there will be no additional.
- On January 14, 2020, support for Windows Server 2008 and 2008 R2 will end. That means the end of regular security updates. Don't let your infrastructure and applications go unprotected. We're here to help you migrate to current versions for greater security, performance and innovation. On January 14.
- Windows Server 2008 R2, Windows 7, Windows Server 2008 and Windows Vista: Limited by available kernel-mode virtual address space. Starting with Windows Vista with Service Pack 1 (SP1), the paged pool can also be limited by the PagedPoolLimit registry key value.
Extended support for Windows Server 2008 and Windows Server 2008 R2 is ending on January 14, 2020. There are two modernization paths available: On-premises upgrade, or migration by rehosting in Azure. If you rehost in Azure, you can migrate your existing Server images free of charge.
![Server Server](/uploads/1/2/4/8/124897577/460393938.jpg)
On-premises upgrade
If you need to keep your servers on-premises, and you are running Windows Server 2008 or Windows Server 2008 R2, you will need to upgrade to Windows Server 2012/2012 R2 before you can upgrade to Windows Server 2016. As you upgrade, you still have the option to migrate to Azure by rehosting.
See Upgrading from Windows Server 2008 R2 or Windows Server 2008, for more information about your on-premises upgrade options.
If you are running Windows Server 2003, you will need to upgrade to Windows Server 2008. See upgrade paths for Windows Server 2008 for more information about your on-premises upgrade options.
Migrate to Azure
You can migrate your on-premises Windows Server 2008 and Windows Server 2008 R2 servers to Azure, where you can continue to run them on virtual machines. In Azure you'll stay compliant, become more secure, and add cloud innovation to your work. The benefits of migrating to Azure include:
- Security updates in Azure.
- Get three more years of Windows Server 2008 R2 or 2008 critical and important security updates, included at no additional charge.
- No-charge upgrades in Azure.
- Adopt more cloud services as you are ready.
- By migrating SQL Server to Azure Managed Instances or VMs, you get three more years of Windows Server 2008 R2 or 2008 critical security updates, included at no additional charge.
- Leverage existing SQL Server and Windows Server licenses for cloud savings unique to Azure.
To get started migrating, see Upload a Windows Server 2008/2008 R2 specialized image to Azure.
To help you understand how to analyze existing IT resources, assess what you have, and identify the benefits of moving specific services and applications to the cloud or keeping workloads on-premises and upgrading to the latest version of Windows Server, see Migration Guide for Windows Server.
Upgrade SQL Server 2008/2008 R2 in parallel with your Windows Servers
If you are running SQL Server 2008/2008 R2, you can upgrade to SQL Server 2016 or 2017.
Additional resources
Active11 months ago
Our goal is to upgrade a machine from Windows Server (WS) 2008 R2 to WS 2016. For now, we don't want to perform a clean-install to the server OS.
But according to Microsoft documentation, there is no direct path to upgrade from WS 2008 R2 to WS 2016 but we can upgrade from WS 2008 R2 to WS 2012 R2, and then to WS 2016.
Since we are not going to use WS 2012 R2 at all, I was wondering if I can use evaluation versions of WS 2012 R2 and WS 2016 to sequentially upgrade from WS 2008 R2 to 2016, and then buy retail version (of WS 2016) to convert the WS 2016 evaluation to a retail version. Is this possible?
Humberto Castellon73611 gold badge33 silver badges1616 bronze badges
Tae-Sung ShinTae-Sung Shin
2 Answers
![Download Download](/uploads/1/2/4/8/124897577/465844849.jpg)
It is always possible to update evaluation version to retail using DISM cmdlet. According to the Microsoft document - https://docs.microsoft.com/en-us/windows-server/get-started/installation-and-upgrade
Windows Server
'You can upgrade from an evaluation version of the operating system to a retail version, from an older retail version to a newer version, or, in some cases, from a volume-licensed edition of the operating system to an ordinary retail edition.'
Also, you can check Server Role upgrade matrix here: https://docs.microsoft.com/en-us/windows-server/get-started/server-role-upgradeability-table
batistuta09batistuta09
I once used retail versions to upgrade a
2008 R2
to 2012 R2
and then to 2016
, that works. But I don't think you can use an evaluation version to upgrade a retail version at all. But you may not have to activate the 2012 R2
before moving on to 2016
, so any 2012 R2
retail DVD may help.This reason why you may want to upgrade rather than do a clean install, is that you have complicated third party software on the server that is very difficult or impossible to install on a clean OS.
Peter HahndorfPeter HahndorfWindows Server 2008 R2 Disk Cleanup
11k33 gold badges3131 silver badges5353 bronze badges