For step by step guidance on upgrading review the windows server upgrade content.
Windows storage server 2008 r2 upgrade path.
I would choose the upgrade path outlined in your second sentence above.
Windows server 2008 r2 datacenter with sp1.
This will download the latest updates to the installer.
Also keep in mind that the cluster migration wizard can be used but is only supported up to two versions back.
An in place upgrade allows you to go from an older operating system to a newer one.
As you are planning your upgrade be aware of the following guidelines for the middle step of upgrading to windows server 2012 r2.
Hyper v server 2012 r2.
Cluster os rolling upgrade.
Unfortunately i am pretty sure that there is no upgrade path directly from ws 2008 to ws 2016.
See upgrade paths for windows server 2008 for more information about your on premises upgrade options.
The following graphic shows the upgrade paths for windows server.
2 minutes to read.
Windows server 2012 r2 datacenter.
For example windows server 2012 r2 and windows server 2016 can be upgraded in place to windows server 2019.
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.
Upgrade windows server 2008 r2 to windows server 2012 r2.
If you want to keep the same hardware and all the server roles you ve already set up without flattening the server you ll want to do an in place upgrade.
Cluster os rolling upgrade enables an administrator to upgrade the operating system of the cluster nodes from windows server 2012 r2 and windows server 2016 without stopping the hyper v or the scale out file server workloads.
Windows storage server 2012 standard.
Since you re respecting downgrade rights in the intermediate steps and ending at the licensed product i don t see that being a licensing issue.
For on premises servers there is no direct upgrade path from windows server 2008 r2 to windows server 2016 or later.
Instead upgrade first to windows server 2012 r2 and then upgrade to windows server 2016.
Overview of windows server upgrades.
From my personal understand we are unable to upgrade windows storage server 2008 to windows server 2008 r2.
If your server is connected to the internet make sure you click on go online to install updates now recommended.
The process of upgrading to a newer version of windows server can vary greatly depending on which operating system you are starting with and the pathway you take.
Even in supported upgrade paths from previous retail versions to windows server 2012 r2 certain server roles that are already installed might require additional preparation or actions for the role.
As far as i know windows storage server 2008 is a oem manufacturer specific product and it is differente with windows server 2008 r2.
In azure you ll stay compliant become more secure and add cloud.