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.
Windows storage server 2008 r2 upgrade path.
I would choose the upgrade path outlined in your second sentence above.
As you are planning your upgrade be aware of the following guidelines for the middle step of upgrading to windows server 2012 r2.
Unfortunately i am pretty sure that there is no upgrade path directly from ws 2008 to ws 2016.
Insert the setup media for windows server 2012 r2 and start the setup exe.
Windows server 2008 r2 datacenter with sp1.
See upgrade paths for windows server 2008 for more information about your on premises upgrade options.
For on premises servers there is no direct upgrade path from windows server 2008 r2 to windows server 2016 or later.
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.
The following graphic shows the upgrade paths for windows server.
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.
Overview of windows server upgrades.
An in place upgrade allows you to go from an older operating system to a newer one.
As far as i know windows storage server 2008 is a oem manufacturer specific product and it is differente with windows server 2008 r2.
Upgrade windows server 2008 r2 to windows server 2012 r2.
3 minutes to read.
Upgrade windows server 2008 r2 to windows server 2012 r2.
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.
If your server is connected to the internet make sure you click on go online to install updates now recommended.
2 minutes to read.
This will download the latest updates to the installer.
Instead upgrade first to windows server 2012 r2 and then upgrade to windows server 2016.
Windows storage server 2012 standard.
Windows server 2012 r2 datacenter.
From my personal understand we are unable to upgrade windows storage server 2008 to windows server 2008 r2.
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 step by step guidance on upgrading review the windows server upgrade content.
For example windows server 2012 r2 and windows server 2016 can be upgraded in place to windows server 2019.
Hyper v server 2012 r2.
Cluster os rolling upgrade.