From my personal understand we are unable to upgrade windows storage server 2008 to windows server 2008 r2.
Windows storage server 2008 r2 upgrade path.
If your server is connected to the internet make sure you click on go online to install updates now recommended.
For on premises servers there is no direct upgrade path from windows server 2008 r2 to windows server 2016 or later.
See upgrade paths for windows server 2008 for more information about your on premises upgrade options.
I would choose the upgrade path outlined in your second sentence above.
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.
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Also keep in mind that the cluster migration wizard can be used but is only supported up to two versions back.
Windows server 2008 r2 datacenter with sp1.
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.
Hyper v 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.
For step by step guidance on upgrading review the windows server upgrade content.
In azure you ll stay compliant become more secure and add cloud.
For example windows server 2012 r2 and windows server 2016 can be upgraded in place to windows server 2019.
Windows storage server 2012 standard.
Instead upgrade first to windows server 2012 r2 and then upgrade to windows server 2016.
Cluster os rolling upgrade.
Upgrade windows server 2008 r2 to windows server 2012 r2.
Insert the setup media for windows server 2012 r2 and start the setup exe.
An in place upgrade allows you to go from an older operating system to a newer one.
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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.
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.
Windows server 2012 r2 datacenter.
As you are planning your upgrade be aware of the following guidelines for the middle step of upgrading to windows server 2012 r2.
Overview of windows server upgrades.
Upgrade windows server 2008 r2 to windows server 2012 r2.
