Is it possible to upgrade the windows version of my DocuWare server?

It is indeed possible as long as the version of Windows is supported by your DocuWare system. This information can be found within the installation files of your current DocuWare version. As a precautionary measure, we suggest taking a backup of your DocuWare database before any changes are made. 
(Note: Operating Systems are considered external components and is not part of the standard support contract.)

KBA applicable for On-premise Organizations ONLY.