Upgrading Server 2008 R2 SP1 to a higher Server OS

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Upgrading Server 2008 R2 is now required to get to WS1 UEM 2008. This is necessary since the WS1 UEM 2005 version we are running on Server 2008 has a known bug with education classes and is fixed in WS1 UEM 2008 on-premise. Do you have any recommendations or guidance for things to watch out for when upgrading Server 2008 to server 2012 R2, server 2016 or server 2019 on an existing server? We have been a long time customer and are now trying to keep up to date. We are looking for some help from support and are not going to pay extra for that so submitted a ticket too (20159721209). We also attempted to install WS1 UEM 2008 on new server VM’s running server 2019 for Device Services and Console (Database server doesn’t need the OS upgrade) but because of the VM name changes (configured in internal and external DNS) devices were not communicating with the new VM’s so it was all rolled back to WS1 UEM 2005. We have heard it is not recommended to upgrade a server but it is the best option now for keeping things runnning correctly. Has anyone here done this successfully?

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