Hello,
we would suggest to update your PRTG 7 version to 8, then backup and move your PRTG 8 installation as described here (if you want to buildt your Win2008 new from scratch on your old machine):
https://www.paessler.com/knowledgebase/en/topic/413-how-can-i-move-my-prtg-installation-to-another-computer
You should now have a PRTG with your existing config and data on the new Windows 2008 machine. Check if all sensors are running because sometimes there are some WMI issues depending on different Windows versions.
Then setup Win2008 on your old machine.
After both of your machines runs with Win2008 switch on the cluster mode on your PRTG on the new machine. This will be the ClusterMaster.
Install now PRTGv8 on the old machine and select install as a cluster member. This will be your ClusterFailover.
If you want to upgrade your Win2003 without setting up a complete new Win2008 you could skip the move PRTG part (but make a backup of your PRTG anyways). Just make sure that the PRTG installation with all your existing data and settings will become the ClusterMaster, because the master will distribute the settings to the failovers.
How to make a backup of PRTG:
https://www.paessler.com/knowledgebase/en/topic/523-how-do-i-backup-all-data-and-configuration-of-my-prtg-installation
kind regards
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