I have tried numerous times to recreate the keypairs, but it seems that after the first time, if I tried again, it seems to take forever, not sure if you want to call this a bug or what. I found out if I restarted my server, then it goes back through recreating a new set of keypairs, it takes maybe 5 minutes. So, to me it seems as if there is a problem with it running in memory for a long time, this is going through Kleopatra. If I do this through cmd line then is goes much faster. Or maybe you could shed some light as to why it does this, thank you.
Please explain what you mean by "recreate the keypairs". What do you mean by "server" - are you using gpg4win on a headless Windows installation?
The OS runs Windows 2008 R2 , on a Oracle's Virtualbox, so I wouldn't consider this being a headless Windows installation, why? When you first create your keypairs it goes pretty fast usually under 5 mins. But if you recreate or try an create a new keypair it never completes, takes 20+ minutes or longer. But if you shut down the OS, or restart the OS, and try it again then it completes in under 5 mins.
Can you try to kill the gpg-agent process from the task manager before you create the second keypair? If that helps the problem might be the same as T3378. Are you creating a standard key (ie. rsa2048) or something else?
Priority Low as it's partly a question and We can't reproduce (for me keygen is reasonably fast)