This might be a multipart question as it effects my vsphere and esxi hosts. I have a setup which works just fine but i am running into issues with the SSL Certs of vcenter or ESXI hosts when i try to use the upload otion to upload new images to datastore. I also get warnings when connecting to my vsphere or esxi host that cert dont match as i use name and the cert is for ip. So what i want to do is replace only the SSL cert which deals with the web interface on vsphere and on all my esxi host, create a csr, then get it signed by a CA authority and import the new host.cer. For some reason this seems to be more complex then it needs to be. In a normal hosting enviorment i can just use openssl , create a key, create a csr, get it signed and import it but that would be to easy.