I recommend to re-install the the vCenter server in the same directory without changing the directory location. Also, make sure to select “Do not overwrite, leave my existing database in place” option while the installation.
After successful re-installation of the server we checked the SSL certificate folder. It’s great to see that the new SSL certificate in place and last modified date is updated.
It is a green light to the next step and checked the vCenter server functionality by login to the vCenter using the vSphere client.
See my below output of the vCenter inventory. All the hosts were disconnected and below Warning was displayed in the summary tab.
This cased behind this is it was failed to Decrypt the root password since it was encrypted using the old SSL certificate. Once you are re-connecting the hosts you might see the below error message due to this password issue.
Ok, now it’s time to perform the actual 5.5 upgrade and mount the ISO to your vCenter and perform the upgrade. My installation method is simple installation, but I would suggest install each and every role one by one as a custom installation rather than perform the simple installation from the installation wizard.
Select the “Keep my existing database” in the Inventory Installation
Make sure to take a backup of your new SSL certificate before you proceed with the Upgrade.
I would recommend to select the “Automatic” as the vCenter Agent Upgrade method.
Wait until it performs the DB upgrade.
This is the way that I upgraded my very old vCenter server and I believe this will help you to find some answers for your questions.
Thank you for reading my post.