Due to an SSL issue, an upgrade from vCenter 5.5 Update 2b to 6.0.0 U2 failed. Using KB:2110943 I tried replacing the certificates but after much deliberation with VMware Support, they recommended I completely uninstall vCenter and re-install it to the latest version of 5.5 (Update 3e at the time of writing).
I followed the instructions from the KB:
- Reinstall the vCenter Server stack:
1. Uninstall vCenter Server in this order:
- vCenter Server
- vCenter Inventory Service
- vSphere Web Client
- vCenter Single Sign-On
2. Re-install vCenter Single Sign-On, vSphere Web Client, vCenter Inventory Service, and VMware VirtualCenter Server service.
3. Reconnect to the existing database.
4. Reconnect all of the hosts to the vCenter Server.
Rename the following directories under C:\ProgramData\VMware to ensure new certificates are generated using the correct hostname.
- CIS to CIS.old
- Infrastructure to Infrastructure.old
- SSL to SSL.old
- VMware VirtualCenter to VMware VirtualCenter.old
vSphere Web Client to vSphere Web Client.old
All the components installed current until it came to the VMware VirtualCenter Server service.
Setup located a vCenter Server database but not the companion SSL certificates. The SSL certificates should be located in the folder: C:\Program Data\VMware\VMware VirtualCenter\SSL\
Restore the SSL folder from the previous installation to the proper location before continuing or hosts will be disconnected and the vCenter upgrade will fail.
It appears that the installer had not created a C:\Program Data\VMware\VMware VirtualCenter\ and the subsequent SSL\ folder within To get past this issue we created the missing directory then the SSL folder under that. We then created blank rui.crt, rui.key and rui.pfx files in the SSL folder and pressed next on the installer. This magically got past error box! WARNING: Before pressing the next button go into the SSL directory and delete all the rui.*.* files you just created before proceeding.