Certificates and VMware don’t go together like a horse and carriage… And while I’ve never really had a major issue with SSL certs in VMware mainly because on a personal level I am ok with using self signed or default certificates (queue security nuts) I was forced recently to change a publicly signed vCenter SSL Certificate which also doubled as the Web Client SSL Certificate. This was due to VeriSign revoking the certificate that had been purchased on a per year renewal plan…the vCenter Client doesn’t like revoked certs.


Prior to vSphere 5.5 my usual trick of simply replacing the rui.crt and rui.key files in the vCenter/Web Client SSL folder and restarting vCenter didn’t work…in fact the vCenter Service (5.5 Update 2) won’t start if its done that way anymore…this is mainly due to the reliance on the SSO and Inventory services that don’t like the SSL thumbprint to be changed underneath them.

To resolve this I had to read through and learn how to use the VMware SSL Certificate Automation Tool. Once mastered it’s a great tool and lets you change/update all relevant vSphere SSL Certificates. Below is the quick and easy command line walkthrough to get the job done…note that you need to build up the SSL Certificate Chain correctly and make one small modification the ssl-environment.bat file

set ssl_tool_no_cert_san_check=1

A Couple of vCenter and Web Client service restarts later and the SSL Certificate has been replaced. While there are a lot more options there I only needed two steps to replace the original publicly signed certificate as all other certificates where the internally generated certs…As a specific heads up from the KB, these where the issues I ran into

  • SSL Certificate Update fails if vCenter Single Sign-On Password contains spaces or special characters such as &, ^, %, <.If the vCenter Single Sign-On password has a space or any special characters, such as &, ^, %, or <, the configuration of the Inventory service fails.To work around this issue, change the vCenter Single Sign-On password so it does not contain a space or any of the special characters &, ^, %, < in it.

  • If the certificate chain file for vCenter Single Sign-On is out-of-order, you see an error similar to:Certificate chain is incomplete: the root authority certificate is not present and could not be detected automatically. The presence of the root certificate is required so the other service can establish trust to this service. Try adding the authority certificate manually.To resolve this issue, ensure that the certificate chain file for vCenter Single Sign-On is created in the correct order. For more information, see Generating certificates for use with the VMware SSL Certificate Automation Tool (2044696).