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I'm trying to configure vCenter to use SSL certificates that I generated with my Windows CA (Server 2008 R2).

I followed this to configure the cert template and issue the cert:

http://kb.vmware.com/selfservice/search.do?cmd=displayKC&docType=kc&docTypeID=DT_KB_1_1&externalId=2044696

And then used this utility (SSL Certificate Automation Tool 1.0) to update the certs: http://kb.vmware.com/selfservice/microsites/search.do?language=en_US&cmd=displayKC&externalId=2041600

However, after I update the certs (all successful messages) and reboot, my VMware VirtualCenter Server service fails to start. I'm curious to know if anyone has ever been successful with this or could point me to a better how to.

Also tried following this youtube video and update certs manually https://www.youtube.com/watch?v=MDV03H-gz6M but produced same result after reboot (again with no error messages during cert installs).

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Getting custom SSL certificates to work with vCenter is historically painful. 5.1 was the first version that VMware actually provided some guidance on the process (late in the version's lifecycle), but it was still pretty buggy. Derek Seaman has, in my opinion, one of the most comprehensive tutorials on getting things to work properly in his vCenter 5.1 Installation Guide series.

However, I'd highly recommend moving your vCenter to 5.5. There's no change in license requirement. The SSO service and web client are significantly improved. SSL certificates are still a pain, but less buggy. And you can still run your ESXi hypervisors on 5.1 if you have legacy reasons for doing so. Derek has a similar vCenter 5.5 series that includes a really nice PowerShell script for automating a lot of the SSL certificate provisioning.

And looking towards the future, vCenter 6 will supposedly have some sort of built-in SSL certificate management service to look forward to.

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