** Please note that this blog post assumes that you have already reviewed and utilized the "Using VMWare Infrastructure 3 with Dynamic Desktop Controller" found at http://support.citrix.com/article/CTX116928 **

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Recently, while at a customer during a XenDesktop 3.0 configuration we found that communication to VirtualCenter's SDK via https would not complete it's handshake.  Further research found that the Self Signed Certificate that the VIC/VC uses is created at the time of the Virtual Center install.  During the VirtualCenter install, the self signed certificate is created for a term of 3 years.  In this case, the certificate for this VirtualCenter had expired on 3/30/2009.  If you are attempting to connect with the XenDesktop Setup Wizard, or your XenDesktop DDC is attempting to communicate with VC and you receive a "SSL Handshake Failed" please check your certificate.

The certificate can be found at c:\Documents and Settings\All Users\Application Data\VMWare\VMware VirtualCenter\SSL.  You will find three files in this directory, rui.crt, rui.key, rui.pfx.  Double click on rui.crt to establish whether the certificate had indeed expired.  The VMWare document on how to resolve this issue can be found at: 

http://www.vmware.com/pdf/vi_vcserver_certificates.pdf

The Readers Digest Condensed version is to run a Repair on your VirtualCenter which will create a new self signed certificate for three years.  You should now be able to communicate into the VirtualCenter with XenDesktop as need be.

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Special thanks should goto Stephen Odanga of FCB for assisting me with finding this information.