Failed to connect to VMware Lookup Service on VMware vCenter Virtual Appliance

I’ve been rebuilding my home VMware lab environment recently.  I decided to jump right into vSphere 5.1 with the vCenter Server Virtual Appliance instead of the traditional Windows SQL combo.  Deploying a vApp is much faster and cheaper from a licensing perspective than a full-blown Windows and SQL setup.  After I imported the vCenter Virtual Appliance .OVA,  I logged into the administrative web interface of the appliance (https://vcenterIP:5480) and started to make a few configuration changes.  First up were assigning a hostname, setting the correct time zone, and setting a static IP address.  The hostname change required a reboot of the virtual appliance.

After the reboot I tried to log into the vSphere Web Client at https://vcenterFQDN:9443/vsphere-client/.  The login failed with an error:

Failed to connect to VMware Lookup Service – https://vcenterIP:7444/lookupservice/sdk

The site showed an invalid certificate when it loaded.  When I viewed the certificate I found that the cert was issued to localhost.localdom.  This didn’t match my hostname and peaked my curiosity.

localhost.localdom certificate vmware vcenter virtual appliance

A quick google pointed me to this article: http://www.vi-tips.com/2012/09/vsphere-web-client-failed-to-connect-to.html. The confirmed that the invalid SSL certificate was the right place to start troubleshooting, but the resolution didn’t seem quite right. I poked around in the vCenter Virtual Appliance web admin interface.  On the Admin tab I found a button for ‘Toggle Certificate Setting‘.  This button corresponds with the ‘Certificate regeneration enabled’ option.

vcenter virtual appliance toggle certificate setting to fix Failed to connect to VMware Lookup Service error

After toggling this setting to Yes, I rebooted the virtual appliance using the reboot button on the System tab of the vCenter Virtual Appliance web admin interface.  After the reboot, I was able to log into the slick new vCenter Virtual Appliance vSphere Web Client.  The self-signed certificate now shows and Issued To: and an Issued By: name of the FQDN of my vCenter Server Virtual Appliance.

VMware vSphere 5.1 Web Client

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