Ran into the following error when working on the home lab: Failed to connect to VMware Lookup Service https://vcenter01.eeg3.lab:7444/lookupservice/sdk – SSL certificate verification failed.

SSL Verification Failed

It turns out this was caused by the SSL certificate still matching the original hostname, which the web client does not seem to like. Re-generating the SSL certificate is pretty simple, though:

  1. Log in the VCSA itself via https://<vcsa-name>:5480
  2. Navigate to the ‘Admin’ tab
  3. Turn ‘Certificate regeneration enabled‘ to ‘yes‘ by using the ‘Toggle certificate setting‘ button
  4.  Reboot the vCenter Server Appliance

During reboot, the following message should appear on the VM console: Regenerating the self-signed certificates.

Regenerating the SSL Certificates

Logging in through the Web Client should now work again. After the certificate was regenerated, I went back into the VCSA appliance and un-toggled the regeneration.

After doing the previous, I noticed regenerating the certificates can cause some oddities with other applications that depend on SSO, such as vSphere Data Protection:

VDP SSO Error

A reboot of the VDP appliance appears to be all that is needed to resolve the sync issue.