I am having the exact same problem. “Error while updating software: A certificate error occurred for the update server. Check your Internet settings or contact your system administrator.” I noticed that my VMware Player is using the update server:
https://softwareupdate.vmware.com/cds however when I go to that location directly in my web browser the directories are empty. I’m guessing this is where the problem is.
On the contrary, If I add a “ / ” to the end of the URL in my web browser:
https://softwareupdate.vmware.com/cds/ it brings me to what looks like the correct update server location which does not contain the empty directories as mentioned above.
Re-downloading the installer package from the website along with a complete uninstall and reinstall of the VMware player software has NOT fixed the problem on any of my machines.
Anyone else having this problem or know how to fix it?