After updating Encryption Management Server to a newer release that reboots the system automatically, VMware Tools services fail to start properly.
On reboot, if you press the Esc key on the keyboard to view the startup messages, you will see failures like this:
Encryption Management Server updates that include a new kernel will trigger an automatic reboot. If a new kernel is installed, VMware Tools must create a new initrd boot image for the kernel.
Encryption Management Server 3.3 and above running as a VMware Virtual Machine.
Create a new initrd boot image for the kernel by running the VMware Tools "configurator":