Issue:
1. Select Restart.
2. Dock disappears along with all icons. However, background stays on the screen and the Mac never restarts.
Solution:
Option A:
You can hold down power button for two seconds. This works but is not a good way especially if you also need to install updates.
Option B:
1. Issue a Restart
2. When Finder goes away and you are stuck, do a Apple Shift Escape to bring up the Force Quit dialog. Relaunch Finder.
3. Start Activity Monitor.
4. Show "All Processes" in upper right, if not already selected.
5. Kill the stuck activity.
In our case we had to kill the VMware Fusion vmnet services and the WindowsServer services.
Killing the WindowsServer service had the immediate effect of killing Finder and all GUI. A prompt displayed saying there were updates and did we want to install. After that, the Mac installed the updates and restarted. Since then the Restart option is working again.
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