When Windows doesn't restart it is usually because there is a process in the background that has not finished. Get into Task manager (Ctrl-Alt-Del) and close some of the processes with a manual "End Task". Suggestion 1.) Sort the processes by double-clicking the Process Title. 2.) End Task only the Processes in CAPITAL LETTERS. These are usually not system processes and are started by other programs. 3.) Try 1st closing all CAPITAL processes initially (make sure to wait a full 3 minutes to make sure processes have cleared) then try and shutdown. 4.) If successful, next time try to pin down the exact process holding up the system by closing down a few at a time and waiting, then shuting down.
Last observation: if this happen when shelling in Linux -- then above may not help-- in such case then remember that every time you restart your computer, the virtual machine that runs in background will close, so you'll have to open VMware Server Console and start the Windows machine before you can connect to it through the desktop shortcut.
Let us know if you still continue to have issues. Best Regards
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