Is there a difference between doing a shutdown via Ubuntu's GUI versus doing a "sudo shutdown now" from the terminal? I ask this as I notice that my machines take longer to shutdown if I shutdown via the GUI.
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Did you mean sudo shutdown -h now
?
Anyways, as long as you use this ^^^ command, there should be no difference.
It probably takes longer to shut down from GUI since it has to kill the X server and such, whilst if shutting down from CLI they are already dead.

You'reAGitForNotUsingGit
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-h
is equivalent to--poweroff
, which is the default anyway. It's also likely that the OP is running from within the desktop environment, so X will still be running. – belacqua May 29 '16 at 00:05