ITunes will only play one song. I have to hit play to start a new song. I have the shuffle on and I am in a playlist. I am running Windows 7. How do  I correct this to randomly play music, by itself?

iTunes will only play one song. I have to hit play to start a new song. I have the shuffle on and I am in a playlist. I am running Windows 7. How do I correct this to randomly play music, by itself?

That's consistent with all the tickboxes to the left of the tracks (in Song view) being unchecked.
Go into Song view and Ctrl-click one of the empty boxes to do a "global recheck".
If you can't see the tickboxes, head into your General preferences tab and select "Show list tickboxes" as per the following screenshot (it's for an earlier version of iTunes, but the boxes are in roughly the same place in the recent versions 11.x):

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