itunes - ITunes won't automatically play next song

It depends what it does do when it gets to the end of the current song.

• If the same song plays again, then you have Repeat 1 turned on. Turn it off. (The Repeat button cycles through Off, Repeat, Repeat 1, and Off again.)
• If the player stops, that is probably because the tick boxes have all been turned off. You can see the tick boxes in the Songs View:

• If the tick boxes are all empty, hold down the CTRL key and click in any of the boxes. This will turn all the ticks in that list back on.
• If the tick boxes are not shown in your iTunes Library, click on Edit/Preferences/General, find the Show: List view tickboxes and put a tick in that box

The potential cause of this behaviour is if shuffle mode is enabled and all songs are marked as skip when shuffling.

tt2

Well spotted tt2.

You're welcome. 🙂

tt2

When did this start happening? Did you make any significant changes to your library just before this happened?