iTunes not playing all songs in a playlist

Solution 1:

iTunes defines the random order of the tracks when you first specify set "Shuffle". (This is so that the skip forward / backward buttons work in a reasonable manner.) If you never turn Shuffle on or off, that order is never changed. Just disable and then re-enable Shuffle to get a new random order of tracks.

For more detail, see Why isn't iTunes shuffle random?.

Solution 2:

The only success I've had replicating this behavior is when I've unchecked some of the songs in a standard playlist. When I do this and play with shuffle turned on only the checked songs play. Perhaps this is your issue.

If you don't see any checkboxes on the left go to Preferences | General and check the box that says Show list checkboxes.

Solution 3:

Hey I have faced the same problem, and I did not get the correct answer. But after some hit n trail I got the solution:

Right Click on playlist from left panel >> select Add to Up Next option. Enjoy

Solution 4:

My solution to 'not playing all songs in a playlist (in my case, not doing continuous play one song after another; or in 'shuffle') was quick and embarrassingly easy - the shaded box in front of songs' titles did not have a check mark. Mystery as to how the check marks had disappeared?!? I did not notice this right off so I wasted time trying different things. So, I suggest step 1, make sure the boxes are checked.