10.8.3 iTunes issue?

[KyleBucket]

Hello everyone. My issue is something that's odd to type into a Google search and I haven't been finding what I've been looking for and I figured someone would be able to figure out a quick fix by just throwing it on here...

I had the highest version of Snow Leopard until the other day when I finally decided to get Mountain Lion. I'm all the way up to date, and until I switched to ML, I never had an issue - but, my iTunes checked songs don't play together anymore?

Example:
(Currently playing) Artist - Song title
(Checked box song underneath) Artist - Song title <--This song won't play, even though the blue box is checked?

As stated, this was never an issue before and I didn't change anything outside of the new OS...can anyone help me fix this issue?

Thank you!

 

[S.B.G]

Hello everyone. My issue is something that's odd to type into a Google search and I haven't been finding what I've been looking for and I figured someone would be able to figure out a quick fix by just throwing it on here...

I had the highest version of Snow Leopard until the other day when I finally decided to get Mountain Lion. I'm all the way up to date, and until I switched to ML, I never had an issue - but, my iTunes checked songs don't play together anymore?

Example:
(Currently playing) Artist - Song title
(Checked box song underneath) Artist - Song title <--This song won't play, even though the blue box is checked?

As stated, this was never an issue before and I didn't change anything outside of the new OS...can anyone help me fix this issue?

Thank you!

Can you post a screen shot of your example?

 

[KyleBucket]

Can you post a screen shot of your example?

For instance, "Doin It Right" will not play immediately after "Fragments of Time" is over. Before upgrading to ML, it did.

http://tinypic.com/r/28wcfg4/5

 

[S.B.G]

For instance, "Doin It Right" will not play immediately after "Fragments of Time" is over. Before upgrading to ML, it did.

http://tinypic.com/r/28wcfg4/5

What happens when you have the previous and/or current song checked?

 

[KyleBucket]

What happens when you have the previous and/or current song checked?

That actually fixed it. The following song played. However, that's a bummer because if it has to be songs in a row (all of a sudden?), I'll never have random "playlists." I liked being able to sporadically just pick some and it always worked with no issue.