Why won't songs I downloaded from youtube transfer onto my iphone from iTunes?

I used an mp3 converter to download songs from youtube to itunes, and then download them to my iphone. I have done this with possibly close to 70 songs. But I just tried it with about 13 songs and it won't transfer, and it shows a little gray dashed circle next to the check mark on itunes, and it will play from itunes, but just won't transfer to my phone.

Are you using manual management of music and video? That's what you should be doing.

You might still have problems if you recently updated iTunes (wasn't there one last week) but haven't yet rebooted your computer. Also, sometimes you just need to exit and restart iTunes.

Hope this helps

  • Why won't songs from my iTunes transfer to my iPhone? I have already transferred over 350 songs. And i still have space left so it's not that. But certain songs won't transfer over and it's really annoying. Do you guys know why?
  • Why won't some songs transfer from my iPhone to iTunes on my computer? I've purchased many songs from iTunes on my phone and when I hook my phone up to my computer, most of them sync and are added to my library but some do not, which means when I go to the iTunes Store, it says I haven't purchased those songs when I actually have. Is there anyway to get them to sync onto the computer or should I try emailing Apple?
  • Why won't iTunes let me put certain songs onto my iPhone? ITunes used to work fine until recently. Now there are certain songs or artists that won't drag and drop onto my iPhone. Any answers?
  • Why won't iTunes let me drag individual songs onto my iPhone? I have the new itunes (11) and it won't let drag individual songs onto my iPhone. I tried looking it up on the internet, and one person said "make sure that your iPhone is setup to sync your songs manually instead of syncing only the checked songs/videos." What does that mean? I don't want all of my library on my iphone… Please Help!