Why won't my music sync to my iPhone? - 1

I recently bought a new Macbook Pro, and I transferred all my songs to my iTunes. All my songs transferred perfectly fine; however, I obtain my music from other sources than iTunes (let's just say they are skillfully acquired). Whenever I download new music to my iTunes, it plays on my laptop, but it will not sync to my iTunes. If anyone knows a way for me to transfer these skillfully acquired songs, I would greatly appreciate it!

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  • Why won't my music sync to my iphone? - 3 Ok well i'm trying to Sync my tones to my Iphone 4 but its not letting me, when i click on sync on Itunes it says "Preparing to Sync" then "Determining apps to sync" then it stops, it doesn't sync it. What can i do?
  • Why won't my music sync to my iphone 4? Everytime I try to sync it, it just says the apps can't be determined! I'm only trying to sync one playlist!
  • Why won't my music sync to my iphone 4S? I just restored my iphone 4S and everything synced perfectly fine, contacts, mail, apps, everything except music. I tried re-syncing, making sure I had checked each song in my music library, checked "sync music" on my phone settings on itunes, manually checking the music I want under "selected playlists" and what not. I have absolutely no idea what to do now.
  • Why won't my music sync to my iPhone? - 2 I have an iPhone 3g. It's never had a problem before this. I hit sync because I just got a lot of new music, and when I checked to see if it was there, it wasn't. I even restored the device and now even LESS music is on there. The "manually move it" or whatever isn't checked. It's not corrupted. Maybe the music files?