I mean good grief! I simply want to copy a few songs from my iTunes to my iPhone, and I've spent 2 days of my life now on this, and I've not gotten anywhere with it! And I even have an iMac!! I've Googled the heck out of this problem, and in the end, Google responded with "Tough luck, buddy. You're on Apple devices, can't help ya!". I eventually concluded that I can't do it with iTunes. Why, because the songs on my (jailbroken) iPhone were originally put there from a different computer, and Apple doesn't like it when you do something crazy like try to put songs on your iPhone from different computers (error: "iPhone can only be synced with one library"). It especially doesn't like that my songs don't all come from the iTunes store (some came from my CD's, for example. But *none* of the songs I am trying to copy to the iPhone came from the iTunes store). Silly me, I thought I could keep the songs I had on my iPhone, then copy some songs from another computer. But nu-uh! Apple said "I'll erase your entire iPhone if you try that!". It eventually did succeed in erasing the songs that were on my iPhone, in the process of putting the new songs in. I tried the trick of copying the songs I want to transfer to a playlist, then using "Autofill" in iTunes to transfer the playlisted songs to my iPhone. It almost looked like that was going to work, when some of the songs transferred.... but then I learned it was too easy to be true. Some of the songs only had their *titles* transferred, and they now remain permanently greyed out on my iMac's iTunes. I can not even delete them from the iPhone in iTunes. Then I tried to find if there were any (free) 3rd party iPhone media transfer utilities for the Mac, that could do the job iTunes is supposed to. There are plenty for Windows, or for transferring from the iPhone to the Mac (which I do not need). But everything I tried for the Mac (freeware or not) that promised it could transfer songs to the iPhone did NOT work on Mountain Lion! Some tools were really crude and expect you to drop the music files into the iPhones raw filesystem (big no-no). The closest I came was using iTools to drag and drop the music files. It kinda sort worked, in that the files do show up on the iPhone (up until the letter "S"??)... but iTunes on the Mac shows those files no longer have their id3 tags! (And iTunes also still thinks the files that didn't finish copying from iTunes are still on the phone). I was pretty sure copying songs to the iPhone was possible. Is it actually not?! I'm still looking for a proper 3rd party iPhone music or media transfer program that will actually work properly with music files, and who's changes to the iPHone's playlist will be properly reflected once the device is loaded in the mac's iTunes. And that works on the Mac, on Mountain Lion!