Hi guys. I'm new to the Ipod/Iphone (have only had an iphone for a month now) and I had this problem also. However, I do work on computers and I do some programming so I went at this from a simple programming perspective. I had 169 songs, of which only 130 would transfer from my Itunes on my computer to my Iphone. What solved my problem was this: I went to Itunes on my computer and opened up my song list. There is a column to the right side of each song. In this column, some songs have a ! by them. If you will right click on that song, 70-236 then click "get info" it will take you to the folder where Itunes has stored your songs after you downloaded them. You need to link the song with where it is in the saved song list. For example, one of my songs I downloaded was "Baby Come Back". Itunes named this song's file name as Ambrosia - Baby Come Back. Actually Player sings this song, and I had renamed this file to read Player - Baby Come Back. 642-892 So I had to link this song from Itunes that read Baby Come Back and I had to link the location to the new name I had given to the song. That fixed every issue and now all of my songs are downloaded to my Iphone. I imagine this will fix whatever issue you have with songs not transferring. 642-524 If you right click on the songs with a ! to the left of them as they are listed in Itunes, then right click the song, then click "get info", and find the song manually, it will connect the song from Itunes to a legitimate place where the song is stored. You should only have to do it once per song.