One of the features added to the last update of iTunes is the ability to compress higher bit rate songs that are synced to your iPhone (and probably iPod as well, but I don’t have one anymore to test this) to save space and cram more of your music on your device. This makes a big difference for people like me that have very high quality audio tracks that take up a lot of space. So I jumped at the chance to take advantage of this feature. But I ran into a few problems. One is that there was one particular song that it couldn’t convert (I never could figure out why) and so it wouldn’t sync it, and it felt the need to notify me of this twice each time I synced my iPhone. The other is that all of a sudden my custom ringtones stopped syncing. The second part I attributed to a weird bug in the iTunes update and didn’t consider it a side-effect of the compression settings. And so I spent the next two weeks or so using only the standard ringtones (reminding me why I created the custom ones in the first place). A third problem is that iTunes didn’t sync the entirety of my playlists, there were several playlists that only contained half the songs they were supposed to, which really annoyed me.
Today I decided that I had had enough of the annoying compression-error pop-ups and not having half my songs with me, so I turned off the compression option and re-synced my iPhone. It took a little over an hour because it had to re-transfer all of my songs. Shortly after I finished syncing I received a call from a friend, and the iPhone played the custom ringtone I had set for him.
So my mysterious missing ringtones have been found, and I now know that this compression feature really needs some work because it just doesn’t work.