For a few weeks I noticed that certain podcasts wouldn't sync to my iPod Nano. I searched on web forums and apple support without finding any answers. I would drag a selection of mp3 tunes from the iTunes main window to the Nano within iTunes, and only some of the songs would transfer. I would never buy any DRM'd music from Apple so the problem has nothing to do with authorization.
So then I looked closely at the filenames. The files that didn't transfer had "funny" characters like "?", "_", "'" (single quote) and "!". After renaming these file in iTunes, I had the nice feeling of seeing the Nano accept the files.
Now this is with the latest firmware for the Nano and iTunes software (7.6 (29)) as of Friday Feb. 8, 2008.
I saw many sad people posting about this problem on forums across the web. And the Apple troubleshooting page had the usual "reboot, reset, restart" crap. Which didn't work. I can't believe something this simple isn't generally known?
So I hope people find this. Let me help:
"Nano won't sync certain songs."
"iPod won't sync certain songs."
"Help please: some songs won't sync to my Nano."
