Another thing to check is if your iPod is compatible with the files you are downloading. The newer "Enhanced" audio format does not work on older iPods which will work with Format #4 and lower. They are not real clear on the what the "older" iPods are that doesn't support the enhanced format. My 5G iPod video will not sync enhanced format and must use format #4. I haven't tried to send the enhanced files to my 1G nano but they do sync to my other nanos as well as my 1G touch.