Sticky please, as this is what I did and it fixed my problem.
This step by step will tell you exactly how to fix the problems of songs constantly resyncing or songs being on your zune but not registering on your software
1. Make sure no auto sync is set to on in the zune software.
2. go to
here and download the zune hd hack. (This is the download link I got from
here if the first link doesn't work go here to get the newest one.)
3. Install the patch, and then plug in your zune and turn on the zune program.
4. Go into my computer and select the zune (It will be under the name you gave your zune. It may also appear with two icons, click the one with the picture. If neither have a picture, just pick one)
5. Select portable, and than delete the song and the album cover directories.
6. Disconnect your zune, and than reconnect it. Have a pen and a piece of paper ready.
7. Write down all the songs/pictures/videos that are still syncing.
8. Go
here and download audacity to re-record your music. For video, upload the movie to youtube and than use
youtube downloader 3000 to download the .flv, than use a converter (such as
super C, which has a zune setting) to convert it back into a zune file. For pictures, either open it with a picture editing program and export it or find it on the internet.
9. Resync all your stuff back onto your zune. This should have cleared up all your taken up space and stopped the auto sync problem. If problems with the auto sync still occur, delete the files entirly.
Hope this helps.