I have tried retagging the albums with the artwork again, but it just won't transfer over.When I look at where the files are stored on my external hard drive, it seems like it is always the first song that doesn't show the artwork like the other songs do." Possible fixes Use i Tunes' built-in ability to fetch album artwork for your current i Tunes Library. In the i Tunes menu bar, click "Advanced," then "Get Album Artwork." Once i Tunes has retrieved the artwork, sync your i Phone or i Pod as usual.
Unfortunately, with the redesign of i Tunes 11, the long-established artwork pane in the bottom left corner disappeared, and with it one of the easier shortcuts for adding and removing album artwork.
Apple Support Discussions user imranus describes: "I am using an i Phone with 2.2 software.
My MP3s have album art pasted in the artwork space i Tunes provides or found by i Tunes itself or i Tunes store artwork.
You can also use third-party programs such as Cover Scout to help you find album artwork for your i Tunes music.
Mac Rumors forum user nomad01 tried the above without it resolving the issue, but came up with a solution that did work: "However, unticking the 'show album artwork on my i Pod' box, syncing the i Pod to remove all album artwork (quicker than it sounds), and then ticking this box and updating the i Pod again seems to have fixed it." Several other users confirm nomad01's suggestion as working for them.
Now look for where you saved the missing album artwork and click “Open”.