Q: You are supposed to be able to have thumbnail photos of your Contacts on the 5G iPod. I have photos added in Apple’s Mac OS X Address Book program, but they do not appear on the iPod, just white squares. Any ideas?
A: We’ve been having the same issue, and we’ve found a temporary and unreliable fix that may or may not work for you.
It seems that iTunes is stripping the image information from the vCard entries before it places them on the iPod. To circumvent this, open MacOS X’s Address Book, select the contacts you’d like to place on the iPod, and choose “Export.” This will create a single vCard file (complete with the picture information). To load this on your iPod, simply Enable Disk Use on your iPod, navigate to it’s “Contacts” folder, and place the newly-exported vCard file within that folder. You may need to delete old files named with iTunes or iSync in the file name.
This method worked for only a subset of our contacts that were supposed to have images. We believe that the feature was simply not reliable enough for public consumption by the time of the iPod’s initial launch, and so contact photos were removed entirely from the iTunes’ syncing process. We expect that the functionality will be restored in a future iPod Software Updater or iTunes update.
Update: Apparently this has been fixed in Apple’s latest update to MacOS X—version 10.4.3—which debuted on October 31st.