I'd like to start by stating that my iPod Touch 3G and iTunes worked fine before yesterday...then I upgraded to the latest version of iTunes and ios5. The Touch was previously jailbroken using redsn0w and DiskAid. This morning when I attempted to add music to my iPod, I had a problem. My usual routine for adding music is as follows: (1) Remove approximately 5 - 10 gb of music from my iPod and (2) start adding music 3 or 4 albums at a time from my music library (via drag and drop). During my routine this morning, I added my first selection of 6 albums (approximately 60 songs). By the time I was ready to add my second selection (another 50 songs), the first selection was only about half-way done uploading to the iPod. In the past, I would just drag and drop the second selection. iTunes would accumulate the both selections (60 + 50 = 110 songs), and continue from where progress left off (halfway through the first selection, or 31 of 110 files). However, after the updates, when I added the second selection, iTunes flashed "Preparing to Update" and started copying/transfering the second selection at the beginning (1 of 50), ignoring the second half of my first selection. I didn't notice that iTunes was doing this until about 20 minutes into updating my iPod. I looked at the music on my iPod, and it was filled with half albums. I have tried using different computers, restarting the computers, restarting the iPod, and restoring (recovery and DFU) the iPod. None of these have worked. I know it's a minor issue, but it's frustrating because managing music on the iPod for me is already a long, user-intensive process. This new issue makes the process almost undoable. Here are couple of other related problems: The capacity bar does not move while files are transferring from iTunes to the iPod Touch. The capacity bar only changes after the upload of the entire selection is complete. Another problem I noticed: when I add a selection (say 20 songs), iTunes shows "Preparing to Update," then it flashes "Copying file 1 of 28." It consistently adds approximately 8 more files than my selection. It adds the 20 songs in my selection, then flashes the last eight songs, which appear to be songs that are already on my iPod. I've searched for this problem relentlessly and have found nothing. I found one other person that had the same exact problem. Any help would be greatly appreciated.