We recently encountered a new problem syncing with iTunes after updating an iPhone to OS 3.0. After updating, the iPhone began to sync properly, then stalled, ending in "error 13019."
We researched the issue and found an Apple support document with details about error 13019 and two possible solutions. The document explains that the problem is usually caused by syncing music and recommends that you remove all music syncing, sync your iPhone, then add music back and sync one last time. If you're lucky, this step may fix the problem. We weren't so lucky, however, and found ourselves hunting for other iPhone media--apps, voice memos, ringtones, podcasts, movies, TV shows, audiobooks--that might have caused the problem.
Troubleshooting this issue is tedious and involves going to each media type (listed above), unchecking it in iTunes, syncing to remove the media, then adding back the media by checking it in iTunes, and finally syncing again. Eventually, you'll find the media type that is causing the problem. Apple recommends then leaving that media type unchecked to prevent it from syncing with your iPhone--not a thrilling solution.
Users discovered that voice memo syncing, specifically, causes error 13019 and it occurs whenever voice memos are selected in the Sync Music panel by selecting Include voice memos in iTunes (see photo above). If you uncheck them, your iPhone will likely sync normally. However, we ended up deleting our voice memos from our iPhone before it would sync without errors again. Once we did this, iTunes syncing no longer produced the 13019 error.
Due to this bug, we don't recommend using the Voice Memo app on your iPhone or syncing voice memos in iTunes until Apple fixes the problem. If you absolutely have to use the app, consider turning off voice memo syncing in iTunes first.
Are you experiencing any other problems with iPhone OS 3.0? Tell us about it in the comments or write to us at firstname.lastname@example.org