It’s been a while now since iOS 5 and the iPhone 4s were released, and I had yet to update my phone because of an array of puzzling issues that seemingly should not happen on an Apple product. First of all, even a simple backup was failing. This was most alarming because one, I was using a Mac Mini, an actual Apple desktop; and two, because I had never had an issue with iTunes on the Mac. This sort of process worked smoothly in the past, and I had no reason to believe the experience would be any different. Unfortunately, this was just the start of a bizarre string of events I encountered as I tried to straighten out the mess.

As you may have guessed, I am the typical ‘power user’. I use most of the space available on my iPhone 4, and only generally offload files when absolutely necessary. In this case, I deleted about 1GB of data from my phone before I started the process of backing up and upgrading the OS. Right off the bat, I was greeted by a message stating, ‘iTunes cannot sync apps to the iPhone because the apps installed on the iPhone could not be determined.’ What the…I had never seen this message before so I started Google-ing. It seems this is a pretty common problem, and most often it’s fixed by simply quitting iTunes and restarting it. Sure enough, that part was easy, and my apps were syncing as planned (or at least, so I thought).

Well, halfway through the sync, iTunes comes back and tells me the same thing. But just a second ago it was syncing fine. What kind of cryptic message is this? Either you can determine the apps or you can’t…you can’t start copying apps and then fail without offering up some additional information. This makes it really tough on the user – figuring out what to do next. At this point, rather than start trying every oddball thing I read in support forums, I decided to watch the sync process closely and try to find out which app was last to sync before crashing the routine. Normally, I’d just update all the apps I have but the app store denies that request, telling me the app requires iOS 5, so here I am, forced to update each app individually. As a power user, this means dozens of apps now that iOS 5 has been around for a few months. Anyway, the last app I saw appear during the sync process was Xfinity Moble, so I went to the app store and updated just that app. I then closed iTunes and restarted, and was greeted with a different message: iTunes found purchases on my phone that were not transferred to my library (really?). Sure, transfer those apps. Well, not so fast, actually.

After all that, the process is crashing again, with the same error, cannot determine apps. So what now? Am I stuck doing this with every application I have on my phone? This is going to take a while. Well, I fired off the the sync again and the next app to fail: Xfinity TV. Wait, what? It was just Xfinity Mobile that was giving me problems before. Now their TV app? Forget this – I am deleting this app and any app that gives me a sync problem from here on out. So I went ahead and deleted the app and here’s what I got: The iPhone cannot be synced because there is not enough free space to hold all of the selected items (additional 3.46 GB required). Whoa, seriously Apple? I am trying to backup my phone and you’re telling me to clear data off of it so I can copy something to it? This is absurd. Why would I clear data off of my phone in order to back it up? After looking a little more closely at the usage bar at the bottom of iTunes, apparently it determined that I have 5.8GB of ‘other’ files on my phone, leaving me 3.4GB over capacity. This is just simply not accurate, so I don’t know where the program would have determined this math.

After trying to close iTunes and restart it a couple times to get around this issue, I decided to go back to Google to find out if there was an easy fix. One of the first page results was a link to with an article recommending I turn off automatic syncing options. The one thing I felt I did not need to sync at this time was music, so I disabled that. It worked! Finally, I was able to sync the apps and get the backup process to complete. I only had to update an app, delete an app, and disable the music sync. What an aggravating mess.

One thing I did notice after this sync: I ended up with 250MB less storage space than when I started, and now I had no music on the phone. Apparently, when you deselect ‘sync music’ it disables all the music on your phone. I don’t recall seeing a message stating that this would happen if I unchecked that as part of the process. I expect the space freed up and the music deleted, so to see less free space than when I started the sync makes me feel even more uneasy.

In summary, I suppose it wasn’t as difficult a process to repair than other software glitches, but Apple could display more helpful error messages when iTunes fails. The lesson learned is: never underestimate the confusion a simple error message can cause.