Apple, My Shit Don't Sync

So, it wasn't that long ago that my Macbook Air was stolen. That device came from a longer line of devices that had served as sync point for my iPhones going back to my iPhone 3G. For nearly six years, my iPhone and my Macbook lived harmonious lives celebrating each other's existence. When the iPhone was plugged into the Macbook, the Macbook would recognize it, then say, "it's been a while since I've seen you. Look at all of the applications that I've downloaded for you. Here you go."

It was wonderful. A perfect family portrait. There were times when I even raved about the relationship -- like the time would I stood in line for nearly a day to get the iPhone 4, activated it, and was able to sync all my contacts in less time that it took them to prepare the Thai food I ordered for my return home. Prior to that moment, my experience changing phones was less than positive. My first phone call on that iPhone was to my girlfriend to let her know that my line ordeal was over and that I was going home. Yeah contacts. Yeah sync. Yeah iPhone. Yeah Apple. You made the phone switch a seamless experience.

Perhaps that set a basis for unrealistic expectations. When my Air was stolen, it turns out that many of my preconceived notions were taken as well. When I brought home a new Macbook, I expected it to connect to my iPhone and form the same kind of bond that my old computer had. After all, they are just electronic devices, right? When I first plugged my iPhone into the new computer, it gave me a warning, something along the lines of, "this iPhone is already synced to another computer, do you want to erase it and sync it to this one?"

The first time that I saw that alert, I still needed to move a bunch of data that -- at the time -- only lived on my phone. So I clicked cancel, not now, no, or whatever the "I don't really want to do that" option was. And from that point, things seemed to go well. I was able to move all of my photos and such off of the iPhone and onto the new Air.

For a day or two, everything seemed good. But then I started to notice a growing number of apps that needed updating. So I plugged my phone into the new Air and clicked okay on the erase and sync option. Mission accomplished -- or so I hoped.

Unfortunately, all that it seemed to do was blow out my playlists. I started out with an iPhone full of music and I ended up with an iPhone with no playlists on it. I had to go back into iTunes and redefine what playlists I wanted on the phone, then resync it. Annoying, but you tell yourself that this was probably a one time thing.

The other thing that I quickly realized was that my Apps didn't sync. I had apps to update, but they didn't update during the sync when I plugged the phone in. I tried unplugging then replugging the iPhone. I tried rebooting the iPhone. Still nothing. I dove down into iTunes to the Apps menu on the phone. Now I was presented with a list of the apps that were on the phone. Next to the apps that needed to be updated there was an update button. It looked like I needed to manually select update for the apps that I needed to update.

This was not the way that it used to work. And so I scoured the preferences and settings, looking for the thing that would fix this behavior. I looked on the iPhone and in iTunes. There is a setting for automatically sync apps, but that does it over the air. Not what I wanted. I thought that maybe the update to iOS 8 might fix all of that it didn't.

Finally, I was so frustrated, I made an appointment with the Genius guys at the Apple store. Side note -- a sucktastic feature of the Apple Store appointment engine, it doesn't create a calendar record or send you an email with the time for your appointment. I missed mine because I forgot which time I chose right after I closed the confirm window. I went back to look -- no record.

My Genius experience bordered on the worst ever. Since I missed my scheduled appointment, I was cycled through a serious of "not genius like technical genius, but smart guys" who didn't know much about iTunes and iPhone syncing to one last guy who changed the UI on my iTunes, complained about my use of the "original" trackpad scrolling direction, and checked all of the same settings that I had already looked at. His final proclamation -- after talking to someone else -- was that the behavior that I was seeing was the way it was supposed to work. That my previous version must have been an old version of iTunes. Now, according to this guy, all of the sync went from iPhone to laptop, not the other way around. And we were done.

Until a week or two later when the iOS 8.01 & 8.02 updates landed. My iPhone wouldn't update the apps and I wound up with a list of nearly 30 apps that needed to be updated. My theory is that it wouldn't update those apps until I updated the phone to the latest version of the OS. Eventually, I was able to go through and manually select update for all of the apps that needed updating, but it is so incredibly stupid that it makes me want to toss the phone across the room.

Today my iPhone shows a badge with 29 apps to be updated. I might as well have a carrier-designed Android phone it's so un-updated. But hey, this is the way that it's supposed to work, right?