When I got my first iPhone a few years back my only computer was what is now a dying MacBook Pro. At the time I happily set my iPhone up using the laptop, and had the device sync to iTunes authorizing that computer to transfer files from the phone to the Mac. At the time life was good but not perfect. iTunes pretty much sucked then as it does now. And the whole syncing devices for your music and apps was, and is pure BS. That laptop is now on its last legs and I decided to go ahead and try to movie the iPhone to the iMac I bought about a year ago. The process has been a nightmare, and I can’t believe this software is owned and distributed by Apple.
Last night when I plugged my phone in, I got the standard message “This device is synced to another iTunes Library”, the rest of the message basically says if you proceed I’m going to wipe the device of all things not associated with this iTunes Library. I don’t get it, why the hell doesn’t iTunes look at your “Account” and not some computer specific library? If I log into iTunes, it should see that I am the authorized owner of the account, the iPhone, and the iMac and say OK lets back up the phone, and update the iPhone software. It shouldn’t erase anything.
After digging around I found that there is this new feature under the File menu that lets you “Transfer Purchases from you iPhone”. OK that seemed simple enough, but when I went to do that, I got repeated requests to enter my iTunes password for things being transferred. What sucked was it was asking me to authorize my iTunes accounts, for email addresses that haven’t been attached to my account for years. I was asked to provide a password for an email account that I used 8 years ago when I first used the iTunes store. It’s been so long, I couldn’t tell you that password if my life depended on it, so I was forced to use the password reset feature for the account. This happened two more times. I’m not sure what is going on here, but iTunes is obviously linking to some embedded meta data in a hidden file somewhere, and isn’t smart enough to look at the account I’m logged in under, cross check the data, and say “Hey, Same Name, Same Address, Same Billing Info, Same Credit Card Info, Same File and Song Names…” You would think that by the time Apple got to version 10 of this piece o junk software, they would have eliminated all the hardware BS and would be using the cloud to manage your account.
When I looked at some of the chat threads online, I noticed a consistent theme. De-authorize all your computers, Sync your iPhone or iPod, bite the bullet and re-download any apps that were blown away. then reauthorize one computer, and sync your device. Not exactly user-friendly. Not exactly Apple quality when it comes to the end-user experience.
I got lucky. There was only one app it wouldn’t let me transfer, and all my music, photos and contacts made the move when I transferred my files to the iMac from the phone. I ran the latest iOS upgrade and it seemed to work fine. The odd thing is, when I tried to sync my phone again, it told me “Hi this is iTunes and guess what there are items on your iPhone that haven’t been transferred to your computer, if you proceed you might lose these. Do you want to roll the dice and proceed? Are you in a gambling mood?” There is no list of the apps, music, photos, contacts or any other data, just an innocuous message asking you if you want to risk it and move forward. I bit the bullet and rolled the dice. The phone synced, I have no idea what was lost or if anything was lost at all.
Apple I am begging you to fix this. There are a bunch of other issues that I could go into about how iTunes sucks. Issues with it duplicating songs in your iTunes Library for no apparent reason, re-assigning album titles to song tracks even when you have “Manually Manage My Music” turned on in your iTunes preferences, how the whole iTunes application is less about file management these days and more about selling you stuff, but that is a whole post or three for the future.
This is why I try to never plug my iPhone into my Mac. I rarely sync, and when I do it usually happens when a new iPhone software release has come out, or I know I am going to buy a new iPhone or iPad. It really shouldn’t be this hard, and for a company that claims to make the most user-friendly computer experiences in the world, this is one that is far from it.