Over the past week I purchased several iPhone applications through the App Store, including Super Monkey Ball, a Rotary Dialer, and a few others.  I also downloaded some free applications.

Today I connected the iPhone to the Mac Mini for the first time.  I had to update iTunes, but that was relatively painless, other than dealing with having forgotten my login password on the Mac (necessary for software updates).

Once iTunes was updated, I plugged in the iPhone.  I told iTunes that I do NOT want to automatically sync the iPhone.  I went to the Applications tab, and clicked that I wanted to sync all applications.

Apple’s idea of what “Sync” means is clearly completely different than mine.  Rather than copying the applications I’d purchased on the phone over to the Mac for safekeeping, it started deleting them, starting with Super Monkey Ball!  As nearly as I can tell, Apple’s idea of “Sync” is to try to make the phone contain ONLY the content that is on the Mac.

I found in a fairly non-obvious place an option to “Back Up” the iPhone to the Mac, so I tried that.  It took a while, and when it was done, it told me

Some of the purchased items on the iPhone ‘Eric Smith’s iPhone”, including the item “Enigmo” could not be transferred to your iTunes library because you are not authorized to play them on this computer.

What a crock!  I’m not trying to run them on the Mac, I just need to save a backup!

It occurred to me that I might have better results if I downloaded applications in iTunes rather than on the phone itself, and they sync them over to the phone.  I downloaded a free application “Tris”.  Then I went to the “Applications” tab, and told it to sync “Selected applications” and checked “Tris”, rather than “All Applications”.  It immediately deleted my rotary dialer application, and I stopped the sync before it could delete more.  Apparently syncing “Selected applications” means “delete any other applications you haven’t selected.”  Now I had “Tris” on the Mac with no apparent way to get it into the iPhone without losing more of the applications already on the phone.

I finally tried the backup again and noticed in the fine print that I could “Authorize” the Mac.  Once I did that, the backup worked, and now it looks like I can sync my remaining applications without them getting deleted.  Apparently if I really want Super Monkey Ball and the Rotary Dialer, I’ll have to buy them again.

I thought Apple products were supposed to be easy to use, but this is about as counter-intuitive as it gets.