Words of Advice Before Upgrading to iOS 5 and iCloud

Today is a big day for Apple. The iPhone 4S is shipping and Apple is doing one of its biggest set of software updates ever. Today they’ll be releasing iOS 5 for the iPhone, iPod Touch and iPad. They’ll also be releasing MacOS X 10.7.2, introducing iCloud, and releasing updates for iTunes (out yesterday, actually), iPhoto, Pages, Numbers and Keynote.

iCloud is the glue that binds many of these updates together. iCloud replaces MobileMe (formerly .Mac) and is Apple’s solution to the synchronization problem - your data lives on iCloud and changes are automatically made available to your computers and devices, so you can do some work on your computer and simply find it available to you on your phone or iPad or another computer without having to do any synchronization.

These are compelling updates and if your computers or devices can accept them, I recommend them (though its often prudent to wait for a few days to see what kind of issues come up for others who use them).

There’s a big gotcha coming in iOS 5. One of the best features of it is the ability to use your iPhone, iPod Touch or iPad without ever connecting it to a computer. This is a great step forward. To do so you need to associate your device with an “Apple ID”. And there’s where a lot of people are going to get bitten.

If you’re a long-time Apple user you likely have several Apple IDs without even knowing it. You may have a login on Apple.com to buy from the Apple Store online. You almost certainly have an iTunes Store account. And if you’re a Mobile Me user you likely have a Mobile Me account, which is another Apple ID. That’s possibly three different Apple IDs right there.

You’re going to need to sign in using an Apple ID on your iOS device. If you don’t use your iTunes Store ID you won’t have access to any protected media (apps, audiobooks, ebooks, TV shows, movies and the like) that you’ve previously purchased from the iTunes Store. So be careful to use your iTunes Store Apple ID when you provide credentials to your device.

You’ll have a separate iCloud sign-in. You can migrate an existing MobileMe account to iCloud. Apple refers to the ability to re-download music, TV shows, apps and ebooks from the iTunes Store as a feature of iCloud. I have absolutely no idea if this feature follows your main sign-in on your iOS device or if it follows your iCloud account. If it follows your iCloud account then if your iCloud account uses a different Apple ID from your iTunes Store ID you may not have access to your media for re-downloading, and that would be painful.

If you make the wrong choice, it would only be annoying - change it and get back through whatever configuration and setup has to be done - except that Apple has a new policy of only allowing the Apple ID a device is bound to to change once every 90 days. So you’ll be stuck with whatever ID you set it up with for three months. You really want to get this right the first time. And, there’s currently no way to merge Apple IDs. So if you have multiple IDs, you’re stuck. So:

If you’re a new user, don’t sweat the details too much here. Just make sure you use the same login as you do (or will use) for the iTunes Store.

If you’re an existing user and don’t use Mobile Me, just use your iTunes Store account.

If you’re an existing user and do use Mobile Me, you may have a tough choice here. It may be worth talking to someone at Apple about it. If you haven’t really bought anything on your iTunes Store account then it shouldn’t be a big deal to us your Mobile Me account, but I’d have to wonder if there’s really anyone out there who falls into this category. Otherwise you’re looking at likely having to choose between your iTunes Store stuff and your existing Mobile Me setup (and email address).

The one bit of good news is that if you have an already set up iPhone, iPod Touch or iPad, are using Mobile Me to sync currently and switch to a new iCloud account, iOS will offer to keep your existing contacts, calendars and bookmarks and send them to iCloud, rather than just wipe them out.

There are a lot of rumors that Apple is aware that these tradeoffs are a problem and has been working frantically to provide a way to merge Apple IDs, but they have a lot of users and it’s likely that their back-end systems may need a pretty big overhaul to support this, so don’t expect it to be an easy change for them. They’re going to want to make sure they get it right the first time, if they ever support it.

If you do upgrade and set your iCloud ID to be different from your iTunes Store ID I’d be very interested in hearing how it goes for you.