UPDATED for iTunes 10.5 and iOS 5

Thinking about iTunes Match? See Getting the Most out of iTunes Match

Let’s start out assuming you have an iPhone and a Mac or PC running iTunes.  Here’s what you need to do:

1.  Upgrade to iTunes version 10.5 – Open iTunes and select iTunes > Check for Updates.

2.  Get a compatible device – After you get your Mac or PC updated, you will need one of the following* to use iCloud and set up automatic downloads of new purchases:

  • iPhone 3GS, iPhone 4 or 4S
  • iPod touch (3rd and 4th generation)
  • iPad, or iPad 2

3.  Update to iOS5 – You’ll need to plug into your computer for this one.  (If you’re already on iOS 5, you can upgrade to 5.0.1 over the air, but you’ll need to plug in to power first.)

4.  Set up or turn on iCloud – After the update, follow the onscreen instructions to setup iCloud, signing in with the Apple ID for the purchases you want to sync.  Want to use a different ID?

If you skipped the setup process, or want to change your settings, go to Settings > iCloud.  Choose the items you want to backup and sync with iCloud.

5. Configure Automatic Downloads – go to Settings > Store.

With automatic downloads set to ON, downloads on one computer or device will show up on the others.

6. Download purchase history and selectively download purchases not set on Automatic.

For songs, go to Music > Store (button at top left) and press the Purchased icon. (That’s where iTunes is hiding in iOS 5.)

Press Music again, then Not On this iPhone, and select All Songs, Recent Purchases or an individual Artist.  Finally, press Download All or the cloud download icon for individual tracks.

For Apps, go to App Store > Updates and press Purchased.

Select Not On This iPhone and press the cloud download icon for any apps you want to install.

Download [Name of Song] for Free!

*The fine print from Apple:

iCloud requires iOS 5 on iPhone 3GS or later, iPod touch (3rd and 4th generation), iPad, or iPad 2; a Mac computer with OS X Lion**; or a PC with Windows Vista or Windows 7 (Outlook 2007 or 2010 or an up-to-date browser is required for accessing email, contacts, and calendars). Some features require a Wi-Fi connection. Some features are not available in all countries. Access to some services is limited to 10 devices.

Music features of iCloud require iOS 4.3.3 or later on iPhone 3GS or later, iPod touch (3rd and 4th generation), iPad, or iPad 2; iOS 5 on iPhone 4 (CDMA model); or a Mac or PC with iTunes 10.3.1 or later. Download iTunes 10.5 free.

**The fine print from MMT: MobileMe users will need OS X Lion to migrate their Macs to iCloud, but the iTunes features of iCloud are working fine for me with Snow Leopard.