PRODUCT REVIEW
Syncing the iPhone: As Simple as You Want It to Be

Sure, I followed the steps, but I expected failures, problem windows and troubleshooting. Something had to go wrong, right? I checked the Calendar app on the iPhone -- events were listed. I listened to music via the iPod application -- songs from my selected playlists were all there. Same success with videos, the photos I wanted and, to my big surprise, e-mail. I have six completely different e-mail accounts, four of which I access via Apple's (Nasdaq: AAPL) OS X built-in Mail program, plus a Yahoo (Nasdaq: YHOO) Mail and a Google (Nasdaq: GOOG) Gmail account.

All of the accounts were easy to add, and before I realized what was happening, they were busy downloading the last 50 e-mail messages automatically via AT&T's (NYSE: T) EDGE (Enhanced Data Rates for GSM Evolution) network -- all this before I even tried to connect to my home WiFi network. I later found one fairly common password problem, but the point is, within a few minutes, I was connected to my e-mail inbox. I was astounded.

The Oddity of iTunes

Syncing via iTunes seemed odd at first. While syncing iPods via iTunes is natural enough for music, podcasts and videos, Apple's iSync application would have seemed a more natural choice for calendaring, bookmarks and e-mail. It makes perfect sense, however, when you consider Apple's connection to the PC world is typically via iTunes and iPods. Plus, if Apple wants to control the content universe, iTunes is a capable enough interface.

Syncing content with iTunes via a USB cable is the only way to do it if you're working with data and files. It'd be nice to use Bluetooth for quick little updates, but Apple doesn't support that option. In addition, there's no way to manually drag and drop songs or videos, which is darn handy for iPods. I'm guessing that Apple chose to lock down the iPhone to reduce the risk of complications for most users -- perhaps, as the iPhone mania settles down, Apple might open up some new options.

No Address Book?

Apple's OS X built-in address application is called Address Book. When I looked for "Address Book" on my iPhone, I couldn't find it. Address Book is converted into "Contacts" and is integrated with the phone functionality. The familiar Address Book interface is also gone, of course, but it's replaced with a slick iPhone interface that retains your Groups and lets you do the cool finger-flick motion to scroll through your list of contacts.

Again, if you think of Apple as playing in both a Mac and a PC world -- not to mention a cell phone world -- Address Book is isolated to the Mac, so changing the name to Contacts makes perfect sense.

Contacts > Address Book

Functionality is integrated everywhere. Tapping a contact's phone number dials that number; tapping an e-mail address generates an e-mail from your default e-mail account; tapping the Text Message button starts a text message, and tapping an address launches you into the Google-powered Maps app, which shows you a street view of the address. Tap Satellite, and boom, you've got the overhead satellite photo.

What if you're talking to your contact face-to-face? Simply touch the person's cheek with the iPhone, and it will read the person's DNA and generate a picture that approximates your contact's face. Just kidding. The iPhone isn't that smart, but you can easily tap Edit and then take a quick photo of your friend with the iPhone's built-in camera. Crop and zoom in or out, and in less than a minute you can update your contact details with a photo. If you have a photo of the person already in your iPhone, you can use that as well.

Next time you sync, your contact will have the photo in Address Book.

You can add an entirely new contact, too. Once you sync, from within Address Book you'll have to drag and drop it into the appropriate Group manually, and the next time you sync, your contact will be in the correct Group on your iPhone.

You can choose, through iTunes, if you want to sync all of your contacts or only certain groups. If you use Yahoo Address Book contacts, you can sync those as well.

For PC users, you must use compatible contact managers. For contacts, these are Outlook Express (Windows XP only), Windows Contacts (Windows Vista only), Outlook 2003, Outlook 2007 or Yahoo.

If you're an IBM (NYSE: IBM) Lotus Notes user, you're out of luck (at least for now).

iCal Morphs to Calendar

In Mac OS X, the calendar application is iCal, but in the iPhone, it's just Calendar. In iCal, you can create special calendars by category or purpose, as well as color-code them. When you sync your iPhone, those segmented iCal "calendars" are replaced by a standard calendar entry -- no color, no category, just the date, time and text-based details. You can view them by a list, by the day or by the month. You can edit, delete and add entries, of course, and those changes are transferred to iCal the next time you sync.

Your iCal To Do lists, however, are not transferred to the iPhone.

For PC users, only Outlook 2003 and Outlook 2007 are compatible with the iPhone's Calendars app.

Complications Abound

For relatively simple synchronizations for Mac OS X users, the iPhone is mind-blowingly fast and easy. For most basic PC users, I'm hearing similar results. For power users with complicated calendars, though, connections to corporate shared calendars, and those who use Lotus Notes, iPhone synchronization can run into difficulties. Some users, for example, have managed to sync their calendars and contacts from a laptop while synchronizing music and videos from another computer altogether.

Others have come up with elaborate workarounds for non-supported calendars -- like exporting calendar details to Google Calendar and using third-party software like Spanning Sync to snag the Google Calendar events and sync them with iCal, which then makes it back to the iPhone. However, more direct, complicated syncing tends not to be natively supported. Users who want to sync calendaring data from multiple computers -- for example a home-based Mac and a Windows-based work PC -- are out of luck.

The Overall Joys of Dumb Syncing

If you step back and look at the big picture, the iPhone syncs amazingly well and easily, with few complications for the vast majority of users. Apple's simple but locked-down syncing process via iTunes works, and it's easy to understand and learn.

As more customers start integrating with multiple environments, more syncing complications will arise, but those may also be figured out by a community of iPhone addicts plugging away at workarounds. Plus, as Apple settles down and releases the next generation of OS X -- Leopard -- in October, we may also see some new syncing options enabled by Leopard or even specialized iPhone services. Apple's .Mac service is a prime candidate for assisting with more complicated syncing needs.

In some ways, Apple's success in building such a smart-yet-simple iPhone has the side effect of encouraging customers to imagine new ways to use it. That's a pretty good problem to have.