Is your data stuck on your Mac? Learn how to sync it with another Mac, iPhone, iPod, mobile phone, or PDA!

Take Control of
Syncing Data in Leopard

Michael E. Cohen

Frustrated in your attempts to sync data between Macs, or with an iPhone, iPod, or Apple TV? What about a mobile phone or PDA? Synchronization expert Michael Cohen shows you what you need, explains Apple’s syncing model, and provide essential troubleshooting advice. Now covers iTunes 9 and iPhone OS 3!

This product has been discontinued.

With clear directions and a humorous touch, Take Control of Syncing Data in Leopard explains how to sync data from a Mac running Mac OS X 10.5 Leopard with a variety of devices from Apple and other companies. Whether you want to sync phone numbers between your Mac and your mobile phone, share calendars and keychains between Macs, or move only new podcast episodes to an iPod, syncing expert Michael Cohen has the answers. You’ll learn what software and gear you need and the best ways to move data between devices. The ebook also explains how syncing works under the hood and provides troubleshooting advice in case your sync engine throws a rod. Covers iTunes 9 and iPhone OS 3!

Is this ebook up-to-date? Excellent question. You should buy this ebook only if you want a history lesson about how syncing worked at one time, back when MobileMe was active and all the various third-party products covered in this ebook were current. Much of the specific information in this ebook is no longer correct.

Includes a coupon for 50% off any product from PocketMac, makers of sync solutions for Mac and Windows.

Types of sync data covered include:

  • Calendar items stored in iCal, Entourage, and Google
  • Contacts stored in Address Book, Entourage, Yahoo, and Google
  • Data on Exchange servers
  • Dock items and Dashboard widgets
  • Apple Mail account settings, Safari bookmarks, and application preferences
  • Apple Mail and Entourage notes
  • Keychains (user names and passwords)
  • Items from software that uses Leopard’s Sync Services, including NetNewsWire and Yojimbo
  • Audio, video, photos, and associated metadata from iTunes

Types of devices covered include:

  • Macs, with details on MobileMe and overviews of popular third-party options
  • iPhone and iPod touch, via MobileMe or iTunes
  • Old and new iPods via iTunes, with details on USB and FireWire connections
  • The Apple TV via iTunes
  • Mobile phones, smartphones, BlackBerries, and Palm OS PDAs

Connection technologies and software examined include:

  • Bluetooth, USB, FireWire, Wi-Fi, and Ethernet
  • MobileMe, iTunes, iSync, IMAP (IMAP discussion is limited to Apple Mail)
  • Third-party products from BusyMac, Mark/Space, PocketMac, and Spanning Sync

Sampler of special questions you’ll find answers to:

  • What is the truth database? And what should I do if I think it’s lying?
  • When a sync occurs, what’s going on behind the scenes?
  • What is push syncing and how does it work?
  • What is the difference between syncing and a backup?
  • What does Bluetooth discovery mean, and what should I do about it?
  • Can I control exactly which audio and video files sync to my iPod?
  • How do I override automatic syncing when I connect my iPod to iTunes?
  • How does iTunes decide if a video file is a movie, TV show, or music video?
  • How does the Apple TV figure out what to sync if it fills up?
  • How do I sync everything possible to my iPhone—calendars, contacts, Safari bookmarks, the works?
  • How do I sync a mobile phone that Apple doesn’t support?
  • Why won’t my Palm device show up in the iSync app?
  • I have to sync with an Exchange server… what do I need to know?
  • What’s the smartest way to sync keychains between Macs?
  • How can I best avoid data duplication problems when syncing?
  • I have a syncing feeling about my data—what should I do?

This ebook explains all about syncing in iTunes and with an Apple TV. For a more media-centric approach, check out the Macworld Digital Music and Video Superguide. Also, for detailed advice on setting up an Apple TV with respect to networking, Take Control of 802.11n AirPort Networking has you covered.

Michael Cohen

About Michael E. Cohen

Michael E. Cohen has taught English composition, worked as a programmer for NASA’s Deep Space Network, helped develop the first commercial ebooks at the Voyager Company, and co-founded a major university’s Humanities computing center. He has authored several books, including Apple Interface Mysteries, Take Control of PDFpen, Take Control of Pages, and Take Control of TextExpander.

What’s New in Version 1.1

Most of the revisions in this version of the book address syncing changes and improvements provided by Apple’s continuing development of its MobileMe service, by Apple’s latest iPhone software (version 3.1 as of this writing), by iTunes 9, and by third-party developers (especially Google, which has furiously been enhancing its syncing capabilities).

These sections are new or substantially updated:

  • Sync an Apple Device with iTunes
  • iPhone and iPod touch Push Syncing
  • Sync Managed Information without MobileMe
  • Sync Exchange Directly

Further, the Sync Keychains section has been revised to include modified advice.

Also, though this book is about syncing with Leopard (yep, I just checked—that’s what the title says), I’ve also included some occasional tips and notes about things you can expect to find changed if you update to Mac OS X 10.6 Snow Leopard.

Additional changes and enhancements are sprinkled liberally throughout the text of the book. Sync you very much!

How do I find the PocketMac coupon?

After you download and unzip your ebook, open it in a PDF reader (typically Apple's Preview or Adobe Reader). You'll find the coupon on the last page.

A lot changed while Leopard was the current OS. How updated is this Leopard ebook?

Good news! The current version of this ebook, version 1.1 was revised in mid 2009 and thus covers iPhone OS 3 and iTunes 9. Snaps to author Michael Cohen for a lot of perseverance on this 1.1 update, which was free to everyone who'd bought 1.0.

Does this ebook cover Tiger?

This ebook doesn't much cover Mac OS X 10.4 Tiger. For information about syncing in Tiger, see Take Control of Syncing in Tiger, but note that that ebook does not cover MobileMe syncing.

I want to sync files, like iWork documents or the contents of my user's Documents folder. Will this ebook help?

Sorry, no go. This ebook doesn't cover that topic. Here at Take Control headquarters, however, we are really liking the Dropbox file synchronization utility. If you have a reasonably fast Internet connection, check it out!

Will this book help me sync a handheld PDA with a Macintosh computer and a Windows PC?

Well... not so much... Someone once wrote in with a question about this— here's the question and Michael's answer:

Question: I'd like to synchronize my Palm TX with my many Macs running OS X, and my work PC running Windows XP. I already do this, but would like to use iSync/iCal/Address Book instead of the moribund Palm Desktop on the Mac. Does this book talk about the pros and cons of this approach?

Answer: Generally speaking, you should not sync a handheld device (mobile phone, Palm, etc.) with more than one computer. Syncing with more than one computer vastly increases the possibility of sync conflicts between all the devices involved, and can increase the chances of data corruption as well. Apple includes this warning in its iSync help: "IMPORTANT: You should sync your phone with only one computer. If you sync your devices with more than one computer, your information may not sync correctly (you could see duplicates or wrong information)."

Things can only get even more confused if you sync a single Palm device between both a Mac OS computer and a Windows XP computer, which have rather different ways of syncing information.

The book does not talk about syncing handheld devices with Windows (the title, is, after all, Take Control of Syncing Data in Leopard).

  • Read Me First
  • Introduction
  • Quick Start to Syncing
  • A Briefing on Syncing
  • What You Can Sync
  • Connect Your Gear
  • Sync an Apple Device with iTunes
  • iPhone and iPod touch Push Syncing
  • Sync a Handheld Device with iSync
  • Sync Your Mac with MobileMe
  • The Conflict Resolver
  • Sync with Third-Party Software
  • Lost in Translation
  • Think Before You Sync
  • Appendix A: If Things Go Wrong
  • About This Book
  • October 2009 -- because Leopard is no longer the current version of Mac OS X, it is unlikely that we will update this ebook again.