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Take Control of Syncing Data in Leopard
Oct 16, 2009

Take Control of Syncing Data in Leopard

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

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.

More Info

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.

What's New

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).

Update Plans

October 2009 – because Leopard is no longer the current version of Mac OS X, it is unlikely that we will update this ebook again.

Posted by Tonya Engst

  1. Google Sync Being Sunsetted and What It Means

    Google has announced that Google Sync, its syncing method that uses Microsoft’s ActiveSync technology, will no longer be available as a syncing option for most users. Support for it, except for paid users of its Google Apps service, will end on January 30 for Mail and Contacts; it is already unavailable for Google Calendar syncing. Instead, IMAP, CardDAV, and CalDAV are the preferred protocols for syncing. This means, in the case of iOS devices, that push email and calendar events will no longer be available to new users for Gmail, Google Contacts, and Google Calendar (Google, however, will continue to support accounts that have already been set up to use Google Sync). You can find out more about this change in the TidBITS article, Google Drops Google Sync for Most iOS Users, and in Joe Kissell’s Macworld article, What the End of Google Sync Means to You.

    Posted by Tonya Engst (Permalink)

  2. The End of MobileMe Means Big Changes in Syncing Capabilities

    Apple has announced the end of its MobileMe service, effective 30 June 2012, and has also announced that many of its functions will find equivalents in the new iCloud service from Apple, due to debut sometime in the last quarter of 2011. As it turns out, however, a number of syncing features provided by MobileMe are not going to be replaced by equivalent features in iCloud. Apple provides some details what iCloud will include and what it won’t in its Mobile Me transition page (you can also read more about the transition in the TidBITS article, “Apple Details Transition from MobileMe to iCloud,” 24 June 2011).

    Specifically, Apple is shifting the center of the syncing process from your Mac to iCloud; as Steve Jobs said in his World Wide Developer Conference keynote this month, “The truth is in the cloud.” Making the transition to iCloud will be contact, calendar, and bookmark syncing. However, the syncing of Dashboard widgets, keychains, Dock items, and System Preferences will cease to work either when you sign up for iCloud or when MobileMe is turned off on 30 June 2012, whichever comes first.

    This also may mean the end of the line for the “Take Control of Syncing Data” books; until we have a clearer picture of how syncing works in the iCloud paradigm, we can’t begin to plan a new edition, nor even to know if such a book would make sense.

    We do appreciate your support, and will let you know more as soon as we know more.

    Posted by Tonya Engst (Permalink)

  3. MobileMe Will Be Replaced by iCloud

    On June 6, 2011, Apple announced a new service called iCloud that will appear at some point later in 2011 (“fall” in the northern hemisphere), and will replace MobileMe from Apple’s perspective. Until then, MobileMe continues unchanged, except that Apple is no longer selling subscriptions or charging for renewals; all current members automatically have their accounts extended through the end of June 2012.

    When iCloud becomes available, existing MobileMe members will be able to migrate to the new service, which will be free (albeit with optional paid features, such as iTunes Match and additional storage). So far, Apple hasn’t released details about the fate of iDisk (including file sharing and iWeb publishing); MobileMe Gallery; Back to My Mac; the Backup application; Web-based access to Mail, Contacts, and Calendars; or Mac-to-Mac syncing of things like preferences and keychains.

    In the meantime, you can learn more about iCloud and what it might mean for MobileMe users in the following places:

    Posted by Tonya Engst (Permalink)

  4. Syncing an iPhoto Library to Another Mac

    Take Control reader J.S. wrote in, asking if Take Control of Syncing Data in Snow Leopard explains how to sync an iPhoto library between an iMac and a Mac laptop. Although the ebook does not explain how to achieve this feat, the email exchange about the topic has some good suggestions. The suggestions build on one another, so read to the end before trying anything.

    Tonya Engst: I wonder what would happen if you stored an iPhoto library in Dropbox! The mind boggles!

    Adam Engst: It’s fine to sync photos between two libraries occasionally (best done via a general file syncing program like ChronoSync), but in general, I recommend that you figure out which Mac will be your main repository and do what you can to use the other one only when necessary, thus reducing the amount of time you’re moving files around.

    Dropbox could conceivably work, though most iPhoto libraries are too large to use without paying a fair amount.

    J.S.: Yes I do keep a master iPhoto library on my iMac, but use my laptop to take home to show my family, and I like to sync photos in it with the master occasionally.

    Michael Cohen: Apple doesn’t have a solution for syncing whole iPhoto libraries. Apple does offer, as you know, various ways to share photos, and to sync individual collections of photos between devices (e.g., between your Mac and an Apple TV or iPod), but the company does not provide a way to perform a full sync between libraries. In addition, Apple’s walled-garden approach makes it difficult for third-parties to provide such a solution, because the internal format of the iPhoto library evolves from version to version, and third-parties then have to reverse-engineer that structure to update their utilities. Throw in things like the Faces database (the format of which, as far as I know, is an Apple proprietary secret), and third-party syncing solution providers have their hands full.

    As Tonya suggests, putting the iPhoto library on a server accessible to several Macs is probably the best short-term solution, although I can imagine problems arising in terms of speed and reliability, especially for very large libraries.

    Adam: Your best is probably a general file syncing app like ChronoSync, then… Sorry there isn’t a better answer!

    Michael: One final thought: if you really just want a way to bring your library to your family occasionally, you might consider a cheap storage device if your library isn’t REALLY massive. A USB memory device with a few gigs of storage might be perfect for copying your library to for road trips, and probably wouldn’t cost much more than a third-party utility for syncing libraries. Added bonus: you have a backup of your library.

    J.S.: I do have an external Passport HD for general backup, but I guess I would need to copy the entire file from my iMac (and replace) the one on my laptop to do so each time I update. Not a problem if this brings in all the data.

    Michael: The iPhoto library is a package—that is, it looks and acts like a single file from the user’s point of view but is actually a whole folder hierarchy with all your photos, versions, thumbnails, projects, and associated metadata stored therein. So, yes, if you simply drag your iPhoto library to another device, all the information that your library comprises should make the journey intact.

    And you can hold down Option when opening iPhoto to have it prompt you to choose a library to open. I frequently do this, because I have several libraries: one for general use, one for testing, and one for writing projects that involve iPhoto. So you wouldn’t have to replace the library on the laptop: just open the one on the Passport HD.

    Adam: Yes, there’s no problem with copying the entire iPhoto Library package, but if it’s multiple gigabytes, it will take a while (and it will trigger Time Machine to back up the entire darn thing again). A syncing utility would be smart enough to copy only new data inside it.

    In iPhoto ‘09 you can just double-click iPhoto library packages to open them—no need for the Option-launch trick any more!

    Posted by Tonya Engst (Permalink)

  5. Michael Talks about the World of Syncing

    Listen to MacVoices #9107 and find out what author Michael Cohen has been working on lately, and why about 95% of the Syncing Data in Leopard ebook will appear in the Syncing Data in Snow Leopard ebook. Michael discusses what managed data is, and he pulls aside the curtain to help you understand how data syncs between your Mac and other devices.

    Posted by Tonya Engst (Permalink)

  6. Home Sharing vs. iTunes Sharing

    Home Sharing, a new feature in iTunes 9, makes it possible to easily sync purchased iTunes Store media among family members (or any group where everyone is authorized on the same iTunes Store account). While the feature is a clear win for sharing around iPhone apps, several Take Control authors have been perplexed by Home Sharing, either because the feature didn’t perform as they’d expected, or because it’s very difficult to concisely explain the differences between it and the old iTunes Sharing feature. Thankfully, Take Control author Ted Landau’s recent Mac Observer article tackles the subject with detail. If you’re interested in gaining a deeper understanding of how to share media in iTunes, check it out!

    Posted by Tonya Engst (Permalink)

  7. Google Sync Beta for iPhone

    Google announced the availability today of Google Sync for iPhone. This service allows you to sync your Google Calendars and Contacts with your iPhone wirelessly, using push technology. The service requires you that you set up an Exchange account on your iPhone and that your iPhone is running the version 2.2 firmware or later.

    You can see the instructions here, and you can see a list of known issues and limitations with the beta here.

    Posted by Tonya Engst (Permalink)

The Author

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 written several books, including Take Control of PDFpen, Take Control of Pages, and Take Control of TextExpander.