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Take Control of Syncing Data in Snow Leopard
Nov 19, 2009

Take Control of Syncing Data in Snow Leopard

Learn how to sync your data with another Mac, iPhone, iPod, mobile phone, or PDA!

Is this ebook up-to-date? Excellent question. If you want to understand how syncing works conceptually or sync a non-Apple smartphone, or sync between your Mac(s) and MobileMe, this ebook remains pretty much spot on—though now that MobileMe has been discontinued, some of that content remains spot on as a history lesson, not as a practical instruction manual. However, since this ebook was updated in late 2009, Apple has released the iPad, iOS 4 (and iOS 5 and iOS 6…), and iTunes 10. Also, Apple made some changes to the Apple TV situation.

With clear directions and a humorous touch, expert Michael Cohen walks you through exactly how to sync managed data from a Mac running Mac OS X 10.6 Snow Leopard with a variety of devices and services. 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, you’ll find useful advice and directions. (“Managed data” is data that you can’t usually see as separate files in the Finder—data such as iCal events, Address Book contacts, Safari bookmarks, and anything you store in iTunes.)

You’ll also learn how syncing works under the hood and get troubleshooting advice in case your sync engine throws a rod.

More Info

You’ll learn about syncing managed data on a Mac running Snow Leopard with:

  • Another Mac
  • Microsoft Exchange
  • The cloud (i.e. MobileMe or Google)
  • An iPhone, iPod, or Apple TV
  • A non-Apple mobile phone
  • A PDA (i.e. a Palm or Blackberry, specifics are brief)

“It offers a great in-depth look at syncing on your Mac.” —CNET Reviews

Types of sync data covered include:

  • Calendar items stored in iCal, Entourage, Google, and Yahoo
  • Contacts stored in Address Book, Entourage, Google, and Yahoo
  • Data on Exchange servers
  • Data on MobileMe
  • 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 Mac OS X’s Sync Services, such as Yojimbo
  • Audio, video, photos, apps, and associated metadata from iTunes

Types of devices covered include:

  • Macs, with details on MobileMe and overviews of popular third-party options
  • The iPhone and iPod touch, via Microsoft Exchange, 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 via iSync and/or third-party utilities

Connection technologies and software examined include:

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

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

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?
  • Argh! Snow Leopard’s iSync doesn’t support the Palm! What third-party software can I use instead?
  • I want to sync directly with an Exchange server… what do I need to know?
  • What’s the smartest way to sync keychains between Macs?
  • 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.


Does this ebook explain how to sync an iPhoto library between two Macs?

Sorry, no, it does not. It talks about syncing iPhoto photos to an iPod, iPhone, or Apple TV, but not to another Mac. However, the Blog for the ebook has an informal article about syncing iPhoto photos between Macs.

Are there older editions of this ebook, for older operating systems?

Yes. Take Control of Syncing Data in Leopard looks at this topic for Mac OS X 10.5 Leopard. It was updated in late 2009, so it includes details on iTunes 9 and iPhone OS 3. Take Control of Syncing in Tiger discusses syncing in 10.4 Tiger from the perspective of 2007.

Update Plans

June 2011 – We don’t plan to update this ebook.

Posted by Adam 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 Adam 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 Adam 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 Adam 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 Adam 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.