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Take Control of Syncing Data in Leopard

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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!

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?

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13 Slices

Format Buy Remix

1. Quick Start to Syncing


Mac OS X 10.5 Leopard provides great synchronizing capabilities to help you share your information between devicesunfortunately, to a casual observer those capabilities may seem to be confusingly scattered all over. In fact, though, there's order in the chaos: to take control of syncing you need to learn a few simple concepts; make a decision or two; and, usually, follow a few short steps.

Understand what syncing is:

Take A Briefing on Syncing for basic syncing concepts (next page).

Check out Syncing Managed Information (p. 11) to find out what kinds of information Leopard syncs.

Syncing vs. Backups: learn the difference (p. 16).

Get your stuff together:

The Information You Can Sync (p. 17) helps you choose what to sync.

Learn about The Devices You Can Sync (p. 18), and then Connect Your Gear (p. 24).

Get synced:

Discover how to Sync an Apple Device with iTunes (p. 36). Or, learn about iPhone and iPod Touch Push Syncing (p. 74).

If Apple didn't make your gear, read Sync a Handheld Device with iSync (p. 82).


2. A Briefing on Syncing


The idea behind syncing is simple: take information you collect on one device, like the calendars and contact lists you keep on your MacBook or iPhone, and combine it with similar information on other devices, like your iMac or your iPod, so that the two sets of information match. Though the idea behind syncing may be simple, putting syncing into practice requires coming up with reliable solutions to some knotty problems. Here are the bigger knots:

How do you get the information from one device to another?

How can you guarantee that the most recently changed pieces of information replace the outdated ones?

How do you resolve conflicts when the same pieces of information are changed in different ways on different devices?

How do you translate between the internal storage formats that different devices may use for the information you want to sync?

All tough questions, but questions you don't have to answer because the developers who create syncing applications already havein fact, Apple itself has answered those questions several times in several ways over the last few years. The answers that Apple came up with in Leopard, and the path they took to get there, can help you better understand how syncing works (the first step in taking control of syncing), whether Apple or a third-party developer supplies the solution you end up using to meet your syncing needs.


3. What You Can Sync


When you want to start syncing, you must consider both the kinds of information you want to sync and the devices between which you want to sync.

Managed information is what Sync Services was created to handle. Managed Information and Sync Services lists many of the kinds of managed information that Sync Services syncs, along with some of the applications on your Mac that can host it. It can't be a complete list because any third-party developer can take advantage of Sync Services, and new sync-aware applications are introduced all the time.

Table3-1.Managed Information and Sync Services


Hosting Applications




iCal, Entourage, Google Calendar, SOHO Organizer


Address Book, Entourage, SOHO Organizer, Yahoo and Google contacts

Dock items, Dashboard widgets, application preferences

Leopard itself, various applications

Email settings

Mail (only mail rules, accounts, and smart mailboxes)


Keychain Access

Notes, clippings, PDFs, Web archives, and URLs


4. Connect Your Gear


Knowing what you can sync, as described in the previous section, is not enough, of course: you have to know how to hook things up so you can sync. Whether you want to sync your Mac with an iPhone, a PDA, or another Mac, at some point you must establish some sort of connection between themor with an intermediary that can connect to both. Fortunately, your Mac loves to make connections.

That's not to say that all connection methods are simple matters of plug-and-play; though some are, others are more like plug-and-do-a-lot-of-other-stuff-and-then-play. And then there are some connection methods, like Bluetooth, that don't involve any plugging at all. In this section, you can find the connection methods you need to sync your devices, and, where necessary, the details of what you need to do to get them to play.

Your connection methods are:

Connect over a Network (see below)

Connect with USB (p. 29)

Connect with FireWire (p. 31)

Connect with Bluetooth (p. 31)

You'll connect over a network either to use Apple's MobileMe syncing capabilities, to sync your Apple TV, or to use some third-party syncing utilities. I cover each in turn, next.


5. Sync an Apple Device with iTunes


Ever since iTunes 2.0 came out, Apple's music player has offered at least one syncing capability, albeit a narrowly specialized one: the capability to sync music playlists to an iPod. As both the iPod and iTunes matured, iTunes' sync capabilities became more powerful and varied, while still maintaining the original narrow iPod focus. By the time the first video-capable iPod was released, iTunes could sync music, podcasts, photo albums, videos, iCal calendars, and Address Book contact lists.

Apple has added several other types of devices to the iTunes syncing stablethe Apple TV, the iPhone, and the iPod touchand has provided sync capabilities tailored for each of these devices. For example, when you connect an iPhone or iPod touch, iTunes adds the capability to sync Safari bookmarks and Mail account settings along with all the other things it can sync.

In this section, I describe what iTunes syncs and reprise the methods you use to connect your devices to your Mac. Next, I explore both the general syncing options that iTunes provides for all devices and the options that are device-specific. Finally, I describe the options iTunes provides for syncing specific types of data, including media.


6. iPhone and iPod touch Push Syncing


When the iPhone debuted, some people asked why it couldn't sync over the air. After all, the touchable glass slab had not one, not two, but three separate wireless transceivers: cellular, Bluetooth, and Wi-Fi. Nonetheless, it could sync to the Mac only via a wired USB connection. When the Wi-Fi-licious iPod touch came out, it, too, synced over a USB cable connection. It took both a major update to the mobile OS X that drives the iPhone and the touch, and the metamorphosis of Apple's online .Mac service into MobileMe, before wireless syncing came to these devices. It came in the form of push.

Everyone's Getting So Pushy!

This section covers using MobileMe to do push syncing between a Mac and an iPhone or iPod touch. However, the iPhone and iPod touch can now wirelessly sync contact and calendar information with a variety of sources other than MobileMe. For example, these devices can sync Google and Yahoo contacts and calendars directly with these services, and they can talk to Exchange servers wirelessly as well. See Sync Exchange Directly and Sync Managed Information Without MobileMe for more details.


7. Sync a Handheld Device with iSync


Originally the core of the Mac OS X syncing experience, iSync now has a more focused mission: to sync calendar and contact information between your Mac and your portable, non-Apple devices. When iSync syncs with a handheld device it uses the contact info managed by Address Book and the calendar info managed by iCal. However, that doesn't necessarily leave contact and calendar data from other programs out in the cold: if those other programs can sync with Leopard's Sync Services, their information can be included in the Address Book's and in iCal's data collections, and make its way from there to the device (for example, see Sync Entourage).

To use iSync with your device, you have to do the following:

Connect the device to your Mac (see Connect Your Gear).

Add the device to iSync's collection of known devices; see Add Phones and Add Palm OS Devices (and see Remove Devices if you no longer want to sync that device).

Tell iSync what info you want to sync with that device (hint: your Address Book contacts and iCal calendars are involved). Configure Device Sync Settings explains the kinds of options available.


8. Sync Your Mac with MobileMe


MobileMe is Apple's entry into the software-as-a-service sweepstakes, and the particular service that MobileMe provides is a personal information sharing and exchange center. Included with MobileMe's many features (which would take an book like Joe Kissell's Take Control of MobileMe to describe) is the capability to sync all the stuff listed in Managed Information and Sync Services (such as Safari bookmarks and application settings) between your home Mac and office Mac and any other Macs you happen to have handy.

Although you can replicate just about every information sharing and exchange feature that MobileMe offers some other way, the part of the MobileMe service you can't replicate is how well integrated it is with Leopard.

The integration begins with how you obtain a MobileMe subscription: as noted in Connect Over a Network, you can purchase a MobileMe subscription from the Account view of Leopard's MobileMe System Preferences pane. You also use this pane to choose the managed information types that you want to sync and when you want to sync them (see Syncing Managed Information for more about managed information). You also use the pane to reset synced information; read Reset Information.


9. The Conflict Resolver


Both iSync and MobileMe syncing can occasionally encounter conflicts in the information being synced that exceed the capability of the sync engine and the truth database to resolve automatically. Such conflicts can occur when you change the same item of information on two different devices between syncs: for example, suppose you change a contact's phone number on your phone, and in your Address Bookbut, by mistake, you make a typo in the Address Book entry. Because both changes happened between sync sessions, the sync engine cannot ascertain which change takes precedence when you finally do sync. That's where Sync Service's Conflict Resolver takes over.

Whenever sync conflicts arise, Sync Services presents a Conflict Resolver dialog asking you to resolve the conflicts. You can choose to resolve the conflicts immediately, or wait until a later time to resolve them.

The Conflict Resolver displays each set of items that conflict and asks you to select the right one. Click the item with the correct information and then click Continue to resolve the conflict. You can choose to fix all conflicts manually, stepping through them one by one with the Previous and Continue buttons, or you can select the Resolve All Similar Conflicts Using source name checkbox. "Similar conflicts" are those that have a similar cause, such as a different timestamp. When you select the checkbox and click Continue, the Conflict Resolver uses the information source you picked for resolving the similar conflicts.


10. Sync with Third-Party Software


Leopard's Sync Services is smart and powerful, but it doesn't offer syncing support to meet all contingencies. When it runs aground, you may have to abandon the Apple mothership and board a third-party rescue vessel.

There are many reasons why you might want to, ahem, sync different:

iSync shortcomings: Although iSync can sync Address Book and iCal information with lots of mobile devices, it can't handle every mobile phone on the market. If your device falls into the iSync ignorance zone, flip ahead a page to Sync Phones with Third-Party Plug-ins for help finding an iSync plug-in for your phone.

And even when iSync provides device support, it only supports Address Book and iCal syncing. The Palm OS, for example, has capabilities far beyond iSync's narrow focus on addresses and calendars; Sync Palms with Third-Party Software can help you unleash your Palm's power.

What's more, no iSync plug-in can open the syncing door for Blackberry and Windows Mobile devices. Read Sync Blackberries with Third-Party Software and Sync Windows Mobile Devices with Third-Party Software for help with those handhelds.


11. Lost in Translation


A special edition DVD of Monty Python and the Holy Grail has a clip from the movie first dubbed into Japanese, and then subtitled with an English translation of the Japanese dubbed dialogue: not surprisingly, the English subtitles don't quite match the original English dialogue. The result is hilarious.

During a sync, when managed information (see Syncing Managed Information) moves from one program to another similar-but-not-quite-identical program, the same kind of thing can happen: contact info may come back missing pieces, or with items mislabeled, or calendar events may be set for a different time zone. However, hilarity (usually) doesn't ensuenot, at least, if it's your data. Address Book and iCal are the programs most prone to this problem, and for at least one good reason: iSync is all about exchanging Address Book contacts and iCal calendars with handheld devices and each of the many dozens of different handheld devices that iSync syncs with has its own phone book and calendar function, each with its own ways of storing and labeling contact and calendar information.


12. Think Before You Sync


The preceding sections of this book have dealt with the software, the hardware, and the underlying concepts involved with syncing in Leopard. There's but one piece of the syncing puzzle left to put in place: you, the user. How well Leopard's syncing capabilities work for you depend in part on how well you can align your syncing needs, and your computational habits, with the tools that Leopard and third parties provide. I am not you: I don't know what you wish to sync, or why. But I can offer some short bits of advice based on my own syncing needs, experiences, and habits.

As you've seen, Sync Services makes various assumptions about what you'll sync and how you'll sync. Managed information syncing (see Syncing Managed Information) works best with various small bits of information that can be stored in and managed by a databasesuch as contact information, passwords, or preference settingsrather than large undifferentiated blobs of binary informationlike image files, movie projects, or novels in progress. A case in point: although you can use a sync-enabled application like Bare Bones' Yojimbo to sync large chunks of data via MobileMe, that's not the best use you can make of MobileMe syncing. Your sync sessions with MobileMe will certainly take longer than you'd like, and the amount of free space on your iDisk will begin to plummet.


A. If Things Go Wrong


If this were the philosopher Gottfried Leibniz's best of all possible worlds, I would have nothing to put into this appendix. However, experience has shown me that the philosopher Murphy trumps Leibniz: things will go wrong in any given situation, if you give them a chance. This appendix describes some common syncing problems and my advice for conquering them.

Syncing requires different programs and devices to all work together. Any one of the actors in this syncing drama can, metaphorically, forget or flub a line or miss an entrance: when that happens, syncs won't work right. Here I describe the general causes of miscues that make syncs go wrong, and offer some tips on how to fix them.

To sync two or more devices, you must connect them, so when a sync fails, the connection is one of the first things I check. As I describe in more detail in Connect Your Gear, connections can be wired or wireless, and they can be direct between devices or established over a network. Adapt the following advice to the way you connect your devices.



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