Why does syncing play Gossip with my contacts?

When Steve Jobs announced the iPhone at Macworld 2007, I was one of the thousands of attendees gawking at the phone in its crystal case flanked with security guards. The announcement generated more questions than answers. As an Entourage 2004 user and a prospective iPhone owner I wanted to hear “… and it will sync with Entourage!” but nobody knew until a short while before the iPhone was released in June that it would indeed sync.

Since then I’ve learned a lot about “the truth”. That’s not a biblical or existentialist remark but rather the name Apple gave a special database that stores sync information on a Mac. While the name sounds authoritative the truth about the truth database is it’s only as good as the information synced to it and not everything syncs equally.

An electronic Shape-O Toy!

Think of the truth database as the well-known child’s Shape-O Toy. The Shape-O Toy is a big plastic ball that can hold a variety of small plastic shapes but each shape can only fit through its own hole. An application such as Apple’s Address Book or a device such as a Palm Zire has its own shape or its own unique schema. A schema can be thought of as simply the shape of the data. When using the example of the Shape-O Toy the star’s schema is five points, the square’s schema is four sides and the triangle’s schema has three sides, etc. The schema for anything connecting to the truth database is a list of elements such as Name, Address and Phone Number.

At this point I should stress everything syncs to the truth database via an application called the Sync Engine and not each other. Entourage does not sync with Address Book. Palm does not sync with the iPhone. The truth database gets synced with everything first and then everything syncs to the truth database.

When two or more applications or devices have compatible schema elements in common then they can exchange or sync information. First Name in Entourage is the same as First Name on my iPhone is the same as First Name in Outlook. But when two or more applications or devices do not have compatible schema elements in common then they can not sync information.

For example, the Custom fields in Entourage are unique to Entourage and are not recognized by other applications or devices even if they themselves have “Custom” fields. They’re simply not compatible.

So why doesn’t the truth database make everything compatible? Because that’s the job of the Sync Engine or rather the Sync Engine’s job is to find compatible information. The truth database can in fact hold all the different schema elements for all the applications and devices that sync with it but it’s just a container for the information and nothing more. When applications or devices connect to the truth database through the Sync Engine, the Sync Engine reaches in and pulls out the information that it thinks the application can understand and then leaves the rest. Although Entourage may have put the picture of one of your contacts into the truth database (yes, the picture is in there!), the Sync Engine knows the Address Book won’t understand Entourage’s picture format even though Address Book has a picture element too. Pictures between these two applications are just incompatible.

A game of Gossip

I realized that I have a lot of stuff syncing with Entourage. Not only do I sync Entourage at home to the Address Book and my spiffy new iPhone but I’m also syncing information across the Internet to my Exchange Server at work via Outlook Web Access (OWA). The Exchange Server in turn is syncing to another copy of Entourage on my Mac and to Outlook on my Windows workstation.

If I’m not careful all this syncing will have the same effect as a secret told in the game of Gossip. Remember that game from childhood? A short phrase repeated between different people in a series of whispers can easily end up being completely misunderstood by the time it reaches the last person. If I change something on my iPhone, sync it to the truth database, sync to Entourage, sync to Exchange and then sync to Outlook then that contact will more than likely be very different from the contact that I edited. Information may be missing or the contact may be duplicated by one of the applications attempting to keep me from destroying data, which is annoying but preferable.

What can I do to protect my information?

Simple:

  • Always make additions, changes and deletions on one machine and in the same application
  • Accept that most applications, if not all, will sync less information than your original contact

I make all my changes in Entourage on my home computer, including changes to my business contacts for work. My home Entourage application is the hub of my applications and devices because it syncs to both the truth database and my company’s Exchange Server. It’s also my primary E-mail application and only uses contacts found within its own database. It can’t use Apple’s Address Book.

Also, be aware of what will sync and what won’t sync. All good contact managers will sync the basics: Name, Address, Phone and Email, but that’s about all they will have in common. Other items such as secondary addresses, instant message addresses and children’s names may sync to just a few other applications or none at all.
I made the following table to illustrate just how much I found will sync with the information I put into Entourage. None of my applications or devices syncs all of Entourage’s contact information perfectly. Surprisingly the most compatible application that I use with Entourage is Entourage itself. (I find this surprising because I’m connectng my home Entourage to an OWA server at work, which is then connected to my Exchange Server and then connected to another copy of Entourage. This may be a reflection of the MacBU‘s commitment to making Entourage compatible in a corporate environment.) I found that Address Book syncs very well too while Palm OS and .Mac are the least compatible applications. And my iPhone, I’m pleased to find, syncs almost as much as Address Book.

What syncs with Entourage?
Entourage
Schema
.Mac Address
Book
Exchange
Entourage
Exchange
Outlook
Exchange
OWA
iPhone Palm OS
Name and work
First Name Yes Yes Yes Yes Yes Yes Yes
Last Name Yes Yes Yes Yes Yes Yes Yes
Title No Yes Yes Yes No Yes No
Suffix No Yes Yes Yes No Yes No
Nickname Yes Yes Yes Yes No Yes No
Company Yes Yes Yes Yes Yes Yes Yes
Job Title Yes Yes Yes Yes Yes Yes Yes
Dept No Yes Yes Yes No Yes No
Address
Work Street Address Yes Yes Yes Yes Yes Yes Yes
Work City Yes Yes Yes Yes Yes Yes Yes
Work State Yes Yes Yes Yes Yes Yes Yes
Work Zip Yes Yes Yes Yes Yes Yes Yes
Work Country/Region Yes Yes Yes Yes Yes Yes Yes
Work URL No Yes Yes Yes Yes Yes No
Home Street Address Yes Yes Yes Yes Yes Yes No
Home City Yes Yes Yes Yes Yes Yes No
Home State Yes Yes Yes Yes Yes Yes No
Home Zip Yes Yes Yes Yes Yes Yes No
Home Country/Region Yes Yes Yes Yes Yes Yes No
Home URL Yes Yes Yes Yes No Yes No
Phone
Home Phone 1 Yes Yes Yes Yes Yes Yes Yes
Home Phone 2 No Yes Yes Yes Yes Yes No
Home Fax Yes Yes Yes Yes Yes Yes No
Work Phone 1 Yes Yes Yes Yes Yes Yes Yes
Work Phone 2 No Yes Yes Yes Yes Yes No
Work Fax No Yes Yes Yes Yes Yes Yes
Pager No Yes Yes Yes Yes Yes No
Mobile Phone Yes Yes Yes Yes Yes Yes No
Main Phone No Yes Yes Yes Yes Yes No
Assistant Phone No Yes Yes Yes Yes Yes No
Custom Phone 1 No Yes Yes No No Yes No
Custom Phone 2 No Yes Yes No No Yes No
Custom Phone 3 No Yes Yes No No Yes No
Custom Phone 4 No Yes Yes No No Yes No
Email
Email Address 1 Yes Yes Yes Yes Yes Yes Yes
Email Address 2 Yes Yes Yes Yes Yes Yes No
Email Address 3 No Yes Yes Yes Yes Yes No
Email Address 4 No Yes Yes No No Yes No
Email Address 5 No Yes Yes No No Yes No
Email Address 6 No Yes Yes No No Yes No
Email Address 7 No Yes Yes No No Yes No
Email Address 8 No Yes Yes No No Yes No
Email Address 9 No Yes Yes No No Yes No
Email Address 10 No Yes Yes No No Yes No
Email Address 11 No Yes Yes No No Yes No
Email Address 12 No Yes Yes No No Yes No
Email Address 13 No Yes Yes No No Yes No
Instant Messaging
Instant Messaging 1 No No No No No No No
Instant Messaging 2 No No No No No No No
Instant Messaging 3 No No No No No No No
Instant Messaging 4 No No No No No No No
Instant Messaging 5 No No No No No No No
Instant Messaging 6 No No No No No No No
Instant Messaging 7 No No No No No No No
Instant Messaging 8 No No No No No No No
Instant Messaging 9 No No No No No No No
Instant Messaging 10 No No No No No No No
Instant Messaging 11 No No No No No No No
Instant Messaging 12 No No No No No No No
Instant Messaging 13 No No No No No No No
Custom and Miscellaneous
Custom 1 No No Yes No No No No
Custom 2 No No Yes No No No No
Custom 3 No No Yes No No No No
Custom 4 No No Yes No No No No
Custom 5 No No Yes No No No No
Custom 6 No No Yes No No No No
Custom 7 No No Yes No No No No
Custom 8 No No Yes No No No No
Custom date 1 No Yes Yes No No No No
Custom date 2 No Yes Yes No No No No
Spouse No Yes Yes Yes No No No
Birthday No Yes Yes Yes No Yes No
Anniversary No Yes Yes Yes No Yes No
Notes No Yes Yes Yes Yes Yes Yes
Age No No Yes No No No No
Astrology sign No No Yes No No No No
Interests No Yes Yes No No No No
Picture No No No No No No No
Categories No No No No No No No
Certificates No No No No No No No

For additional information about syncing Entourage with the iPhone see Using Entourage with iPhone on The Entourage Help Page.
Additional reading:

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6 comments to Why does syncing play Gossip with my contacts?

  • Joel McIntosh

    This is an incredibly informative post. Thank you for taking the time. I administer about 10 Macs that are using Sync Services to sync Entourage to other applications (via the “Truth”), and this post is a huge help in my understanding about how to do this efficiently. Thanks again for taking the time to post this information.

  • Thanks for kudos, Joel!
    Someone on another list recently asked about Entourage –> .Mac –> Entourage syncing and I hope to get the information updated to include that as well.

  • Scott Sanford

    So, here’s a good question for you. I, like you, have a nice iPhone that I use daily. I get a call from a colleague from a different number than usual. I use the cool interface to add that number ot the contact record. (2 different things could happen here, either adding it as a NEW type of number, or replacing an existing number).
    Typically, I use Entourage for my updates. This time, technically, I’ll be using Address Book for the update.
    What should happen to my data? I will tell you in reality, I LOOSE MY CHANGES. Every time.
    Additionally, I have a strange “refresh” that seems to happen more or less every 15 minutes. I loose all the contacts in AB for about 5 minutes, then miraculously they re-appear!
    Trouble is, they’re NOT THE SAME RECORDS. They have the same data, but they’ve been re-populated from Entourage. I know this because any group membership in AB or pictures I’ve added in AB disappear.
    I would LOVE, LOVE , LOVE some sort of solution to this as it’s crippling right now.

  • William M. Smith

    Hi Scott!
    This post was written while Entourage 2004 and Mac OS X 10.4 (Tiger) were the latest software versions. I’m going to guess you’re using Entourage 2008 and Mac OS X 10.5 (Leopard).
    Syncing was horribly broken with the earlier releases of both of these products but has gotten better with all updates applied. Still, lots of folks are having problems but I think they’ve given up complaining.
    No one’s quite sure if the problem is with Entourage or with Apple’s Sync Services. I suspect if the problem is with Sync Services then Apple’s new syncing architecture that’s coming with MobileMe may be their solution. That’s not to say you must have a MobileMe account but rather I think they’re probably re-doing all of syncing or possibly eliminating it for something better.
    Let’s hope.

  • Dallas

    Great post here, thanks for everything. I was a PC/Palm Treo user for the past 5 years, and now am with a different company, they purchased me a Mac Pro (pretty sweet), but really want to get a Blackberry Bold, since I feel that it will work better for my needs (lot more emailing/texting, business type stuff) than an Iphone.
    That being said I like to sync up and have everything in one place. Has the Blackberry and Entourage situation gotten any better? (PS I will be getting a BB Bold if it makes a difference)

  • That depends on what you’re using to sync Entourage. I don’t believe BB uses Mac OS X Sync Services yet, does it? I believe most folks are using MarkSpace products to sync their devices.
    Syncing using Sync Services in Mac OS X 10.5 (Leopard) and with Entourage is still a problem for a lot of folks. My consensus is that this is an issue with both Apple and Microsoft.
    I’m really hoping that the Mac OS X 10.6 (Snow Leopard) release fixes a lot of these issues. Snow Leopard is billed as a lot of “under the hood” fixes.