To put it mildly, there’s a lot of complexity in this post. However initial results are very positive. This method will require me to purchase a MobileMe account, something I was hoping to avoid. (See below for a partial index to past efforts.)
The end result is that I have a single collection of work/home contacts across iPhone and OS X Address book at home. The work contacts portion of this collection is updated weekly. At this time the update is one way, from Work to Home.
For anyone who may be facing these challenges, I have provided a skeletal outline here of what I did and what I would do if starting from scratch. You will see how insanely complex this is. Note that as of this writing the care PIM data that was once in Palm/Desktop is now scattered across Google (Calendar and a detached set of Contacts), Outlook/corporate, Toodledo and MobileMe. Everything does come together in my iPhone. The current solution involves a wide variety of vendors. For example, Apple's MobileMe calendaring is pathetic; far weaker than Google Calendar and a joke compared to Outlook (which makes Apple's no-show on tasks even more crazy). On the other hand Apple's Contact framework is very robust, much stronger than Google and a rival to Outlook.
This ruddy mess is a real indictment of Apple and a fat opportunity for the PalmPre.
So much for prelude. Here’s the outline, strictly for the uber-geek:
Here’s what I actually did:
- Copying contacts from Outlook/Exchange root to Outlook PST caused the EX (Exchange server x.500) email addresses to be updated to SMTP (standard internet) email addresses.
- PST on thumb drive to home (simple)
- Copy into Home Contacts
- Sync to MobileMe
- In MobileMe web assign all to a Group
- Sync to OS X Address Book (small conflicts)
- Sync to iPhone (ok)
- Sync to Outlook Home: Each Group in OS X Address Book became a Contacts Subfolder in Office 2003. This means the cardinality relationship to Address to Group may have to be One to One.
- Contact belongs to two Groups in OS X Address Book (multiple inheritance)
- Contact assigned to ONE Subfolder in Office 2003.
- In OS X change Group assignments.
- What happens in Outlook?
Here’s what I suggest doing (LOTS of backups of OS X Address Book as go along)
- Outlook/Corporate create PST file, copy work contacts. Do not copy lists or groups of contacts, only contacts.
- PST file to thumb drive
- Home Outlook mount PST data file. Make sure Contacts folder is empty
- Sync iPhone to OS X Address Book
- Create new group in OS X Address Book that will hold corporate contacts
- Sync to fresh MobileMe Account
- Sync fresh MobileMe account to home Outlook
- Now Outlook will have an empty subfolder. Dump the Contacts transported into the PST file into that empty folder.
- Sync from Outlook to MobileMe
- Sync from MobileMe to OS X Address Book
- Sync to iPhone
A partial index to past and related efforts at work/home Contact integration:
- Synchronization (all)
- MobileMe (all)
- Outlook (all)
- Contacts (all)
- Synchronization is Hell.
- Root causes: Why you can't sync your work and home calendars to your phone
- Project Contacts: Integration across iPhone, Google and whatever
- Work home contact integration: Outlook to Google to OS X Address Book (X.500 EX email problem)
- Synchronization case study: Address Book, the iPhone, and Google Contacts
- iPhone sync to Google contacts - 3 methods and work/home implications
- Outlook contacts to OS X Address Book - 3 techniques
- Google saves my iPhone (Google Exchange Server emulation for iPhone)
- Googaby: Novel approach to Google Contacts and OS X Address Book integration
- OS X Address Book to Google Apps Contacs using Google ActiveSync
- Work home contact integration: Outlook to Google to OS X Address Book
- Access OS X Address Book records using OpenOffice database?
- Synchronizing iPhone and Gmail contacts: getting OS X Address Book into Gmail
- gSyncit vs Google Calendar Sync with Outlook 2007
- gSyncit for Outlook 2007 to Google Calendar and Contacts Sync
- Prediction: We won’t see a fixed MobileMe until 10.6 is out
- MobileMe alternatives – including for iPhone Sync (MacWorld)
- Palm Pre is Exchange sync based
- iPhone: MobileMe vs. Google services
- MobileMe, Microsoft Outlook, Exchange, iTunes and yes, sync Hell
- Is it too late to go back to Palm 1994?
- Palm to iPhone - the update
- Synchronization is hard - more evidence
- Palm to iPhone migration - address book and notes
- Spanning Sync tells us what's wrong with Google's free CalDAV sync
- Apple can't do synchronization - again
- MobileMe syncs with Outlook (but then Apple turned it off for Exchange clients)
- Interoperability and my Contact information: Microsoft Outlook and Access, FileMaker Pro and Palm Contacts
It's weird how powerful MobileMe contacts are, yet how feeble MobileMe calendaring is. We're due for a MobileMe relauch, so I expect some developments before September.
Lastly, I should probably mention why I took this route. The more I looked at the workarounds for getting Outlook/Exchange corporate contact data to Google or the OS X Address Book the worse they looked. Their are problems with data models, problems with the intractable horror of the Outlook Add-In architecture, problems with Exchange server and problems with corporate access. This approach is crude, but for me, once I figure it out, fairly painless. I think it will fly until we get something better.
In the meantime, I'm rooting for the PalmPre to humiliate Apple and make them reconsider the direction they're taking.
Update 5/15/09b: Now that I've got this setup working I can see weird new affordances. For example, one of my top 10 OS X frustrations is the inability of FileMaker to work with the Address Book SQLite data stores. Ahh, but now my address data is synchronized between Outlook/Home and Address Book, and I can use Microsoft Access with Outlook/Home. So I can clean things up there, and MobileMe sync will propagate my fixes. I think I'll find a way now to get my Google Contacts into the battlefront.
Update 5/16/09: Great comment by Faheem, who's achieved a similar outcome using Plaxo without paying for MobileMe. I took a look, but Plaxo didn't feel right for me.