Friday, May 15, 2009

Project Contacts: Now mixing Outlook/Exchange, PST file, Outlook/Home, MobileMe Sync, OS X Address Book and the iPhone.

A recent Apple Discussion Thread led me to take a new direction with Project Contacts.

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.

Expected problem:

  • 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)

  1. Outlook/Corporate create PST file, copy work contacts. Do not copy lists or groups of contacts, only contacts.
  2. PST file to thumb drive
  3. Home Outlook mount PST data file. Make sure Contacts folder is empty
  4. Sync iPhone to OS X Address Book
  5. Create new group in OS X Address Book that will hold corporate contacts
  6. Sync to fresh MobileMe Account
  7. Sync fresh MobileMe account to home Outlook
  8. Now Outlook will have an empty subfolder. Dump the Contacts transported into the PST file into that empty folder.
  9. Sync from Outlook to MobileMe
  10. Sync from MobileMe to OS X Address Book
  11. Sync to iPhone

A partial index to past and related efforts at work/home Contact integration:

Update 5/15/09: Now that I've got this working I'm trying various optimizations. For example, my contacts don't change that often. It's easy to create a view in Outlook that sorts by modified date. It's fairly trivial to send out a few changed .msg in an email and let Outlook at home merge them in. I still have to think about how to work with Google's Contacts, but I'm seeing a few interesting options.

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.


jetlagged said...

John, have you looked at Plaxo? I use Plaxo to sync Outlook contacts at work with Address Book contacts at home, and it works a treat. I can edit a contact on either side, or even online via Plaxo's website, and the changes are immediately reflected in Outlook, on my BlackBerry, my iPhone, and on the iMac. I love it!

I don't sync with Google Contacts because their implementation is such a mess, though recent changes by Google are encouraging (specifically, the fact the Google is now pushing Contacts as a stand-alone module).

I also use Plaxo to sync my Calendar across both machines, but the setup here is slightly different. I prefer the way iCal handles multiple calendars, and use it to subscribe to public and shared calendars. These are synced with Google Calendar directly via the iPhone.

But only one calendar is synced to my work laptop (Windows/Outlook) via Plaxo, and I try to avoid making edits on the iMac because most entries involve multiple people in multiple timezones, and the way Outlook handles multi-day events and/or recurring events is quite different from everybody else.

Anyway, in case you haven't already tried Plaxo, do give it a shot:

You might be surprised.

JGF said...

I really do need to look at Plaxo. I've been hoping to avoid them because the last I looked I didn't care for their business model.

You clearly know what you're talking about though, so I'm impressed. I'll definitely investigate.

When you sync with Plaxo do you end up with your personal contacts on your corporate outlook? I have tried to avoid that in the past, but really it's not a big deal for me.

I also like that you've been able to sync just one calendar from work to Plaxo and yet use multiple calendar with iCal and gCal and your iPhone. That's also what I do.

Lastly, a single source for both Work Calendar and Contact sync is an improvement.

Like you I devoutly hope Google beefs up their Contact management. It's clearly strategic for them, so it's puzzling how badly they've floundered. Maybe they need to find some old Palm, Outlook or Apple Address Book veterans to advise them.

Oh well, we do have lots of evidence that Google is as human as the rest of us!

jetlagged said...

Yep, I sync all contacts to all machines and devices. This is good enough -- I used to use categories to group and filter contacts, but increasingly find myself using a simple search now.

And I fully understand your apprehension about using Plaxo. They had a rather obnoxious privacy policy a few years ago, but they learned their lesson the hard way and came back with one of the tightest privacy policies around. It helps that their sync technology is so damn good.

Like you, I've tried almost everything in my journey from Palm to Outlook to Blackberry to iPhone to "cloud", and while this isn't perfect it is the closest I have come to keeping things in sync.

Oh, and FYI I just ignore their attempts at becoming sticky by building a social network. More and more of my contacts are starting to explore those features now, but most of them (myself included) have just linked an existing status feed so it's hardly what one would call sticky. What IS sticky is their fantastic address book -- you can choose which contacts see what details, and you can also choose what updates from your contacts you want to incorporate into your own contact record for them. This is fantastic.

One shortcoming is their inability to sync Smart Groups from the Mac OS X Address Book, but I'm starting to suspect that this is a Mac restriction. I'm a big fan of Smart Folders of all sorts, from Smart Playlists in iTunes to Smart Albums in iPhoto to Smart Groups in Address Book, but none of them sync to anything else (e.g., there's no way to use Live Sync to replicate Smart Albums to DropBox, or Smart Playlists to my DLNA server). But that's a topic for another day...

JGF said...

We are kindred spirits on this front -- no doubt! Do you have a blog of your own? I didn't see one on your blogger profile.