MobileMe, Microsoft Outlook, Exchange, iTunes and yes, sync Hell

I thought I might finally have a use for MobileMe. I thought I might be able to use it to get some calendar information from work Outlook/Exchange to MobileMe to iCal to my iPhone.

Hah.

You know how this goes. With the last release of MobileMe for Windows Apple disabled calendar synchronization when Exchange is in the mix:

MobileMe Control Panel: Calendars is dimmed, cannot be selected for syncing in Windows:

.... Outlook is installed but connected to a Microsoft Exchange Server, and MobileMe Control Panel 1.2 or later is installed. If Outlook is connected to Exchange, Calendar syncing with MobileMe is not available. For more information about MobileMe and Exchange syncing, see this article...

There's no explanation of why this was disabled in MobileMe 1.2, but I suspect bidirectional MobileMe sync was trashing Exchange calendars [1]. We've heard rumor that Apple is having a dreadful time getting Exchange support working with 10.6; so it's not surprising that a sync setup involving Exchange 2003/2007 <-> Outlook 2003/2007 <-> MobileMe might be umm ... problematic.

Apple should have expected that; synchronization is Hell.

Most confusingly (yes, synchronization is Hell) Apple claims that Contact sync is also forbidden when MobileMe is involved...

MobileMe Control Panel for Windows 1.2 or later will automatically turn off syncing with Outlook for you if you had it setup previously. This text appear when it detects that you are using Outlook with an Exchange Server:

"Syncing of contacts and calendars with Microsoft Outlook is not available while Microsoft Outlook is configured to use Microsoft Exchange Server. You may still directly access your data from Exchange over the air using your iPhone or iPod touch."

You will still be able to sync your contacts with Windows Contacts (on Windows Vista) or Windows Address Book (on Windows XP), as well as with Yahoo or Google contacts, per usual.

When I looked I saw that Contacts sync was not grayed out, but maybe that's sync to Windows Address Book (which should be empty though there's a possibility of some brain blowing reflection from Outlook Contacts).

Apple's kb article mentions using Exchange ActiveSync to get Exchange data on the iPhone, but that's a diabolical trick. We already know that will wipe all personal data from the iPhone -- unless you sync personal data from OS X to MobileMe and MobileMe data to the iPhone.

If your head isn't exploding you're not paying attention. Did I mention synchronization is hell?

Ok, but what about the old iPod-style iPhone Calendar synchronization via iTunes and a USB cable? (Taking MobileMe out of the picture entirely, in case you missed that) ...

... If you are not able to use Exchange ActiveSync, but would like to sync your Outlook data to your iPhone/iPod touch while using Exchange, you can sync your iPhone/iPod touch through iTunes over a USB cable. Note that if you sync an iPhone/iPod touch this way, you will not be able to sync your iPhone/iPod touch over-the-air with MobileMe.

You see, you can sync an iPhone with one of:

1. iTunes to Outlook (w/ or w/o Exchange) via USB cable (then Outlook cannot sync to MobileMe)
2. iTunes to iCal which can in turn sync to MobileMe (OS X only) via USB cable
   
3. MobileMe
4. Exchange Server via ActiveSync
5. MobileMe and Exchange Server via ActiveSync
   

But what about synching one iPhone to iTunes to iCal at home and iTunes to Outlook at work via the USB cable? Although one person reported a solution using Entourage, I'll stick with my understanding that this is strictly impossible.

Which leaves Outlook to Google calendar to Missing Sync to iCal to iPhone via USB cable at home. (Don't even think of making this anything but unidirectional.)

If you understood that last sentence, I'm afraid of you now. If your head just exploded please join the club.

I wonder how things work with the gPhone (Google Android)?

[1] I'm not insane. I would never enable bidirectional sync in this setting, I was looking for unidirectional sync. I imagine Apple felt it would be tacky.

Update 11/3/08: The last option worked.