In brief:  I upgraded to iPhone Firmware 2.1, and my Microsoft Exchange integration broke.  I work at eBay, where we use Microsoft Exchange, Outlook and Web mail.  With my BlackBerry Pearl, everything just worked, without a thought.  With iPhone Firmware 2.0, 2.01 and 2.02, I was delighted that everything just worked too — a seamless transition from RIM, right?  Wrong!  With iPhone Firmware 2.1, email stopped arriving completely and all my contacts and calendar events were deleted from my iPhone and no longer syncing.

This was a disaster because of my setup.  I have a PC at work and a Mac at home, but I have (foolishly?) relied for the past 2 companies and 8 years entirely on my work Outlook to manage my calendar and contacts.  In other words, I have no other complete record of calendar events and contact information other than in Outlook.  With the Exchange integration broken, I now had an empty iPhone calendar and empty contacts.  Nothing, no ability even to call anyone without looking up their number in Outlook.  (No one memorizes numbers in this day and age, do they?)

Realizing this is a dangerous dependency, I recently had started to look to backup my data online.  First, I installed Yahoo! Autosync to sync Outlook with Yahoo! Address Book and Yahoo! Calendar.  This didn’t work very well.  I have close to 1000 contacts records in Outlook.  Inevitably, the number of contacts, in Yahoo! Address Book didn’t match the number in Outlook, Yahoo! Autosync failed to merge records for the same person, and, in many cases, critical information was missing.  Probably some sort of problem with field mapping.  Inelegant.

Second, I exported my Outlook contacts to a comma-delimited .csv file and then imported them into Gmail.  This had the same problem as Yahoo! Autosync — mismatched record counts, non-merged records and missing data.  I also tried Google Calendar sync to sync between Outlook and Gcal.  This worked fairly well but takes an inordinately long time to complete; I think the application starts afresh with every sync.

With broken Exchange integration and no clear solutions on Apple’s discussion boards, I now needed an alternative method to get calendar and contacts synced with my iPhone.

Here’s what I want:

• Ubiquitous access to email, contacts and calendar — from my work desktop, from my home desktop, from any Web terminal and from my mobile device . . . . For me, this means Outlook, Web mail, Gmail/Gcal, Yahoo mail/Address Book/Calendar, Mac Address Book/iCal and iPhone
• Uniform data — no duplication of entries, no omitted entries and consistent data across platforms
• Over-the-air sync — what good is a mobile device if I have to plug it in to get data on it?

Clearly, as much as Apple claims to be targeting enterprises with the iPhone, Apple isn’t ready.  They don’t even use Exchange at Apple is my understanding.  They don’t understand enterprise activation.  They don’t understand Enterprise-level support:  After several calls to Apple, their ultimate advice was:  We have no idea why Exchange broke, too bad, good luck.  Thankfully, email spontaneously restored after a couple of days, but I will no longer trust to the Exchange integration for my calendar and contacts, which remained broken last time I attempted to integrate.

Next post, the available options.