iPhone sync problems with Entourage 2008

Wouldn’t it be great to sync the contacts and events on your iPhone with Entourage on your laptop? Yeah, it would – if it worked. But, having exhausted the best minds at Apple and Microsoft in trying to find a solution, my recommendation is give Entourage the flick, and use Mail, iCal and Address Book.

“By this time, I’d had a complete gutful. I’d lost probably 3 days work – not to mention my tether.”

Know how to sync the iPhone with Entourage? Where you were you when I needed you?

An enforced iPhone 3G early adopter

I wasn’t going to be an iPhone 3G early adopter. Let the bugs get sorted out, then make the shift was my grand plan. But, then my old Sony Ericsson refused to charge any more and it was a mad dash to get the old data onto an iPhone before its predecessor kicked the bucket.

First impressions blighted by poor battery

There wasn’t much of a honeymoon. I’m not a big phone user, but even without using the iPhone as an iPod, browser, photo album or GPS, I was needing to charge every day. If you’re a serious business phone user, the iPhone is not yet for you.

Vanishing iPhone contacts

The iPhone didn’t synch with my Entourage initially but I was too busy to worry about it. However, matters reached a head when all contacts on my iPhone vanished. Gone. Not a trace. Not once. But twice.

Apple says Microsoft is causing synch problem

I went into the Genius Bar at Apple in George St, Sydney, and Alex, a nice young lad with curly black hair, was very patient but unable to solve the problem. He said he thought the problem was with my Microsoft Office.

Microsoft says I should reinstall Office 2008

So I get on the phone to Microsoft Support, and they run me through a few things. But after an hour or two, they have no more clues and suggest that I reinstall Microsoft Office 2008. Easy for you, I say.

Reinstall of Microsoft Office 2008 doesn’t fix synching problem

But I do as I’m told. I reinstall Microsoft Office 2008 – an exhaustive process since it involves downloading 5 separate subsequent and sizable updates. And then re-entering all your email accounts. And I have a lot of email accounts. Does the reinstall help? Not one bit.

Reset Sync history, they say

I get onto Apple Support again, and a pretty obvious solution is suggested. Reset the Sync History in iSync, they say. No skin off my nose. So I do. Does it help? Not a jot.

Reinstall of Mac OSX fixes syncing problem – for about 5 minutes

I call Apple Support. They run through a bunch of things, but none of them work, so after an hour, they say the only solution is to reinstall my Mac OSX from the install disks. And then all the updates. Sure, what the hell? What’s another lost half day by this time. So I do it. Does it help? Well, initially, yes.

Vanishing Contacts, Emails, Events

It all looked fab. The iPhone synched with Entourage 2008 on my G4 PowerBook and I thought the battle was won. But then I shut the laptop down and restarted, and everything was gone again. And I mean everything. Emails, events and contacts were gone not just from my Entourage, but also from iCal, Address Book and Mail. And off Mobileme. I’m weeping by this point.

Restore the iPhone, they say

I’d been having problems for more than a week, so I’m a little surprised when someone suggests a fairly obvious solution. Restore the iPhone. So I do. And the iPhone syncs with Powerbook. But then, when I make a change in one, it doesn’t show up on the other when I sync again.

“Synching problems between Entourage and Sync Services well known”

What was particularly galling was that everyone at Apple and Microsoft were acting like my situation was completely unusual. That they’d never seen anything like it. And, yet, when I did a Google search, I found lots of people having the same problem. In fact, I found one who said that “the synching problems between Microsoft Office 2008 and Apple’s Sync services are well known”. To everyone but Apple and Microsoft apparently.

Farewell Entourage

By this time, I’d had a complete gutful. I’d lost probably 3 days work – not to mention my tether. I’d been to the Genius Bar twice, I’d had about 5 lengthy sessions on the phone to Apple Support, and another one with Microsoft. Nothing had helped, and no-one took responsibility for fixing the problem. Life is too short. I gave Entourage the arse, and switched back to using Mail, iCal and Address Book.

My life is now blissfully in sync

And, as they say in the cheesy shampoo commercials, am I glad I did. As soon as they were set up, my iPhone synced first time. Events, Contacts and Mail were as they should be. It then synched with Mobileme. There they all were – admittedly they were all a day early – but I soon fixed that by setting the Time Zone. So my recommendation is clear: if you are a Mac user and an iPhone user, do not bother trying to sync using Entourage. Use the separate Apple Mail, iCal and Address Book programs and, who knows, your mobile phone and laptop might actually revert to being productivity tools rather than resource blackholes.

Know how to fix the iPhone – Entourage syncing problem?

So you know how to fix the iPhone / Entourage synching problem? Well, that’s great. To spare others the pain I went through, please share your knowledge with the support staff at Apple and Microsoft. But the horse has bolted for me. My Entourage days are over. But, now I must go. My iPhone has just reminded me – and my synched PowerBook has as well – that I need to be somewhere. Here’s hoping you find synching your life a whole lot easier than I did.