Like many people who have made the switch from a PC to a Mac, Joel Evans has learned how to manage a work-around or two. I read with some interest an article which he forwarded me this morning, because it details some of the frustrations I was experiencing when syncing my iPhone to Entourage. I was becoming increasingly frustrated because events that I’d enter into the iPhone would not transfer back to my MacBook, which was causing me to miss appointments (totally not cool!). It eventually got so bad that when I stopped using my Exchange account, I also abandoned Entourage and went to iCal, the native Mac calendar application. Looks like I wasn’t the only one…

Out of the box the iPhone is supposed to sync effortlessly with Entourage. While that’s the claim, in the past I’ve had more than my share of issues. Sometimes the syncing just doesn’t work, other times it syncs from the iPhone to Entourage but not back again. I’ve tried a number of “fixes” in the past and a couple of months ago I couldn’t take the strange behavior anymore so I moved to just iCal and left Entourage out of the equation.

I have been thinking about getting another Hosted Exchange account because I am about to start using a Windows Mobile device again, but the idea of how I would move all of my data back to Entourage was proving rather daunting; I didn’t see an easy way to do it. Luckily Joel also reached that point slightly ahead of me…

Last week I received a Blackjack II loaded with Windows Mobile 6.1. It was working great and since I pay for a hosted Exchange account, I figured it was time to finally figure out how to get Entourage to work in my world again. The reason? While syncing between iCal and iTunes was working fine, iCal doesn’t connect to my hosted Exchange account, so I needed to get Entourage and Exchange back in the mix.Here’s how I did it:

First off, the biggest problem I was encountering was the use of multiple calendars in iCal. This occurred because I had created a new calendar called “sync to iPhone” when I was having my issues. I had set iTunes to automatically save appointments created on the iPhone in that calendar, since I couldn’t get them into the Entourage calendar, which is created automatically when you enable Sync Services in Entourage (more on that later). The advantage to multiple calendars is that you can have separate work/home calendars, and keep all of the information separate on the calendar of your choosing. In iCal you can overlay them on top of each other, with different colors showing you which appointment goes with each. Entourage doesn’t offer this functionality, so you need to have a one-to-one calendar syncing relationship, which is why it creates the Entourage calendar in iCal by default.

I swear, it’s like Joel was sitting next to me, looking at the “mess” I have created on my desktop, when he wrote this tutorial. I’ll leave it to you to read how he resolved the issues, but if you are in the same boat – trying to get multiple calendars, multiple devices, multiple programs, multiple platforms and Exchange to play nicely together, Joel has proven himself to be a worthy mediator.

His note at the end is certainly worth pondering, too:

I have to wonder if Apple is going to make this a bit more seamless since the company licensed ActiveSync from Microsoft and plans to have it in iPhone 2.0 when it ships in June? Also, Apple is rumored to be rolling out push e-mail on .Mac next month, too, so who knows what will happen with Mail and iCal on Leopard by then? Until then, try syncing my way.

Link: Getting iCal, Entourage, Exchange and iTunes to play together nicely