You see, in an attempt to squeeze every last dollar from the consuming public, Apple has handicapped the iPhone so it cannot handle synchronization from multiple calendars. To make matters worse, Apple has chosen not to release the calendar APIs to third party developers, which destroys any hope of a third party solution to calendar synchronization.
Apple’s attempts to justify this is nothing more than eyewash as it’s plainly clear to see this is nothing more than a marketing initiative, not a technical problem. Apple’s MobileMe service promises to synchronize all your calendars for a $99 annual fee. In other words, out of box iPhone calendar synchronization is possible, but it will cost you $99 to activate. How the consuming public puts up with this type of behavior still gets me. No thanks, Apple. I’ll figure out a way to do this on my own.

My work calendar is natively synchronized to the iPhone via its exchange synchronization. But I also have a personal calendar I use at home that I’d like to merge with my iPhone calendar.  Googling “iPhone multiple calendar synchronization “ returns a myriad of links regarding the problem, with very few solutions. The solutions I was able to find were rather hoaky or required syncing from a web service, such as Plaxo or Funambol. We’ll talk more about Funambol in a bit.

I realized fairly quickly that I needed to evaluate this problem from a different angle and then it hit me! Because the iPhone was already syncing with my work’s Exchange server, the simplest solution was to sync my work exchange calendar with my personal calendar. After a lot of reading and research I finally stumbled onto the underlying answer: SyncML. SyncML is a standard to sync PIM information between devices.

Here’s what you need to get it to work – or at least what I did:

• A home server with Internet access – I used my existing Gentoo Linux server.
• A groupware solution that supports SyncML – Since it had an existing package for my Linux distro,  I chose eGroupware as my server solution. Funambol is another good option since they make their server software available to download for free.
• A client that supports SyncML – I used the free Funambol client plug-in for Outlook.

After installing the Funambol client to all my outlook clients (work, home computer, personal laptop) I configured them to sync to my Gentoo server on a regular schedule over an encrypted SSL channel. End result? No matter which computer I’m using, my Outlook calendars are synced… and as an added bonus, so is my iPhone.