Since day one of owning my iPhone, I have had syncing issues with it. I first reported the issue on June 30th and to my amazement not a single other person seemed to have been experiencing long sync issues like I was. I’ve searched Apple’s support site and many other iPhone sites and I’ve never found anyone else having problems, save one. The one I did find had no response to their issue (I’ll have to go find that post and reply to it.) So, I just lived life with 30 minute sync times in awe of my other iPhone friends and their few minute sync times.

Well, things changed Sunday night. That’s the night I migrated from my existing Exchange server to my new Exchange 2007 server. Since the good folks at Redmond thought it wouldn’t be prudent to have a mailbox migration tool for my provider to just import my current mailbox, I had to drag folder tree by folder tree to my new Exchange server mailbox. With 700+ MB of messages and such, I knew this was going to take a while on my limited upload broadband connection and anything I could do to minimize the upload time, I was willing to do.

I put Entourage’s calendar into list view and waited a few minutes for the filter to do it’s stuff. When the count ticker finally quit its tabulation, it stopped at a large number. A very large number. 35,709. Yup, I had over 35,000 events in my calendar dating all the way back to 1998 and what I quickly noticed was a ton of duplicates, mainly of re-occuring events. When I saw this, I remembered how Entourage and its syncing with iCal created some duplicates way back in June. I guess it was more than just “some”.

After spending over an hour going through the long list of events and deleting globs of duplicates in the 221 count (what an odd amount of duplicates!), I finally was able to bring my event amount down to about 5,000. I then put the iPhone on its cradle and — BAM! — in two minutes the entire iPhone was synced. That was a 28 minute reduction! In fact, it happened so quickly, I thought maybe it timed out and performed the sync again and once again, two minutes. Wow, what a difference 30,000 less events make.

Needless to say, I’ll be closely monitoring my events and seeing if the iCal/Entourage sync service is duplicating items again. My suspicion is it will continue to do so and I’ll need to figure out what is causing it. I’m sure the next version of Entourage may correct this; however, with the updated mail.app and iCal coming this week in Leopard, I may just convert over to the Apple coded applications and say goodbye to Microsoft.

35,000 events. Amazing…