A colleague, Ryan Kaplan, sent me the following Entourage > iPhone syncing tip. Anyone else experienced this problem?
I was having a heck of a time syncing my iPhone with Microsoft Entourage. Every time I would try to sync, it would stall. I called Apple technical support several times and was unable to determine the problem. The indicated that because my iCal and Address Book were syncing fine, they were unable to support problems with a 3rd party, in this case, Microsoft Office.
I was frustrated because Microsoft and Apple have been collaborating for decades and they should be able to get their syncronizing working. After all, it's 2008. I remember having problems with my Palm III ten years ago thinking to myself that in 10 years, all of these stupid syncing problems would be resolved, but they haven't.
The problem is that I have 1,800 contacts in Entourage and they are syncing fine with Address Book. My calendar is also syncing with iCal. I would try to sync my contacts and calendar events with iPhone and it seemed to take forever, but never finished.
At one point, I left the syncing on all night to no avail. I tried many permutations of troubleshooting techniques and miraculously, found a solution. In order for me to sync correctly, I can only sync one segment at a time. If I sync my contacts, it takes 10 minutes. Then I uncheck the contacts in iTunes, and check the calendar and sync that independently. That only takes five minutes. It's not too tedious, but it works. I hope this helps someone out there.
Update: Problems syncing iPhone, iTunes and Office 2008 Resolved!
I’m running Office 2008 12.1.1 on top of Mac OS 10.4.11 (Tiger) and interacting with iPhone 2.1 5F136. I am not using MobileMe and I am not using Exchange (our office has Exchange Server 2000 and we aren’t upgrading anytime soon to 2003).
Instead, I am using Microsoft Entourage: Preferences: Sync Services to synchronize my contacts & calendar events with Apple iCal and Apple Address Book. The Sync Services are very reliable and work great.
The breakdown occurred when I used Apple iTunes to synch with Apple iCal and Apple Address Book. I could not synchronize everything all at once. I had to isolate syncing Address Book and iCal independently to get the synching to run successfully.
I called AppleCare and we created a new login user on my computer, and tested iTunes/iPhone syncing interaction with Address Book and iCal. Everything worked fine. They did not want to troubleshoot my Entourage problems b/c it’s a 3rd party, but they did try to help for about 5 minutes before saying that they think this is a known problem, but that they couldn’t provide support to fix the problem.
Then I got in touch with experts at Microsoft and their marketing team, they realized that I wasn't using the latest updates on Office. I’m so embarrassed that I didn’t try updating Office beforehand but it worked! I must have inadvertently turned off auto update checking on Office. So I updated to 12.1.3 and ran the sync through iTunes and it worked great. Then I updated to 12.1.4 and re-ran the sync and it worked again, like a charm.