September 15, 2010, 8:54 PM — Like many of you, I've had trouble syncing Outlook calendars and contacts with my iPhone. After more than a year of syncing without much trouble, it suddenly stopped working. I've spent a lot of frustrating time tweaking this and that and talking with Apple support, but to no avail.
Naturally, I looked for solutions on Apple support forums and all sorts of techie Web sites. I noticed that many people have had this problem over the years with different versions of the iPhone and different versions of Outlook. There are all sorts of solutions. Some of them work, some of them don't. In general, it's a real pain. But I finally discovered a workaround.
[ What do toilets, beer and elevators have in common? They all send many iPhones to their death. See 5 Strange Ways iPhones Die: Insurer Hears it All. ]
It turns out that synching your Google calendar and your iPhone works really well and is more or less goof proof. And once those two are in synch, if you still want appointments to show up in Outlook, it's easy. Yes, you've added a step, but as I said, it's a workaround. And best of all it doesn't involve the tricky interplay of iTunes and Windows, which appears to be the source of many of the problems.
Fix Your iPhone Calendar Mess
Here's how to synch Google calendars with an iPhone:
1. On your iPhone, go to Settings > Mail, Contacts, Calendars > Add Account > Other > Add CalDAV Account
2. For the CalDAV settings, fill out the form, which asks for the server (www.Google.com) user name (Gmail address) and Gmail password. Tap next and that's it.
The synch is two way and happens over the air, so your phone has to be connected to the Web via WiFi or 3G. There's a brief lag, but not enough to be annoying. Remember to download Google Gears so you can work with the calendar offline.
Now to Outlook. First be sure you're not running a version earlier than 2003. Rather than go through all the steps, I'll direct you to the Google page that explains it clearly. In essence, you download a small application that syncs the calendars on a schedule that you set. The only glitch I've discovered has to do with reminders. If Outlook isn't running, Google calendar keeps trying to synch with it, and the reminders don't go away until you open Outlook and check "dismiss." Kind of annoying, but not a big deal.