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 websites. 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.
It turns out that syncing your Google calendar and your iPhone works really well and is more or less goof proof. And once those two are in sync, 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 sync 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 sync 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 sync with it, and the reminders don't go away until you open Outlook and check "dismiss." Kind of annoying, but not a big deal.
Syncing Outlook contacts without using iTunes is, alas, only possible for consumers who subscribe to Apple's MobileMe. That would be okay if it were free, but it isn't. MobileMe, costs $99 a year and has been plagued with intermittent outages. Business customers, whose companies use the premium edition of Google Apps, can sync contacts with Outlook.
Fix your iPhone vs Outlook contacts mess
I'm not a programmer, so maybe there's some arcane reason that Outlook can't sync with Google Contacts. But I suspect there's a more mercenary explanation. Why give away functionality when you can sell it? I can't prove that, but I bet it's the case and it ticks me off.
My suggestion: move your Outlook contacts to Google Contacts, and then sync with your iPhone. Having said that, I think Microsoft's Outlook is a more powerful contact manager than Google's. But given the increasing importance of mobility to many of us, it's a reasonable tradeoff.
Begin by exporting your Outlook contacts as a csv file. Then import that file. Here's a link to a Google help page that explains some of the fine points. Note that the instructions are for importing into Gmail, but the procedure for importing into Contacts is identical.
To get those contacts onto your iPhone you'll need to spend $4.99 to buy an app with the silly name of SyncInaBlink. Don't be put off. SyncInaBlink works really well, merging iPhone contacts and Google Contacts in, well, a blink. Actually, the first time you use it the sync will take a while if you have a lot of contacts, but after that it's really fast and happens over the air. I've been using it for about a month and have yet to encounter a significant glitch. I'm unclear on when the latest version was released, but I'm running iPhone 4 and it works just fine.