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For six years, the Internet Nexus served as my technology blog, but I've since started blogging at the SuperSite Blog instead. If you're looking for the blog, please head there. --Paul



Tuesday, July 10, 2007

iPhone synching woes, Part 3

OK, the final round: This time, I tried syncing the iPhone with Outlook 2003 running on Windows XP with Service Pack 2 (SP2). As per the last installment, I did a clean install of XP with SP2, installed the 100+ post-SP2 critical and suggested fixes, installed Office (this time Office 2003), and configured Outlook with two local calendars, adding a single appointment to each for testing. (Outlook 2003 does not support subscribing to Internet-based calendars like Google Calendar, so I had to skip that for this test. See below for a workaround.) Then I installed the current version of iTunes, plugged in the iPhone, restored it, and set up syncing.

I got not love, sorry. As with previous attempts, iTunes refused to see that there were multiple calendars configured and grayed out the "Selected calendars" option, leaving just "All calendars," which isn't really "all calendars" at all, but is instead "the default local calendar only." After sync, I could see the appointment I made in this calendar, but not the one in the other local calendar. Game over.

I've now tried to make this work on two separate Windows versions and two separate Outlook versions. (And on the Mac, too, meaning I've tried virtually every supported combination of operating systems and calendars.) It's clear that, on Windows at least (Apple's biggest market), iPhone sync is horribly broken. Regardless of the supported Windows or Office version you use, the iPhone will only sync with the single default local calendar in Outlook, and not with any other calendars, be they local or Internet-based. This is a problem for a number of reasons, but the most damning is that calendar sync with multiple calendars (local, Internet, whatever) actually works fine with a normal iPod. Why it can't work with the iPhone--where, frankly, PIM sync is clearly more important--is unclear. And not to beat this to death, but seriously, Apple, could you support something other than Outlook? How about Windows Calendar? Google Calendar? Something.

With that horror show out of the way, I turned my attention to actually syncing Google Calendar with the iPhone. To make this work, you need to use a third-party tool that syncs Google Calendar with Outlook; I use SyncMyCal for this purpose and it works wonderfully, even the free version (which requires manual syncing). After installing SyncMyCal, I configured it to sync into the default local calendar in Outlook 2007, plugged in the iPhone, restored it, and synced it up ... again.

This time, success. And it only took five iPhone restores over two OSes, two versions of Office, and three different PCs (and a Mac, just for testing). Oh, and a third party sync application that, unlike iTunes, actually works. It's amazing how satisfying "it just works" can be when it actually does work.

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