Free Tech Support: How can I sync my iPod with both Outlook and iCal?

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Today's question:

I have a Mac at home (iBook G4 running Tiger) and PC at work (Windows XP). Now that iTunes 5 supports syncing with Outlook, can I use my iPod to keep my iCal/Address Book synced with my Outlook calendar and contacts?"

While it's great that the iPod can now sync with both iCal and Outlook, dual-platform syncing isn't really what Apple had in mind with this. Additionally, according to posts on Apple's support boards, there are still a lot of bugs with this, and even Apple recommends the kludgey workaround of exporting your Outlook data to .ics and .vcs files if you have problems. Additionally, copying data from your iPod to your Mac or Windows PC isn't directly supported by Apple. Any data you have stored in your iPod will be overwritten by the current data from either your Mac or PC, not synced with it. That doesn't mean this is impossible; it just takes a little work. Read on for some answers...


First, you should probably forget about using the iPod itself as a go-between for the data. Instead, sync your data between your Mac and PC, and then export the data from there to your iPod. The easiest way to do this is to use a third-party program to sync iCal and Outlook via your company's Exchange server. Snerdware's GroupCal can sync just about anything Outlook can throw at it, including events, tasks and even meeting invites. The current version, 2.5 beta, is the first one to work with Tiger, and the company admits it's a little buggy, but it still may be your best bet. A separate product from the same company, AddressX, can sync the OSX Address Book with your Exchange Server's Global Address List. Of course, all this compatibility doesn't come cheap: AddressX is $19.95, and GroupCal is $54.95.

If you want a free solution, you can use a program like Outport or iAppoint to export your Outlook files into formats that iCal and other Mac programs can use. However, staying in sync like this will definitely require a bit of manual work. Of course, if you're really determined to use a pocket-sized device as your means of syncing, there is a way to do it: just ditch the iPod and get a PDA. You might have to pick up some extra software, but once you set it up properly, you'll have all your data in one place in your pocket —and you'll still be able to use it as a portable music player.

Tags: commercial, freeware, howtos, opensource