If someone asked you to think of a logical pairing of a computer and a cell phone, Apple's Macintosh and Microsoft's Windows Mobile is probably not the first one you'd come up with. Many Mac users gravitated to Palm OS-based devices over the past decade, especially for the intuitive, flexible PIM application Palm has had almost since day one (way before Apple's iLife suite, in fact). But what if you're stuck with a Windows Mobile handheld from work? Or better yet, what if you've got your eye on one of the ultrathin smart devices from Motorola, T-Mobile, or Samsung? Will it even work with your Macintosh? Mark/Space has your answer in The Missing Sync for Windows Mobile 3.0, and as my testing bore out, it's a winner.

The Missing Sync for Windows Mobile 3.0 is a universal application that works on both Intel and PowerPC-based Macs. Although I tested Mark/Space's Windows Mobile product, Mark/Space also sells versions of The Missing Sync for Palm OS smartphones and Sony PSP gaming handhelds. There's even a BlackBerry version in the works, though you can also use PocketMac's various BlackBerry applications if you have one of RIM's devices.

I tested the latest version of Missing Sync for Windows Mobile, version 3.0, which lets you sync photo albums from iPhoto, iTunes playlists (including podcasts), and files and folders, so you can work on documents once you leave the office. As Mark/Space helpfully points out, the program is intelligent enough not to copy any music over that the Q can't play, namely protected AAC files purchased from the iTunes Store.

Minimum requirements include 78MB of free space on your Macintosh computer, and you must perform a reboot after installation. The first time I fired up the program, it asked for some registration information and a registration code. Following the instructions, I went to Start -> ActiveSync from my test Motorola Q smartphone's menu and added a new Bluetooth connection. The Q found my test iMac Core 2 Duo (complete with internal Bluetooth 2.0) and linked up on the first try. Ever sync your handheld via Bluetooth instead of a messy USB cable? Trust me, it's hard to go back.

Once you're hooked up, you can initiate a new connection by going back into ActiveSync in the Q's Start Menu and selecting Connect Via Bluetooth. Sync-up was, at about 20 seconds, a little slow. Here's a beautiful thing—even though my Q is normally configured to talk with Microsoft Outlook on a PC, The Missing Sync was able to pull in a database of 451 contacts from the Q onto the iMac. It also transferred some contacts I had created in the iMac's Address Book back to the Q in the same pass. The program hit all the major data points, including addresses, phone numbers, e-mail addresses, and notes where applicable. I tried numerous additional syncs with new information in both directions, all of which worked without a hitch.

I spent some time poking and prodding The Missing Sync but couldn't trip it up. I was able to open JPEGs, PDFs, and even MPEG movies straight from the Q and play them on the iMac, and I could copy files back and forth without any trouble. Each time The Missing Sync saw new data on my handheld, it first asked me if I wanted to erase the Q or merge the data, and then asked again if I wanted to allow changes to the iMac's database.

The software also lets you install Windows Mobile .CAB files. This way you can buy software for your Windows Mobile handheld online, download it to your Mac, and then install it without a problem. The Missing Sync also works with Apple Sync Services, so that applications such as Microsoft Entourage 2004 and Chronos SOHO Organizer can synchronize properly with your handheld. Other nice features include how The Missing Sync shows a battery meter for your handheld, syncs Safari bookmarks with Internet Explorer Mobile, and can back up and restore your device's My Documents folder.

In short, The Missing Sync for Windows Mobile 3.0.1 is a powerful and flexible way to link up Windows Mobile handhelds to your Macintosh.