PocketMac Pro 2.0

The biggest disadvantage of being a Mac person with a PocketPC is all the static you get from some of your Mac kin. But catcalls of “Quisling! Apostate! Traitor!” are quickly silenced by a quick demo of the hardware and software. Palm OS-based handhelds are for people who want to carry something more powerful than a personal organizer; PDAs running Microsoft’s PocketPC OS are for folks who want something smaller than a laptop — they’re the next-best thing to a Newton, right down to the built-in handwriting recognition.

What’s the second-biggest disadvantage? Well, Microsoft has no plans to release a Mac edition of its desktop software. There are ways around that — many PocketPC PDAs will work with VirtualPC — but simple, one-button syncing just wasn’t possible until Information Appliance Associates’ PocketMac Pro 2.0 came along.

Given that PocketMac is the only such solution — for now, anyway — how well it works might be secondary to the fact that it works at all. With this software, you can sync contacts and appointments between the PocketPC and either Entourage or your Mac’s built-in iCal and Address Book apps. You can move files (such as Word documents, MP3s, and photos) back and forth. You can install third-party apps on your PocketPC to expand its capabilities beyond its built-in Office suite, browser, and e-mail client.

The only important feature that PocketMac omits is the ability to synchronize your PocketPC’s mailbox and Internet Explorer bookmarks with their counterparts on your Mac. All Palm OS power users know how neat it is to be able to leave the house with a PDA full of unread e-mail, compose replies on the subway, and send them automatically by placing the device in its cradle; they’ll miss that if they’re using PocketMac on their PocketPC. And while Pocket Explorer is a tremendously powerful PDA browser, entering URLs manually is tremendously clumsy.

Installing PocketMac can be a serious trial. We tried it with three different Macs (an 800MHz dual-processor G4 tower, an 867MHz Titanium PowerBook, and a fresh-from-the-carton 12-inch 867MHz PowerBook) and three different PocketPCs (a Toshiba e740, a Hewlett-Packard Jornada 565, and a Siemens SX56 PDA phone). Getting the 12-inch PowerBook to work with the Jornada was straightforward, but the other installations were epic passion plays. For example, PocketMac couldn’t “see” one PDA, even though it was sitting contentedly in its cradle and plugged into the Mac’s USB port. Or the application could see the connected PDA and get it to start a sync, but then PocketMac would get hung up midway, requiring a force-quit. Once, placing the Siemens in its cradle caused an immediate system crash. PocketMac’s documentation trivializes the installation process, and the app itself neither keeps the user informed of trouble nor offers a gracious way to abort when things go wacky.

Even when PocketMac has been installed properly, rough edges show. Several times over the course of testing, the program “lost” the e740 on the USB port and could find it again only after a system restart.

Despite the exasperating installation and less-than-exhaustive documentation, Information Appliance Associates’ tech support is adequate, if not superlative. And PocketMac is indeed a functioning commercial application.

Macworld’s Buying Advice

PocketMac may be a flawed app, but for now, it’s the only game in town. If you’re in love with the huge power of PocketPC hardware and software, it’s worth the hassle. If not, you’re better off with a Mac-compatible Palm — or waiting for another company to step up with a PocketPC-to-Mac utility.