The iPhone and Exchange

With all the hype surrounding the iPhone, I thought I'd stick my oar in the water and talk about what the iPhone means for Exchange Server administrators.

Over the last couple of years, I've chronicled my experiences with various Windows Mobile devices, including the Palm Treo 700w. Despite its flaws (such as not having nearly enough RAM), I've come to depend on the Treo to help me stay organized and in touch when I'm traveling or otherwise out of the office. Judging by the number of Windows Mobile devices I see at airports, hotels, and other places where business travelers congregate, I'm not alone.

Now, along comes the iPhone, an incredibly attractive device with a beautiful, fluid, smooth UI that makes Windows Mobile, Palm OS, and Symbian OS look clunky and antiquated by comparison. It has a ton of nifty consumer-level features; it includes full iPod functionality, a very capable Web browser, and full WiFi connectivity. On the other hand, it's missing some key features that business users have come to expect and demand:

• The iPhone doesn't have a physical keyboard. This is a deal-killer for many BlackBerry and Windows Mobile users. Apple's keyboard software is supposed to do a good job of making the onscreen keyboard usable, but I haven't used it enough to form my own opinion.
• The iPhone lacks several data types that are broadly supported on other devices. For example, the device has no task functionality, and you can't export notes from the iPhone to your desktop computer.
• There's no supported way for third-party developers to write applications that run natively on the iPhone, although Web-based applications work.

You might already have heard that the iPhone doesn't natively support over-the-air synchronization with an Exchange server. It supports IMAP; there's an "Exchange" account type on the iPhone that, when selected during setup, tells you that IMAP must be enabled on your Exchange server. The Safari Web browser properly checks certificates, but the Mail application doesn't. This circumstance eliminates one major annoyance of deploying Windows Mobile devices: the hassle of getting self-signed certificates onto a new phone. Of course, it also means that the Mail application can be fooled by a man-in-the-middle Secure Sockets Layer (SSL) attack, but that's a topic for another column.

Rumors have been circulating for a while that Apple has licensed the Exchange ActiveSync (EAS) protocol from Microsoft. I spoke with members of Microsoft's PR team, and they pointed out two salient facts. First, Microsoft doesn't comment on rumors (big surprise there). Second, Microsoft has licensed EAS to a number of other device vendors that compete with Windows Mobile. Because third parties can't add their own software to the device, any EAS support will have to come from Apple, and they're notoriously tight-lipped about product plans. For now, you're stuck using IMAP. It will be interesting to see what Apple's software upgrade path looks like for the iPhone, and how it compares to the way software updates work in the Windows Mobile, Palm OS, and Symbian worlds.