Executive Summary: The Apple iPhone scores with push email but behaves poorly offline and neglects the proper Exchange ActiveSync (EAS) verbs. It lets you create multiple IMAP and POP email accounts but offers just one Microsoft Exchange Server account per device.

When Apple launched the iPhone in June 2007, the company immediately grabbed an immense amount of mindshare. However, the first iPhone, cool as it was, wasn’t a very good email client. It didn’t sync with Microsoft Exchange Server, lacked a VPN client, and couldn’t run third-party programs. Here, I review the iPhone 3G, focusing on how well it works as a mobile email device compared with Windows Mobile 6.1. For my tests, I used the iPhone 2.1 software update, released in September 2008.

Basic Email Functionality
Let’s start with email. Apple got the single biggest item right: Push email works properly. Mail arrives when it’s supposed to, and you can send replies the way you’re supposed to. As you can see in the sample iPhone email page in Figure 1, HTML mail displays beautifully.

That said, several rough spots exist in Apple’s implementation. The most noticeable one is the poor behavior of the iPhone client when you’re offline. Any attempt you make to move or delete messages when the device isn’t connected via WiFi or cellular means results in an error dialog box displaying. Another shortcoming is that the iPhone client expands every folder in your mailbox when you navigate between folders or accounts, making it needlessly difficult to move directly to an individual folder.

Additionally, Apple isn’t using the proper Exchange ActiveSync (EAS) verbs for message replies and forwards. EAS “smart reply” and “smart forward” verbs let applications tell the server to include the relevant message text, and the verbs also update the read/forwarded status so that other clients reflect the actions taken.

You can’t flag or unflag messages for follow-up or set out-of-office messages or timings with the iPhone, as you can do with Windows Mobile 6. In addition, the iPhone 3G frequently complains if you try to throw away a message that a client- or server-side junk filter has already moved elsewhere.

Calendaring
Disappointingly, the iPhone’s calendar functionality is probably the weakest part of its Exchange support. The iPhone can accept and act only on invitations from other users on the same Exchange server. The calendar software lets you create new meetings on your own calendar, but you cannot invite others. The iPhone limits recurrence patterns to daily, weekly, biweekly, monthly, and yearly appointments (no more first- Thursday-of-every-month designations). You can’t see or set the time zone for meetings, and there’s no way to find free/busy times or suggested meeting times. Windows Mobile 6.1’s calendaring functionality is far superior.

Tasks
The iPhone doesn’t include a built-in tasks/ to-do application. Apple missed the boat here, as this is a natural piece of functionality for a mobile device. In fact, there are dozens of such applications in Apple’s iPhone App Store.

iPhone 3G PROS: Superb interface; packed with features; supports Exchange ActiveSync (EAS); easy to operate CONS: Requires expensive data plans; offers poor calendar support; lacks a physical keyboard RATING: 3 out of 5 PRICE: Monthly service plus $299 for 16GB model and $199 for 8GB model RECOMMENDATION: The iPhone is a slick, beautifully realized smartphone that provides an unparalleled Internet-browsing experience. Its EAS support is a good start but is weak compared with the latest crop of Windows Mobile devices. CONTACT: Apple • www.apple.com • 408-996-1010

Policy Control and Security
Apple has implemented only some parts of the EAS protocol. In the security realm, this means that iPhones will honor the password-related policies you set for EAS devices. However, the iPhone doesn’t recognize the expanded policies introduced with Exchange Server 2007 SP1, and it won’t work with Microsoft System Center Mobile Device Manager 2008 because the iPhone can’t run the necessary client software. Windows Mobile devices warn you the first time you sync with a server that enforces a policy. The iPhone doesn’t do this, so if you accept the policy, you’re stuck with it. As a further annoyance, if you send a remote wipe request to the iPhone, the device will take more than two hours to finish it.

Not Quite the Right Stuff
The iPhone does many things right: It has terrific fit and finish, the web browser is better than anything available on any other mobile device platform, and the UI is polished, fast, and easy to learn. Unfortunately, the iPhone just isn’t up to par as a mobile enterprise email device. Windows Mobile 6.1’s maturity gives it a clear edge in this