The iPhone is a sleek, sexy device that permanently changes our expectations for handheld devices. After holding an iPhone, it’s hard to pick up another cell phone and PDA without feeling a bit of a letdown.

The iPhone has a few shortcomings that are not immediately apparent when you look at one for the first time. Here’s a list of the big and small issues that users are discovering about the current iPhone. The most significant problem is Apple’s deal tying the iPhone to AT&T. Perhaps that was important to finance the deal or Apple thought it was necessary for marketing, but it’s a shame – AT&T is a horrible company to do business with and has a much weaker network than the competitors.

Let’s say you can swallow signing up for an account with AT&T. At the moment, the iPhone is not the right choice for Outlook users hoping to sync e-mail, calendar, and contacts to the iPhone. That’s especially true for businesses running Exchange Server, the software powering the mail system in Small Business Server 2003. Many reports online say that the iPhone is difficult to set up with Exchange Server – possible, but difficult to configure. Worse, even when it’s set up correctly, I’ve seen too many reports that it just doesn’t work very well.

Theoretically mail can be sent to the iPhone if support for IMAP is turned on in Exchange Server. That’s a protocol for retrieving mail, similar in concept to POP3 but seldom used until recently. Researching how to do that turns up warnings like this:

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imageAs I understand it, the iPhone can be set up to receive e-mail from an Exchange Server – but that’s it for over-the-air syncing. No contacts, no calendar sync over the air. Calendar and contact syncing is not done directly with Outlook even when the iPhone is in the cradle, if I understand right – first, Outlook has to sync with iTunes, then iTunes syncs with the iPhone. It’s a messy process that’s fraught with error.

It’s unclear whether mail sent from the iPhone ends up going thru the Exchange Server and showing up in Outlook Sent Items – I think not but I haven’t confirmed it yet.

This is likely to change soon, possibly in the next month or two. Two weeks ago Apple posted this job opening for a QA engineer:

The iPhone Quality team is looking for a motivated, highly-technical Exchange test/sync engineer with excellent problem solving and communication skills. You will join a dynamic team responsible for qualifying the latest iPhone products. Your focus will be testing Exchange and Outlook functionality with Apple’s innovative new phone. The successful candidate will complete both documented and adhoc testing to ensure high quality releases.

The hope is that an Exchange connector for the iPhone is in its final testing phase.

Watch for an announcement from Apple that a new version of the iPhone has built-in support for Exchange Server. If that’s coupled with an upgrade to permit the iPhone to use AT&T’s higher-speed data network instead of the godawful slow EDGE network, it will make the iPhone a much more attractive choice.

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