The iPhone and Exchange, Part 2

Two weeks ago, I wrote a column about the release of Apple's iPhone and what it might mean for Microsoft Exchange Server admins ("The iPhone and Exchange," July 5, 2007). The column was somewhat in the same vein as a vegetarian teaching people how to grill steak, because I hadn't used an iPhone yet. I got one the day after submitting that column and have been using it heavily since then. Now I'm ready to spill the beans on how it really works with Exchange.

Let's get the easy part out of the way: Everything you've heard about the fit, finish, screen, and UI quality is absolutely true. The iPhone is a beautiful device with a gorgeous interface and a screen that's better than I've seen on any other device. But so what? Beauty is only skin deep, after all, while ugly goes clear to the bone. In this case, "ugly" isn't quite the right word to describe the experience of using an iPhone with Exchange, so "deeply flawed" will have to do.

When you create an "Exchange" account on the iPhone, it uses IMAP, but the configuration makes for extra steps in the UI. For example, the iPhone interface hides the Calendar, Contacts, Tasks, and Journal folders, and it will hide meeting invitations and other types of Exchange-generated messages.

Probably the least flawed part of the device is—surprise—the onscreen keyboard. I've always avoided phones and PDAs that don't have a physical keyboard, so I was prepared to dislike the iPhone keyboard from the start. However, Apple's much-ballyhooed software for correcting typing mistakes works quite well. I still miss the tactile feedback of Palm's excellent Treo keyboards, but I found the iPhone keyboard usable.

A bigger flaw: The navigation interface for moving between accounts and folders is awful. From the iPhone home screen, you tap once to get to the account selection page, then again to pick an account, then again to choose the Inbox folder. If you want to switch to the Inbox of another account, that requires another four taps. Navigating within the folder tree is a hassle because the tree is always expanded—there's no way to collapse folders, meaning that if you want to get to a folder named "Work orders," you have to scroll through several dozen folders of RSS feeds under "Blogs." Not that I'm bitter about it or anything.

Moving on to the most serious flaw: When you delete messages, they aren't deleted. Seriously. By default, the iPhone never purges IMAP messages from the device! That's so 1985. You can turn on purging, but the minimum delete interval is 24 hours, during which time those messages are still visible in Microsoft Outlook, Microsoft Entourage, Pocket Outlook, or whatever other distributed authoring and versioning (DAV), MAPI, or Exchange ActiveSync client you use. That's simply unacceptable. If you're using a "regular" IMAP client, you can tell it to expunge the messages, which forces them to disappear. However, this isn't a useful workaround unless you're already using IMAP.

Another flaw that's only slightly less bad than the expunging problem is that there are very few options for choosing which messages you want on the device. In fact, there are few options at all, for anything. This is typical of Apple, which has long been known for restricting the number of knobs and buttons that users can fiddle with. This approach often produces an appealing simplicity; equally often, it gets ordinary users frustrated and angry.

The iPhone has a few advantages as an email client. Its rendering of HTML messages is excellent, and the large screen makes it easy to read complex messages. It's got lots of storage space, so you can usually store many more messages than you can fit on a typical Windows Mobile device (which is a good thing, given its lack of synchronization controls). Its ability to use Wi-Fi is a great bonus (yes, I know there are Windows Mobile devices with Wi-Fi; I've just never had one before), especially given the dog-slow speed of AT&T's EDGE network.

Overall, I'd sum up my iPhone experience by saying that it's a lot of fun to use as a media player and mobile Web terminal, and it's tolerable (barely) for use as an email client. Contrast this with my Treo, which rocks as an email device and is tolerable (mostly) as a Web browser. The solution, for now at least, is for me to tote two devices. The combination gives me the best blend of functionality and power, and I don't even mind when people ask me if I have more junk on my belt than Batman.

For more in-depth thoughts on my iPhone experience, see my blog.