Deathmatch: E-mail, calendars, and contacts
I fully expected the BlackBerry to beat the pants off the iPhone when it came to e-mail. So I was shocked by how awkward e-mail is on the BlackBerry.
In both cases, I used a personal POP account and a work Exchange 2003 account. The iPhone works directly with Exchange, so my e-mail, e-mail folders, calendars, and contacts all flowed effortlessly among the iPhone, laptop, and server. The configuration was trivial. For the BlackBerry, I first used the BlackBerry Internet Service (BIS), which acts like a POP server: You can't access your Exchange folders, contacts, or calendars. And man, is the setup painful, as you step through seemingly countless Web-based configuration screens. After struggling with the limitations of BIS, I asked our IT staff to connect me to our BlackBerry Enterprise Server (BES) instead, which gave me the connections to folders, contacts, and calendars.
It's key to note that BES supports Novell GroupWise and Lotus Notes, while both of those servers support the iPhone only through Web clients, limiting their integration with other iPhone apps such as Contacts and Calendar. (IBM says it will soon add ActiveSync support to Notes, which will then let it have a native iPhone client at some point.) Thus, BlackBerry supports more e-mail systems, even though you have to add a dedicated server to get that support (and upgrade to the latest version to support app management). But an iPhone is much easier to use with Exchange than a BlackBerry is -- at least as a user. Apple uses Exchange Server 2007 for remote iPhone management: remote kill, configuration, and so on. Apple also provides a free app that lets IT admins manage profiles and internally developed iPhone apps on the devices. The hitch is that the management tool can reach the devices only when they are physically tethered to the admins' computers.
My first struggle with the BlackBerry involved its puzzling timestamping of e-mail messages. Oddly, the BlackBerry lists the messages according to when the device receives them, not when they are sent. (If you open the message, you can see the real date and time.) The first time I told the BlackBerry to "reconcile messages" with the server, so I'd have older messages (past my 30-day setting) available to me, in they flooded -- all stamped with the current date and time, burying my new messages. Each time I got off a plane or turned the BlackBerry on after charging it, all the messages received during those disconnected times would be marked as more recent than the messages I got right after I turned the BlackBerry back on. It makes e-mail management a nightmare.
The second frustration was discovering how hard it is to navigate e-mail. I use folders extensively to manage my messages, and the iPhone makes it very easy to navigate among folders. The BlackBerry lets you navigate down but not up, so it's hard to flip from any one folder to another. And on the BlackBerry, the original message stayed in the top-level inbox, so now the message existed in two places: my too-cluttered inbox and in the folder to which I moved the message from my computer. Fortunately, there is a preference to turn that dual message location off; too bad it's not the default.
Reading e-mail was comparable on both devices, though the iPhone's larger screen requires less scrolling. I prefer the iPhone's on-screen controls for replying, forwarding, and so forth over the BlackBerry's use of its button to open a contextual menu, but that's an acceptable UI-based difference. Still, the BlackBerry's menu is too long and requires too much scrolling for common functions. It's easier to delete messages on an iPhone, both in the list and when reading a message, than on the BlackBerry. The culprit is the BlackBerry's reliance on the step-intensive contextual menu for almost everything you do. And while you can press the Backspace button to delete mail, you still have to contend with the menu to confirm the deletion.
The BlackBerry and iPhone are mixed bags when it comes to navigating messages. Both the BlackBerry and iPhone offer a quick way to jump to the top of your message list, but only the BlackBerry has a way to jump to the bottom. The iPhone makes it very easy to select multiple messages to delete or move them, while the BlackBerry can only multiple-select contiguous messages, which in practice means you can't work on many messages at once. There is a workaround for some situations: You can search your messages by name, subject, title, or attachment status, then select those files -- still contiguously -- to work on them.