You can, of course, access calendar and contact data without connecting through the desktop by tapping Exchange or Notes Web access via the iPhone's Safari browser. Unfortunately, navigating those desktop-oriented pages even in the iPhone's fairly large screen makes this method a somewhat frustrating quick fix.

Another access issue to consider is that the Safari browser in the iPhone does not support Java or ActiveX, so Web pages that use these applet-delivery technologies won't run on the iPhone. ActiveX is a Microsoft technology available only on Windows, so the iPhone's lack of support mirrors the Mac's lack of support, but the lack of the cross-platform Java technology on the iPhone is less justifiable for Apple. (Note that it does support JavaScript.) But Sun is coming to the rescue there, promising to develop a Java virtual machine (JVM) for iPhone this spring, with a release planned for summer.

Securing the iPhone
The biggest issue for IT when it comes to the iPhone has been security, even with the availability of SSL authentication for securing e-mail connections. Make sure your Exchange or Domino server requires SSL and one of these SSL options: MD5 challenge-response, NTLM, or HTTP MD5 digest. The iPhone also supports password-based SSL authentication, but that can be more easily spoofed than the other options.

All SSL does, however, is encrypt e-mail messages, not any other traffic between the iPhone and the company's servers. Typically, you would mitigate this concern by using a VPN client -- or a BlackBerry or Motorola GoodLink server and its proprietary secured network -- as the conduit to safeguard all traffic with the iPhone.

The iPhone didn't originally support VPNs, but Apple added that capability via a software upgrade in late 2007. The iPhone's VPN capabilities are solid -- comparable to Windows Mobile and Palm OS devices -- with a choice of L2TP and PPTP protocols and support for EMC RSA Security's SecurID key-based authentication. (You access those through the General preference pane's Network option.) But the iPhone VPN client does not work with all VPNs; Cisco-based VPNs in particular are incompatible unless they are set specifically for Mac OS X and iPhone compatibility. The June iPhone software update will improve VPN capabilities by supporting Cisco IPsec and two-factor authentication, certificates, and identities, Apple said,

Three security issues have caused the most complaints from IT, when compared with Windows Mobile, Palm OS, and BlackBerry. Apple plans to address all three in the June software update, though the details are not yet fully clear.

First, the iPhone has not provided device encryption, meaning that any data stored on the iPhone can easily be obtained by a thief. With nearly 16GB visible to PCs as an external drive when connected over USB, the iPhone can store a lot of could-be precious corporate data.

Second, password protection on the iPhone is scant. More than providing a four-digit maximum for passwords, the iPhone has provided no way to enforce password use or policies as users can simply turn the password feature off.

Third, the iPhone's lack of a remote lock or kill feature has left IT in the lurch if the device is stolen or lost.

Apple said it will add on-device encryption, IT-manageable security policies and remote-kill features as part of the iPhone 2.0 update, though it is unclear whether this means IT will need an iPhone-specific management tool or can use popular management systems they likely have already deployed. Apple is making the new software available before the June release to IT organizations willing to test the beta version.

In the meantime, IT will have to decide whether these three security shortfalls justify banning the iPhone from the enterprise until the new software is out and its capabilities better understood. A good way to judge that is to make an honest assessment: Are you as tough on USB thumb drives, smartphones, and work-at-home users' PCs as you want to be on the iPhone?

Related articles
Outfitting the iPhone for business
Executive pressure is pushing the iPhone through the side door of the enterprise, but will the CEO's crush object ever truly be business legit?
Review: iPhone: The $1,975 iPod
Apple's and AT&T's high-price gadget is a heartbreaking triumph of greed over genius
Review: Supersmart phones for extreme mobility
We pick seven serious business phones with all the bells and whistles, plus the power and flexibility that real mobile professionals need
Video: Two Geeks and an iPhone: Part 1
What we use and why
Video: Two Geeks and an iPhone: Part 2
Tips and tricks for e-mail, safari, and more
Video: Two Geeks and an iPhone: Part 3
How to add third-party apps to your iPhone
Thoughts on the iPhone/iPod Touch SDK
Enterprise comes to iPhone
15 things Apple should fix in iPhone 2.0

Note: An earlier version of this story published on March 3, 2008, did not include any information on the iPhone 2.0 software update's capabilities