What's wrong with Mac OS X Snow Leopard

A few business-oriented features fall short for enterprise usage

There's no doubt that Mac OS X 10.6, aka Snow Leopard, is a worthwhile upgrade -- a no-brainer for people with Intel Macs. I've pointed out the 7 best features in Snow Leopard, and my three-part series of slideshows details the many enhancements in Snow Leopard for all users, for office users, and for power users.

But Snow Leopard has a few flaws that should not go ignored in the enthusiasm for its many strengths. In fact, some of the more welcome additions to Snow Leopard also house some of the bigger disappointments. By not going far enough, Snow Leopard's support for Exchange 2007 and Cisco's VPN protocol are chief among them.

[ Get details on new Mac OS X features in InfoWorld's "What's new in Mac OS X Snow Leopard" slideshow trio: new features for all users, for office users, and for power users. | Discover the 7 best features of Mac OS X Snow Leopard. ]

It's no secret that Apple has had a conflicted relationship with the enterprise for years. But when Apple switched to the Intel CPU and Parallels created virtualization software to allow Macs to run Windows side by side with Mac OS X, individuals stopped having to worry about whether Apple formally supported the enterprise -- Macs could fit in very well on their own, leading to a significant rise in business usage of the Mac.

Fast-forward to a year ago, when Apple introduced enterprise capabilities such as Exchange support and Cisco VPN to its iPhone and said it would bring the same capabilities to Mac OS X. With Snow Leopard, it has, but as with the iPhone's enterprise support, Apple stops just shy of doing it right. So while Snow Leopard is an even easier fit as a corporate PC, it continues to have unnecessary limitations that will make IT -- especially in larger organizations -- resist the Mac.

Mail's Exchange capabilities aren't quite enterprise-class
Configuring Snow Leopard to work with Exchange 2007 is a snap; the auto-setup routine usually does the trick, and the setup screens for manual configuration are easy to work through. Apple's Mail, iCal, and Address Book clients are fast-loading, capable apps that let users avoid Microsoft's bloated, incredibly slow Entourage 2008, which has long been a problem for corporate IT, offering fewer capabilities than Outlook and more balkiness when working with Exchange Server.

In fact, even Microsoft has finally admitted that Entourage is junk, saying it will dump the program in favor of a Mac version of Outlook when Office 2010 ships. In the meantime, Microsoft's reworked version of Entourage, called the Web Services Edition, has an embarrassing bug list -- since removed from Microsoft's site -- that doesn't bode well for the future Mac Outlook.

So Snow Leopard's native Exchange 2007 support promises to allow both IT and users to get rid of the balky, buggy, not-quite-compatible Entourage in favor of Apple's snappy, better-designed collaboration apps. Except that Apple stopped short of implementing two capabilities in the now-Exchange-savvy Mail that will cause many organizations to stick with Entourage -- thus making the native Exchange support irrelevant.

One miss is that Mail has no ability to set up an away message in Exchange, as Entourage 2008 can. So Mac users must use Webmail to set up away notices -- a silly inconvenience.

[ Get all the details on the new Mac OS X in the "Mac OS X Snow Leopard Bible," by InfoWorld's Galen Gruman and Macworld U.K.'s Mark Hattersley. ]

The other miss is that Mail doesn't support Exchange's delegation feature, so users can't access others' mailboxes. That feature is commonly used by admin and support staff, for example, to monitor their boss's e-mail or a general help mailbox. There's no work-around to this issue. What's particularly galling is that iCal does have delegation capability -- so admins can manage their boss's calendar, for example. Why Apple didn't implement delegation in Mail as well is a mystery.

Cisco VPN feature not suited for enterprisewide management
There's a similar "stopped too short" issue with Snow Leopard's support for Cisco VPNs: You can't import PCF files, so IT must manually enter the shared credentials on each Mac -- and manually update each Mac when those change. You can't send employees an e-mail with the revised PCF file and let users import it, as you can with the Cisco VPN client software. So most businesses will end up sticking with the separate Cisco VPN client instead of taking advantage of the one built into Snow Leopard. (Those that do are advised to use the most current version of the Cisco VPN client; in my testing, the 4.9.01.0180 version worked, but some earlier 4.9 versions did not.)

For a company that practically invented seamless user experience and plug-and-play, these "stopped too short" issues are unfathomable and unnecessary. Here's hoping for a quick OS update. My fear, though, is that Apple will ignore the issue; after all, the iPhone OS still can't support .ics calendar invitation files or Cisco VPN PCF files a year after the iPhone OS adopted the same business technologies now part of Snow Leopard.

Flight detection not so savvy
Fortunately, there are not a lot of other flaws in Snow Leopard's capabilities.

One fix I hope Apple makes is to its new Data Detector for airline flights. Data Detectors are agents that scan text in Mail, TextEdit, and other (usually Apple) applications for certain kinds of content, such as dates or phone numbers, and offer pop-up menus for that data to let you work with it. For example, if you hover your mouse over a date in Mail, the pop-up menu that appears lets you create a calendar appointment.

Snow Leopard adds a Data Detector for flights to offer a "see the flight status" capability, but it only recognizes flights that use an airline's two-letter codes, such as "DL 589." Many reservation confirmation e-mails spell out the airline's name to be user-friendly, but Snow Leopard can't see those. So if your confirmation e-mail says "Delta Air Lines 589," Snow Leopard won't know it's a flight and not give you the oh-so-convenient option of checking the flight status with a single click.

One wish for a change
There is one changes I wish Apple had made in Snow Leopard: Although widgets never took off as expected given the hype a few years ago, Apple should still make its widgets work better. When you launch a widget (an applet), you lose access to the Finder, desktop, and all running applications -- and that's silly. Widgets should run like apps, allowing you to switch among whatever you want. Windows Vista and 7 do this right; so should Mac OS X.

All in all, there's not much to complain about. Still, Apple should have taken its business outreach all the way. Here's hoping it does so soon.

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