Fortune has a short analysis piece up looking at Apple's need and odds of penetrating the enterprise market with the iPhone.

They see the same basic problem with the premise that I do: Apple's support system is simply not designed for and is inadequate to handle corporate IT requirements. I extend that problem to Apple's attempts to penetrate the corporate market with any of their products, as I have previously noted.

Fortune mentions that it appears that Apple is making efforts to woo enterprise customers now, but my impression is that they are lukewarm, individual efforts, not components of any sort of strong, considered, mandated corporate strategy in that direction. And anything less than a major effort will fail, at least on the traditional field of corporate sales.

The avenue left appears to be the one that Apple is taking, which is to rely on guerilla adoption of the devices at all levels, and then to allow internal pressures to force corporate IT to integrate the devices. This is sure to raise hackles among CIOs who pride themselves on maintaining security, interoperability, and budgets, and probably won't do Apple any favors in the long term... they may sell a few more iPhones, but they won't be disposing anyone to buy their desktop or server products. CIOs don't like having technology forced down their throats, particularly not by end users more concerned with being trendy than standardized.

Apple's best bet may be to use the opportunity to encourage a different sort of Information Technology paradigm, one which I have termed "Fragile Support" that off-loads the responsibility for procuring and securing such personalized devices onto the user and their selected provider by using virtualized and black-boxed services which render the device at the end of the chain more or less irrelevant from the IT perspective. This, as I see it, is one of the ultimate benefits to the Service Oriented Architecture, although it is as of yet off the radar of most major proponents of SOA, who are still looking at the benefits internal to IT. This trend is coming anyway; for Apple to seize on and push it as a platform for iPhone sales could also smooth their entry into enterprise IT in general.

The approach is sure to garner considerable suspicion; Apple is not traditionally considered a voice of reason and wisdom in the corporate IT world. But as SOA projects begin to bear fruit, and cutbacks are mandated, the combination of capability and internal pressures may nudge enterprise CIOs in a direction which will dovetail favorably with the opportunity to release certain measures of control and make users happy by allowing them to procure and operate technology which they favor rather than that which has been selected by some faceless IT procurement committee.