Upgrade Woes for iPhones... Again

Apple and business users. Are we there yet? Is Apple really ready for the enterprise? Nagging doubts won’t go away as long as Apple struggles with reliably delivering software, upgrades and enterprise features. The latest in the saga of upgrades and stranded users with bricked phones is the simultaneous iPhone 2.2 software and iTunes 8.0.2 upgrades that occurred this past weekend. I became aware of the problem through my good friend and security blogger Alan Shimel, who called me tonight about his experiences with his newly bricked iPhone that happened while on holiday with family.

Apple’s solution to the problem? You must have a second computer to get the upgraded 2.2  iPhone working again. Or drop by an Apple store and have them fix it. Just how you wanted to spend time on your family weekend, more or less a business trip, visiting the Apple store or spending your own time and brain cells on the phone with Apple, trying to get your iPhone back to square one by recovering your data and so you can use your phone again.

Alan sums up his frustrations at the end of his blog post, (not all of which I can repeat here):

Yes Apple stick with music players and letting elementary kids play computer games. But stay the heck out of the enterprise until you get your act together and build a company for grown ups!

Technology like smartphones aren’t optional items like a music player. So many things could hinge on making or receiving that phone call, sending or receiving an e-mail or attachment. Being out of pocket can cost real dollars, and business users are willing to pay for that extra convenience and reliability so they don’t find themselves disconnected from business activities. Same is true of applications and services in the cloud. Maybe my photo service can be down but do something that prevents the transacting of business and again we’re talking real dollars. And Apple's still struggling with the issues of its hosted services, much like we saw when iPhone 3G orders and iTunes upgrades overwhelmed Apple's servers. Kind of sounding familiar, isn't it.

I know, I’m flying in the face of all Apple’s success, both selling iPhones and their financial success. But the Achilles' heel of Apple has always been the business user, which of course is where companies like Microsoft and RIM have been able to dominate. Business users will always be faced with swimming up stream by trying to get IT to support Apple devices. At least we don’t see anything yet to break that trend.

And experiences like Alan’s, repeated by hundreds or thousands of users, including those who rely on their iPhone for transacting business, show the challenges that still remain for Apple to truely move into the business marketplace.

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