In which I have come to hate updating OS X

I get to wear a lot of hats at idfive; everyone here does.  One of my favorites is pseudo-IT-guy…  or at least it was until we decided to upgrade the office from Snow Leopard to Lion to take advantage of the automatic document versioning.  I enlisted the help of our trusty social media guru, Aaron, and we set about figuring out how we were going to update 8  machines with the new “App Store only” process Apple had laid out.

First step: call Apple.  Aaron spoke to an Apple representative who informed him that bulk licensing was only available in quantities well beyond our needs. He suggested making a number of company App Store accounts and purchasing the software through those for each machine. Individually.  The kicker?  You can’t attach the same credit card to each account or the universe will implode.  The Apple equivalent of dividing by zero or something.  “Gift cards,” the rep recommended.

Aaron ran off to the local Best Buy to pick up two $15 gift cards for each employee’s machine (the upgrade was $29.99) and returned with news that they only had the $25 cards in stock.  Since the entire balance of a card is applied to an App Store account upon redemption these were useless. He had gotten two so we could update our server, but everyone else was out of luck.  We had to order all the cards from the Apple store and wait for them to be delivered.

When the cards arrived, we added them to the accounts we had created for each computer, being careful to document which accounts were being tied to which machine and then went around and got everyone started on the upgrade.  Finally.  We spent more than double the time we had estimated to our boss; time we couldn’t spend helping clients/making money for the business.

The whole experience was terrible.  I understand that Apple can’t support bulk licensing at such a small scale, but they need a better way for businesses to upgrade. I suppose we could have waited for the physical release and paid more than double for each license, but that makes about as much sense as gift carding…

And then this morning Bill sent me a link to this article about the next OS X which is almost in developer release.  I broke out in cold sweats and curled up in a ball under my desk which is where I’ve been typing this from.  I really hope Apple improves the upgrade experience for small businesses or I don’t know how we’ll be keeping up with the yearly releases.

Could someone pass me the tin foil?

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