OS X Update to fix Apple Configurator wasn't the best choice.

So I’m partially posting this to vent and partially to inform those who may be considering an OS X update to fix their Apple Configurator woes and aren’t 100% sure:

I manage a small(ish), new(ish) iPad circulation program at our Library (we loan a set of iPads out to university students) and I also tend a set of in-house iPads used by library staff. I’m running a 2011 Mac Mini (Server version) and had OS X Lion installed as well as the Lion Server app for pushing apps out remotely in specific situations (and for some other basic server functions).

This morning I found a July 10 2013 support document that I hadn’t noticed before which explains a problem I’ve been having since updating to Apple Configurator v 1.3 (the software that I’m using to manage the circulating iPads).

http://support.apple.com/kb/TS4613

The solution is to either downgrade to Configurator 1.2.1 (not an option, really) or to upgrade to OS X Mountain Lion. And it’s really not like I have a legitimate choice to do nothing. When the article says Configurator “may quit unexpectedly” it really means *always* quits when an iOS device is plugged in and requires a restart of the app – with it functioning for a short period of time before crashing again. So I got ahold of our purchasing people and in the end bought and installed the $20.00 update to OS X Mountain Lion despite the fact that Mavericks is on the horizon. Problem solved.

SORT OF.

In the process, the Lion Server app simply stopped working. After the OS update, trying to open the app just gives a small dialogue box that states that Lion Server doesn’t work with the new version of OS X. So I thought to go update to the latest version, just like with every other piece of Apple software. Except that this piece was going to cost an additional $19.99 to update.

Thinking that there must be some mistake, I contacted Apple and spent well over an hour between online chat and phone support – probably closer to two, becoming increasingly frustrated. Perhaps I don’t have the background in earlier versions of OS X Server which would have clued me in that each version of the server software is tied to a specific version of the OS? I referred to the following document prior to upgrading to OS X Mountain Lion and was reasonably sure that the Lion Server software would continue to function after the update – I never expected any additional functionality from it, of course. Besides, the OS update was simply to make Configurator work again!

http://support.apple.com/kb/PH8043

This knowledge base article specifies (at least as of the morning of 7/22/2013) that the OS requirement to install Lion server is Max OS X v10.6.6 or later; v10.6.8 recommended. To me, this meant that since v10.8.4 is later than that, it would continue to function. In any case Apple had zero sympathy for this situation. I was told by someone to whom my case was escalated (some sort of 'enterprise supervisor' guy) that I could spend $19.99 more to upgrade to the next version of OS X Server, or that I could take a loss on the $19.99 already spent and revert back to OS X Lion – all while acknowledging that Configurator would again cease to work if I reverted to Lion.

When presented with the documentation about Lion Server requirements he repeatedly assured me in an eerie example of doublethink that the article was both completely accurate, yet somehow NOT accurate because “Lion Server is for Lion”. He reiterated both its complete accuracy and its obvious inconsistency several times.

In the end, I’ve had to shelve all OS X server functions for now (as I no longer have functioning software) because I don’t want to spend more now on an upgrade…and then have another OS update AND Server update again in a few months. Yes, perhaps I was naïve in not equating the various ‘cat’ named OS versions with the cat named server app versions; not realizing that a piece of software with the name “lion” in it wouldn’t function once a version of Mac OS was installed that prefaced it with “mountain.” The fact of the matter is, the documentation I could find said that Lion Server needed OS X v10.6.6 or later to run, and this absolutely isn’t the case.

Sorry for the long post, but this whole thing has left a bad taste in my mouth – definitely not the taste of the Apple I’ve heard of and come to know over the years. I was even told by the first phone contact person that “they [meaning, I assume, those in charge of documenting /implementing/marketing new versions of Apple software] don’t go out of their way to tell you when an app is going to stop working.” And I’m sorry, but that smacks of a company like Microsoft at its worst, not Apple at is best.

Thanks for reading.