Clouds of Confusion

“The cloud” is touted as one of the biggest advances of the current era. And it promises to be: having information stored centrally and synchronized seamlessly across multiple devices would be a dogsend. The operative word being “would.” There are a few potentially faulty assumptions here, one of which is that there is a single “cloud.” And there is also a catch: that is, the “multiple devices” bit. Just how many, and of what capabilities, are we talking about?

It turns out that when you start to mix and match, as invariably happens in real life, things become slightly more complicated. I have encountered this recently when trying to understand exactly how and where all the data is flying around between and among my two Macs and my iPod touch, and MobileMe (personal information) and Exchange Server (work). I had quite a time putting together the following diagram, but I think it is accurate.


The iTunes sync from the Mac Pro to iPod touch is tethered; everything else is wireless on wired internet. I should note that this is actually a simplification of my setup: I have several private domains as well. But it gives a good picture of the problem: by default, not everything is synchronized, or synchronized live. And I’m using a single vendor (Apple), at least for my devices. First, due to what appears to be a bug, address book information doesn’t work between Exchange Server and Macs—though on the iPod touch this is not an issue. However, for me the crux of the problem is trying to undertand why only mail is “ON” (whatever that means) by default:


There’s nothing to indicate what “ON” versus “OFF” means. My address book and calendar are synced via iTunes; as an expert user, I made the leap to assuming that this means “over the air” sync, rather than depending on a tethered sync via iTunes. But when I flip the switch to turn on, say, Calendars, I am presented with what I think may be the most confusing dialog message I have received in thirty years of computing:


I defy anyone to explain to me, based solely on the message and buttons, what this means. I spent half an hour today chatting with an Apple support representative, and I’m not convinced that he fully understood either.

  • Of course there are calendars on my iPod not synchronized with Exchange; of all vendors, one might think that Apple would make the assumption that living in an all-Microsoft world isn’t necessarily the norm.
  • Would I like to merge the (non-Exchange-synced) calendars with MobileMe? Well, they’re already synced with MobileMe via iTunes. What is the difference between “syncing” and “merging”? Will the latter duplicate information?
  • Which “server-based calendars” are being referred to here: MobileMe, Exchange, or both? I assume “removed” is a synonym for “deleted,” but removed from where? My iPod, Exchange, and/or MobileMe? Scary.
  • What is the difference between “Do not Merge” and “Cancel”?

I’m going to take a chance—while I’m writing this post—and tap “Merge with MobileMe.” I have backups.

After proceeding, I get a progress message, “Turning On Calendars…”. This lasts for a long while (at least five minutes), until finally I stop tapping and the iPod turns off its screen. When I rouse it again, the Calendars setting is “ON”.

And what is the result? I created a new event on my iPod touch, and it has appeared on MobileMe without a tethered sync. So much confusion and stress for something that should have been set up by default. If it took me this much analysis and thought, what is the lot of the average user? Synchronization strikes me as a complex development challenge, but it should be the default: that is the promise. If Apple hasn’t got it right, what chance do we have?

Now I’m going to try turning on Google sync …

5 thoughts on “Clouds of Confusion

  1. “There are existing calendars on your iPod touch not synced with Exchange. Would you like to merge them with your MobileMe account? (Server-based calendars synch with your Mac will be removed.)”

    I read the dialog message and I presumed immediately that “Server-based” would imply MobileMe instead of Exchange as you are in the MobileMe application. It seems that the act of merging is an action MobileMe can simply do between your Mac devices and not Exchange. Of course, eventually you found out that it did exactly that.

    I see your point that an average user would be confused. “Servers?!! Server-based?”. The message seems to be a catch-all phrase. Perhaps it should indicate exactly to the user that new calendar events in your IPod (from Device 1) will be added into MobileMe (to Device 2). Since I work with merges a lot, I easily understood what it meant.

    • Of course, you understand it at least in part because you’re a developer! I hear what you’re saying, although this is not in a MobileMe application, it’s in the Settings app.

      I’m not sure why the message even bothers mentioning Exchange, as none of the choices affect your account there—and there is no un-merged way of syncing with Exchange. I am uncertain what would happen if you tapped the “Do not Merge” button: would you then have two copies of each of your calendars and address book entries which were previously synced via tethering to iTunes, e.g. “Personal” and “Personal (not merged)”?

      My main point is that over-the-air should have been set up by default. The only reason I can think why they would have made tethered sync the default is because it was, with “classic” pre-iPhone and iPod touch iPods, the only way of syncing, and there may have been an assumption that users would be confused if a sync didn’t happen when docking their new device. But that would be a weak assumption, in my opinion, as it would be obvious that syncing was happening automatically. Of course, if you didn’t have a MobileMe account or somewhere else to sync to, tethered sync could be the default.

  2. I got a similar virtually useless dialog when trying to enable Contact syncing on the iPhone: “There are existing contacts on your iPhone not synced with Exchange. Would you like to merge them with your MobileMe account?”

    I’ve read it a dozen times and have no idea what it means. I had pretty much the same thought process you had:

    – First of all, why does Apple feel the need to present me with this warning? Do I need to worry about a cliff I’m about to fall from? By proceeding, I have to assume the safety of my contact list is now in danger.

    – Why the heck do I care that some of my contacts aren’t synced with Exchange? Again, what does this warning even mean?

    – Which of the choices presented is going to pollute my work account (Exchange) with my personal information? It sounds like I have a choice: (1) risk screwing something up; or (2) don’t sync. I’m so glad I spent $$$ on MobileMe for this ambiguity.

    – What does merging “them” with my MobileMe account even mean? Would this change my addressbook immutably in some way?

    Here’s an even better question: If I choose “Do not merge”, will this dialog disappear forever? What if, after finding out the effects of “Do not merge”, I decide I want to try “Merge with MobileMe”. Will I even be given the option again?

    I’m sorry, but this is ridiculous. Searching on Google doesn’t really find a thorough explanation of what the heck is going on. After your experience on the phone with Apple, I’m not even going to bother spending time on that phone call.

    So I’m paralyzed at this point. I don’t want to screw anything up with my contacts (especially my Exchange-based contacts), so I guess I can’t sync them. I hope Apple figures this out. Not to disparage developers (of which I am one) but this sounds like a dialog that slid beneath the radar of the usability group. Unfortunately, the dialog is virtually meaningless to the end user. It’s more mechanical, something along the lines of, “There is an exception which has occurred.” Just tell me the house is on fire so I can get out.

  3. Hi David, I tapped “Merge with MobileMe” and everything Just Worked after that, even after I migrated to an iPhone 4; my work and personal information are kept separate. I’ve not seen the dialog since. I don’t know what “Do not Merge” would do, but it’s probably not the behaviour you want.

    (I get a relatively high number of hits on this page, indicating to me that people are frequently scouting around for and answer to this dilemma.)

  4. Chris –
    Thanks for your bravery to try out the “Merge…” for us! I was paralyzed with fear until I found your site on Google search! Hitting “Merge” right now….

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