Usability problems with .Mac sync

I’m afraid this is another of those entries outlining bizarre design decisions and perplexing usability quirks in the otherwise brilliant world of Apple computers and phones. The problem is sync. It can be done, but it often goes wrong, even for smart people who understand computers, haven’t hacked their equipment or broken the law, and are kind to dogs, cats, and children.

Here’s a particular setup: .Mac account. Tiger laptop at home, Leopard iMac at office.

On both Macs, you need to refresh your subscriptions (Calendar: Refresh All) before you sync for the first time at that location. Otherwise, sync deletes the subscribed calendars’ information. Just wipes it clean away.

And even if you Refresh All first, sync may wipe away your data, just because.

Fortunately, after sync erases your data, hitting Calendar: Refresh All again reinstates it, downloading saved data from .Mac.

Why does syncing on either Mac remove all the calendar events from subscribed calendars? It’s the opposite of what any user could possibly want. There’s not even a conceivable edge case where a user would expect “sync” to mean “I’m bored with my life. Surprise me. Make my calendar data disappear.”

One doesn’t sync to lose data. Losing data by syncing is the exact opposite of what a user expects—which also makes it the opposite of what the Macintosh experience promises and usually delivers.

.Mac sync is either partly broken; or correctly designed, but to absurdly limited scenarios; or designed so counter to a user’s expectations that it should only be run with instructions, which Apple does not provide.

Apple does not provide instructions because instructions imply a learning curve, and Apple’s pitch is that its stuff just works. One nevertheless expects at least a slight learning curve when using, say, GarageBand or Keynote. But not with sync. “Sync now” seems pretty self-explanatory, and no user doubts what’s supposed to happen.

Sync does give you a warning before dumping your data, and that warning provides a clue to what’s going wrong. It tells you that syncing will remove x number of items from your calendars, and even lists which items they are. In Leopard, it goes further, and shows you before/after views of items that will change.

Significantly, there is generally no change at all between the before and after views. Probably the “change” is to a part of the database that the user doesn’t see, and has to do with differing file formats or differing time-stamp conventions between Tiger and Leopard. A less buggy or better conceived interface would hide this non-information from the user instead of asking her to think about it.

Do I really need to see that “Lunch with Jim at 1:00″ is going to “change” to “Lunch with Jim at 1:00?” Probably not, since, from my perspective as a human, the two items are identical. It’s lunch. With Jim. At 1:00.

If “Lunch with Jim at 1:00″ is “different” from “Lunch with Jim at 1:00″ to my Macintosh because Leopard and Tiger encode or store calendar items differently, or because Leopard and Tiger time-stamp event creation dates differently, that’s not information I need to know and it’s not a before/after view I need to see.

Before/after seems cool, and probably is if your data is actually changing. For instance, if you’ve changed one of your friend’s photos, it would be nice to compare the before and after views and decide which photo you prefer. But I’ve never seen before/after work that way. Changed photos just get changed. Before/after only seems to come into play on my networks when “Lunch with Jim at 1:00″ is changing to “Lunch with Jim at 1:00.”

The irrelevancies I’ve just described must be endured, and the sequence (Refresh: All, then Sync, then Refresh: All again if data was lost during sync) must be performed in the order described, before syncing the iPhone. If, in a moment of derangement, you plop your iPhone onto its dock before doing the herky-jerky data dance I’ve just described, you will lose data not only from your iPhone, but also from .Mac, and then you will never get your data back.

Your mileage may vary.

There are always 100 people for whom everything works correctly, and some of them are always moved to tell me it works for them, and to imply that I’m somehow to blame for the obvious usability problems I’m clearly describing.

They are followed by a dozen Apple haters who want to believe that the lengthy and detailed description of a specific usability problem proves Apple makes bad products, and anyone who claims to enjoy using Apple’s hardware and software is a “fanboy.” Juvenile homophobic and misogynist name-calling often accompanies these messages of hope.

Here’s what I am actually saying.

On my two-Mac setup where one is on Tiger and the other on Leopard, I can make sync work, but I must carry out actions in exact sequences, and know the tricks to undo the damage that syncing inflicts on my data due to bizarre design decisions on Apple’s part.

A few times I have irretrievably lost data, although I was able to manually recreate it by emailing colleagues and asking, “When are we meeting?”

It reminds me of running an old analog mixing board in a dirty, smoky recording studio. Everything’s cool if you know which faders you must never touch, which inputs are dead, and how far to the left you can pan a sound source before shorting out the system.

There’s genius in the concept of sync, and it works magnificently when you’re, for instance, syncing just one iPod to just one Macintosh, always the same iPod and Macintosh.

It gets weird when syncing from home to office via .Mac across operating systems, and weirder when you throw hot iPhone action in.

How should sync work? Just like you think it should work. Just like the two arrows circling in on each other (sync’s icon) imply that it does work. Hitting sync at any time on any networked device should cause all the latest changes to be stored on .Mac and downloaded back to whichever connected device you’re using.

There’s a whole other discussion to be had on why the iPhone is supposed to sync to only one machine, (Sure, iPods do that because of DRM restrictions; but competitive PDAs can sync to any computer: home, office, you name it. Likewise with digital cameras. The iPhone is a phone, an iPod, a digital camera, and a PDA, but its syncs like an iPod, not like a digital camera or PDA, and that’s just dumb.) but we’ll save that one for a rainy day.

Sync long and prosper.

Addendum: Another crazy thing is that subscribed iCals from Basecamp don’t update upon refresh in Leopard. In iCal in Tiger, subscribed Basecamp iCals correctly refresh automatically when one selects Calendars: Refresh All. But in iCal in Leopard, subscribed Basecamp iCals do not refresh, period, no matter what one does. In order to “sync” Basecamp iCals in Leopard, one must delete the calendars every day, and subscribe to fresh copies. When one does this, one gets fresh calendar data, but sync fails due to “conflicts” that do not load in the frozen Conflict Resolver and thus cannot be resolved. This of course is not what Apple intended. It is, by any reasonable measure, an idiotic and self-defeating system. The basest ape would not design such a system. Obviously the system is not operating the way Apple intended. How does one fix it? Apple isn’t telling.

Comments are now off, but you can read what others had to say when comments were open.

[tags]dotmac, .mac, sync, iphone, imac, laptop, macbook, macbookpro, apple[/tags]

26 thoughts on “Usability problems with .Mac sync

  1. Jeffrey,

    i have a similar setup like yours. Synching one device (phone) with multiple macs is always asking for troubles. I have never done this, even in the days prior iPhone.

    The way i deal with it, is to simply pick ONE machine to sync my phones with. Logically, you pick the machine which you are at most of the time. In my case, this is my PowerBook. Then always only sync with this particular mac.

    Now if iphone would sync diretly with .Mac (which is the central synching hub and if you think about it, your macs also only sync with this one hub) via WLAN, we could circumvent all this and the problems would just go away, but as it is, synching will only work reliably between a Phone and ONE mac.

    The setup outlined above works well for me. I only sync on the PowerBook after i return home in the evening. I never need to sync at work where i have the computer in front of me all the time anyway and don’t need updated content on the phone as i can and do look it up on the mac.

    I don’t know why you would need to sync with two macs at all? Is it that your data changes so frequently, that you constantly need to synch your phone to your calendar and such because you leave your laptop at home while you change data at work and then are afraid to have stale content on the phone when leaving the office for lunch or such?

  2. I’m only syncing my iPhone to one Mac (my office Mac). It works fine as long as I first sync my office Mac to .Mac. If I don’t do that, then the old data on my iPhone will overwrite the data on my office Mac and on .Mac (it syncs to .Mac and my office Mac’s calendar at the same time).

  3. I’m with you on this one. I gave up trying to use .mac to sync between my Tiger desktop and Leopard laptop. Not only would I have to jump through hoops and put up with multiple warnings that, like you said, appeared to say I was changing something into the exact same thing, but I would also get duplicate calendar entries, seemingly at random, and other weirdness.I now use MissingSync (for my Treo 755p) exclusively to keep both machines in sync. My phone/PDA is now the conduit to sync the two.

    MissingSync isn’t without its problems, though. For some reason I keep getting multiple instances of phone numbers and email addresses in each Address Book record. Say, for example, the entry for Jeffrey Zeldman had a mobile number, office number, and email address. After a few syncs, that same entry will have 3-4 mobile numbers (all the same number), 3-4 office numbers, and 3-4 email addresses. Not sure why. (Also, I’m not 100% sure this wasn’t caused by trying to test .mac sync and still use MissingSync at the same time…I’m going to clean my Address Book now that .mac is turned off and see if the problem persists.)

  4. I had problems with Sync without even needing a .Mac account; apparently syncing a brand new iMac with a full iPhone address book means “erase all the contact data on the phone and replace it with the Apple Support number from the otherwise empty iMac Address Book.”

  5. I have troubles with iCal sync too, though not the same ones you describe. In my case, both the laptop and the desktop are Tiger. The trouble is that if I delete a calendar from my laptop, and run sync (expecting that it will be deleted from my desktop), sync wants to put it back on my laptop. So I actually can’t delete data from iCal unless I do it on both machines simultaneously and before sync runs. Annoying!

  6. Perhaps you might want to take a look at Spanning Sync ( It’s primary purpose is to keep iCal synchronized with Google Calendar but if you have it installed on two (or more) Macs then it will keep calendars synchronized on all the Macs. You can access an up-to-date calendar from any of your Macs, or through Google Calendar if you are away from your Mac. It’s $25 per year or $65 for a permanent license. No limit to the number of Macs you can install it on (it uses your Google Calendar sign-on to limit to a single user).

  7. You have saved me countless hours of hassle. I’m convinced to avoid sync for the time being. I owe you big time. What do you say I buy you lunch at 1:00? (signed) George.

  8. Jeffrey, sounds like hell to me. I know you posted about some of this before, and I mentioned trying to clean out your sync preferences, and I’m sure you tried that at some point, but I do have another guess, although this is purely a guess based on a weirdness when I got a macbook pro- is your iMac intel/Leopard? And your laptop is PPC/Tiger?

    I’m just asking because that seems to be where my problems arose, although my two PPC machines, the PowerMac G5/Leopard at home and the PowerMac G5/Tiger at work show none of these problems.

    Perhaps it’s something lodged in that set up somehow. Some conflict of endien organization or some such.

  9. I had problems with Sync without even needing a .Mac account; apparently syncing a brand new iMac with a full iPhone address book means “erase all the contact data on the phone and replace it with the Apple Support number from the otherwise empty iMac Address Book.”

    ZOMG. That happened to me, too! I forgot. When I first sync’d my iPhone to the new iMac (after all the data was migrated and checked for correctness), the sync wiped out all my data and replaced it with Apple’s support number.

    I forget how I got my data back; I think it involved some .Mac syncing and resets. Syncing the iPhone can wipe out CALENDAR information stored at .Mac but it doesn’t seem to wipe out CONTACT information stored at .Mac. (Because there’s no consistency, because, it seems, nobody at Apple did any kind of scenario-based user experience design.)

    Perhaps you might want to take a look at Spanning Sync ( It’s primary purpose is to keep iCal synchronized with Google Calendar but if you have it installed on two (or more) Macs then it will keep calendars synchronized on all the Macs.

    Thanks for the suggestion (others have suggested it too), but Spanning Sync is incompatible with Leopard for the time being (or it reveals a serious bug in Leopard, or both).

    Plus, my limited experience with Google’s calendaring stuff has not been sweet. Like, a friend exported her Google calendar as an iCal for my benefit. The iCal wouldn’t download. The problem seemed to be firewall-related. So I got a Google calendar account. That should solve it, right? But the iCal still wouldn’t download. The error message said feeds were broken. I guess I’ll have to fix Google’s feeds for them; maybe then I can download an iCal from their service, of which I am a member, and which I joined for the sole purpose of downloading this one fershlugginer iCal.

    What I think, with both Google and Apple, is that innovation is overriding usability. Some of the smartest minds in the world are innovating great new ideas, but in their rush to get them out there, they aren’t doing the patient follow-through that makes a product usable.

    It could be worse; there’s plenty of ugly, behind-the-curve software out there that’s also unusable. Bleeding edge and semi-usable is better than that.

    is your iMac intel/Leopard? And your laptop is PPC/Tiger?

    They are both Intel.

    The connection is fast, there’s plenty of RAM on both machines, there’s plenty of free hard drive space on both machines, there are no known disk or system problems. It’s just sync. Let’s call it a work in progress.

  10. Weird, i don’t have thiese problems anymore and my setup is similar. One desktop Mac runing Tiger, a Laptop running Leopard and an iPhone (both of the Macs are PPC though).

    I had sync problems when Leopard came out. Then i reset the sync data to one of my macs (don’t remember which one — i might even have reset it to the data from .mac) and since it runs pretty fine.

  11. What has fascinated me about this ongoing experience is how it clashes with my expectations as a pretty much non-Mac user. (I have an old one for testing websites.) Not even much of an Apple fan (my iRiver sees much more use than the iPod I won in a contest.)

    And yet, I’m surprised that it’s an Apple product is causing you grief. I’d expect this experience from the Windows machines I use all the time; Microsoft has conditioned us to expect bugginess.

    Until now, I hadn’t realized how completely Apple has conditioned me to expect simplicity and ‘just plain works’-ness.

    Darn. Now I have to go buy a MacBook.

  12. Same situations. I hounded IT at work to upgrade my work computer to Leopard so I could stop seeing “Deleting 526 Calendars” and “Adding 526 Calendars” in the same sync every day (with the conflict resolver telling me I had a couple hundred identical conflicts to resolve).

    Getting both systems on Leopard made things better

    Coincidentally, I was reading on Roughly Drafted last night an article about the complexities of sync challenges: Inside the iPhone: Wireless and Sync vs. Palm, WinCE

  13. I’m running Spanning Sync on Leopard and haven’t had any problems, though I do not have the iCal Birthdays calendar enabled (this seems to cause problems for some folks in Leopard). There’s a beta out of Spanning Sync which I believe fixes some problems and improves performance, but I haven’t tried it since everything works for me.

    With Spanning Sync you don’t need to export or download Google calendars — you just install Spanning Sync, match your iCal calendar names to Google calendar names and off you go! Also, with Spanning Sync I don’t see why your friend could not have just shared her calendar by adding you and you could have linked to the shared calendar with Spanning Sync.

    I’ve been quite impressed with how well and how easily Spanning Sync works. It might be worth a try since there’s a free 15 day trial. Or maybe think about it after the new version comes out of beta.

  14. I’ve been quite impressed with how well and how easily Spanning Sync works. It might be worth a try since there’s a free 15 day trial.

    That definitely sounds worthwhile, and I thank you for the tip. But if users need to buy a third-party product in order to get an Apple iPhone to sync with Apple’s .Mac and Apple computers, maybe it’s time for Apple to fine-tune some aspects of sync, so users of multiple Apple products have the good experience they associate with the Apple logo, instead of one frustrating experience after another.

  15. There are always 100 people for whom everything works correctly, and some of them are always moved to tell me it works for them, and to imply that I’m somehow to blame for the obvious usability problems I’m clearly describing.

    Thank you for saying this.

  16. My data loss issue was selecting to sync email accounts. Similar to the address book issue and calendar events, .Mac deleted all the accounts on my iMac that weren’t on the laptop. The absolute last thing anyone would want. Both machines are running Leopard.

  17. I find .Mac syncing works for most things I use it for: contacts and keychain seem reasonably stable, although I do back up by address book occasionally because it has been wiped clean in the past.

    However syncing calendars is – and has always been – something of a disaster. For subscribed calendars, instead of syncronising the subscription, as would be logical, the actual events are syncronised. And usernames of private calendars containing an @ symbol (ie. emails as usernames) are messed up – the @ symbol in the username gets confused with the @ used in http auth.

    Like many people before me, I’m sure, I’ve reported these as a bug yet nothing is done. One gets the feeling that .Mac syncing doesn’t have any internal resources allocated.

  18. Is your blog really the best forum for your beef with Apple? Did you traverse Apple’s knowledge, Usenet groups, the myriad enthusiast site discussion forums, et cetera? I’m not sure framing this as a ‘usability’ problem warrants space for this on your blog. It’s a technical support matter, one of a gazillion all computer users face at one time or another, PC and Mac alike. Were you merely trying to garner the collective wisdom of the crowd, venting or– worse–publicly shaming the OEM over something that may in fact be your own fault? (Not saying it is, but I’m just playing devil’s advocate here).

  19. Just upgrade both to Leopard you whinger!

    Thanks for contributing to the discussion.

    Do you always blame the customer when a product fails to live up to its promise? Or do you only blame the customer when it’s an Apple product?

    I love Apple’s products, too. I want Apple to continue to succeed. Bad customer experience that goes unfixed is bad for the customer, but it’s also bad for the company. It’s bad for any company, but it’s particularly bad for Apple — because significantly better than average experience is mainly what they’re selling.

    I reported these sync problems here because Apple doesn’t seem to pay attention to its own forums, where users report problems like this.

    It’s a usability problem because sync is advertised as something that just works.

    In practice, sync is buggy, and requires a certain amount of user knowledge. Apple could address the “user knowledge” problem by providing instructions, like other software and hardware companies do. Even just a page of information on its website — “do these steps in this sequence; don’t do such and such” — would go a long way.

    I’ve now got sync pretty much working between my home and office, and I’m able to sync my iPhone as well, and I’m no longer losing data every time I do this.

    The other thing needed to make it work is to sync only Calendars and Contacts on the Tiger machine. Nothing else!

    If I let .Mac sync Keychains and Bookmarks, the dreaded “ has been updated” loop begins, where the Mac informs me that a behind-the-scenes tool has been updated and asks if I want to allow the new version to access the same keychain items (such as passwords) as the previous version. If I say “Don’t change,” sync fails. If I say, “Change all,” sync also fails. But first, the machine freezes as all its memory gets sucked up in the futile attempt to update passwords — a process that should take almost no memory at all, and should happen in a moment.

    So by memorizing sequences and turning off defaults, I’ve got sync working. But it took some doing to figure out which steps to do in what order, and it took weeks of frustration with locked-up machines to figure out which parts of sync are broken, don’t work, never worked, can’t work (at least not between operating systems), and shouldn’t even be offered as an option, let alone a default, since all they do is break your heart.

    (And if I let .Mac sync mail preferences between my home and office machines, I stop being able to send mail from one or the other of those locations, since my home cable modem provider requires me to use their outgoing mail gateway even though I do not send mail from an account with them. That one’s not Apple’s fault.)

    Clearly, from comments on this page, many other users have simply given up because sync didn’t work for them at all. Those are customers Apple is losing to Google. It’s not in Apple’s interest to lose customers to Google.

    On its site, Apple provides sales copy about sync, and it provides a video about sync, but the video doesn’t show how to do sync — it just tells you how great sync is. It’s just a sales video. If sync isn’t working, and the only info you can find is an uninformative sales video — essentially a commercial for a product that isn’t working for you — you’re going to be frustrated. A frustrated customer is not in Apple’s interest.

    Since sync is supposed to “just work,” and since it’s a huge part of what Apple is selling with its $99/year .Mac accounts (syncing is the only reason I bought a .Mac account), it’s in Apple’s interest to fix the bugs and to provide simple “getting started” instructions on its website.

    I’m sorry it hurts you to hear that. Have a nice day, anyway.

Comments are closed.