iCloud: It Just Doesn’t Work

The promise of Apple, for many of us, is a phrase we’ve all heard many times, “It Just Works.” It’s what we’ve come to expect from their products. They offer us not only an unmatched simplicity, but the confidence in the company to trust in that simplicity. For the most part, this holds true.

My iPod just worked. It’s what led me to buy my first iMac.

My iMac just worked, so I bought a MacBook Pro.

My MacBook Pro just worked, so when the iPhone was announced, I waited in line.

The iPhone just worked, so of course I went for the iPad when it was announced.

And since the iPad just worked, I decided to give iCloud a shot. A service that promised to be the thread between all of these devices. There’s just one small problem. It just doesn’t work.

I’m a big believer in Apple, I’d even go as far to call myself a fanboy. This is a company I want to give the benefit of the doubt to. Theirs is a vision of the future to which I am anxious to subscribe. They are a corporation that I would willingly trust and even pay to store my data. Unfortunately they just can’t seem to give me a service that delivers. As great as their devices are and as great as their software is, Apple has struggled with the cloud. Mobile Me was a nightmare from the start and while Apple seemed poised to redeem themselves with iCloud, it feels as if they’re dropping the ball.

Much like Siri, the few times that iCloud has failed on me has made me wary. Unlike Siri, Apple didn’t ship this as a beta. iCloud was billed their triumphant return to the cloud. Jobs himself acknowledged the shortcomings of Mobile Me during WWDC and promised us that, you guessed it, it would just work.

Well here’s an example of it not working. It a silly one, but it’s mine. I recently purchased Day One, a journaling program that I had just heard too much about not try. The application is available for my Mac and for my iOS devices and uses iCloud as a default to sync entries. It worked perfectly, for a day. Then it suddenly stopped syncing the data on my iPhone. I tried several things to get things going. I turned off the sync and turned it back on again. I even deleted the app from my iPhone and reinstalled it. I still ended up with one entry on the iPhone and multiple entries on my mac. I checked the folder names in iCloud, they were both correct:

Synchronizing Data Between Day One on the Mac and iOS

The data, not so much:

Day One and iOS Syncing Problems through iCloud

I even tried to access iCloud through the web to check the folder that’s referenced in Day One and realized that Apple doesn’t even allow users access to these folders:

No access to your folders on the iCloud Website

I only had one option left. Switch from the default option of iCloud to Dropbox. You know what happened? It just worked. Instantly. Even on Apple’s own device with every advantage imaginable, a competitors product worked better. I don’t know if the problem lies with Apple or Day One, I just know that since I switched over to Dropbox, a non-native competitor, things have synced up perfectly:

Syncing with Day One with Dropbox instead of iCloud. It just works.

It’s just an example, but you’ll find plenty of people with their own similar stories as to where they’ve found friction with iCloud and why they are now skeptical. The thing I really don’t get is why Apple decided to bite off so much at one time. By simultaneously launching iCloud for iTunes, Photo Stream, iWork and application syncing, as well as Me.com email, calendars and contacts it feels as if they almost set themselves up for failure. Why not go one at a time? I mean the Mac versions of iWork aren’t even compatible with it at the time of this writing.

Rather than go full steam ahead with all of the aspects of iCloud, Apple would have been far better off starting slow and building back the trust they had lost with Mobile Me. Much like the course I took with my devices, I likely would have followed a similar course with iCloud:

Start with iCloud for iTunes, give me my music, my TV and my Movies on all of my devices. Start with things I bought through iTunes and then go one step further and offer me even more with iTunes Match. Show me it just works.

Next add a photo stream that helps me seamlessly get pictures from my iPhone to all of my devices. I mean, how great would it be to have these all working perfectly with the ability to delete things at launch? Make it just work.

Then launch iCloud for iWork. Let me get familiar with how things work, let me see the benefit of not having access to a specific folder. Let me see that it just works.

Offer me the same option for the data for all of my apps. If it worked great for iWork, why wouldn’t it work well with everything else. You’ve already proved that it just works.

Last but not least, ask for my essential personal data. Everything else would have just worked, so why not this.

Would it have taken longer? Absolutely, but there would have been a far better chance that they could regain my trust. Now, there is little chance that I will ever trust iCloud with anything critical. It will remain my cloud for media, but will likely never be very much more. Apple has always been ambitious, but they almost always wait until something is ready to bring it to market. Everything isn’t always perfect, but it’s almost always ready. Twice now, we’ve seen that this is not the case when it comes to the cloud and I don’t see any reason to give them a third chance.

For a company that executed so well on a long term strategy to earn deep-rooted loyalty when it comes to our devices, it seems as if they either got impatient or cocky when it comes to our data.

It’s really a shame as I’d love to begin consolidating my various clouds. I currently have essential data in Google, Simplenote, Evernote, Dropbox, OmniFocus and keep my media in iCloud. While I like having my eggs in various baskets, this has gotten a bit unwieldy. At first, iCloud showed tremendous potential to help bring much of this data onto the same cloud. Even though there is a good chance that Apple will get their act together and make it so iCloud “just works” I think I’m finally at a point where I just don’t want to try anymore.

55 Responses to iCloud: It Just Doesn’t Work

    • It’s very likely, but the fact that nothing can be tweaked to fix it is an iCloud issue. The only way I was able to fix something was to change over to Dropbox. Once that happens its kind of crazy to switch back.

          •  So basically – you’re saying “no, I did not contact the maker of the problematic software”.

          • Partially. I’m also saying, if I can’t get under the hood, it’s unlikely I can fix my own car. Why contact the developer for something you usually wouldn’t need to contact the developer for.

            It’s obviously personal preference, but I am just not a fan of this strong a barrier between me and my data. In hindsight the piece was badly written. It focuses too much on the Day One issue (which was just meant to be a tangible example of what I believe the issues will be) and not enough on my concerns regarding iCloud.

    • I doubt this is DayOne only. I had major headaches getting my contacts synced up between my iPhone, iCloud, iPad and Lion. They are synced now, but I do not trust myself to update them anywhere. If I update on the iCloud site, none of my changes get synced. If I update on Address Book, some of my changes get synced. Only if I update on the iPad do all of my changes get synced.  And just today, I noticed that syncing on Notes just does not work… at all. I have tried every suggestion I could find in various forums and still no joy – I have my notes in Lion and on the iPad – but on the iPhone – nada. “It just doesn’t work” is a highly appropriate description.

  1. As far as I can tell, the only part of iCloud that gives people problems is the Application Sync (non-Apple). I wish they’d work on that more (and I do hope they are working on it).

  2. We’re very much of like mind, and I don’t like having my eggs cemented into a leaky basket.

    I do have a gmail account, of course, but I never use it directly. I have my other email addresses dumped into it as a backup, but I can still get messages on my server should Google go down.

    You’re dead on that Apple is missing an opportunity here, because most people aren’t as geeky as we are about building Robust Personal Information Systems. They would trust Apple to do it, with control of the chain from hardware to OS to cloud — if they could only get it right.

  3. It isn’t just DayOne with iCloud, have found it stopped syncing with other apps and will no longer do the overnight update either as the backup takes up all the space with no photostream or iWork’s synced. Dropbox FTW!

  4. Well you said it man. iCloud worked perfectly for me…and then one day, everything went to shit. When I had to restore to a new device from the genius bar (don’t even get me started on their refurbished “factory new” phones – of which I went through about 7 or 8 of them) I could not restore from any of my iCloud backups. They showed up on my iCloud account, they showed up on apple’s back end, but when restoring a new device (heh, “new”) the backups that we could see in both places seemed non existent. This was the first anomaly that the geniuses, the apple care reps, and engineers had never seen before. Then, while still dealing with transferring over to a new device, it suddenly became impossible to START a new backup. The wheel spins overnight with no progress saying “estimating time remaining…” So now I have to stick with iTunes backup. Apple is unable to find a solution and will probably assume there must be something wrong with me or my story isn’t true. But the fact of the matter is, my iCloud has died and gone to apple heaven. I will never use it again. And apple has no Idea what went wrong. A shame indeed. We need jobs back.

  5. My iCloud died this morning.  I have no idea what happened.  It won’t speak to me.  At all.  I am going to have to brave the Apple store where, because I am female, blonde and aged over 40 I will first have to persuade them that it is not my fault (it has been working OK for months – although I gave up on using it to transfer files .. Dropbox definitely works better!). Then I will have to put up with them giving me the run around because, I suspect, they won’t know why it is dead either.  I love my Apple stuff but it is definitely letting me down.

  6. It is very sad and frustrating. iCloud has never worked for me with anything – not iCal, not the address book, not anything. What makes it worse is that I live and work overseas so when I was back in the US trying to get this all sorted, if they had just been honest and told me it doesn’t really work, I wouldn’t have wasted so much time trying to figure it out.

  7. My #1 message everyday (below)

    Ring Ring Ring Apple, 1994 called and they want to teach you about EMAIL!  It’s a glorious invention that’s reshaping the world.  Maybe you should google or yahoo it?

    • Dropbox is a shared folder that works across several devices. It would not replace things like Photo Stream, but I do find it to be a better, more accessible method of storing files.

  8. Great writeup Michael. In ancient times (when you wrote this piece – back in March lol) I could have passed off your frustrations for a relatively new icloud experience that just needed a few bugs worked out. I’m in that realm of emerging believers, gradually and assuredly migrating from windows to ios, but today I am stalled! After a rocky start with syncing my windows pc to the icloud and my iphone and ipad – I lost all my data and had to rebuild contacts files with over 6000 contacts. After dedicating (a kinder gentler way of saying “being robbed of”) scores of hours rebuilding files, I was finally able to successfully sync! Huge high. The euphoria lasted a week. Huge low. Sync no longer works; the techs want to turn everything off, delete all the data and try rebuilding from backups…again! Why don’t we just go to the old default solution “turn it off and turn it back on and see if that works”? I’m thinking about hitting the side of my router…

    • Thanks, when I first wrote this piece, I shifted the emphasis far too strongly onto the Day One issue (which I was just trying to use as a tangible example). My concerns of not being able to get at the information isn’t something that’s going to go away anytime soon. Merlin Mann has had some really interesting and salient points on this lately. Apple so desperately wants to make this easy for the average consumer, but that ease is adding so much complexity.

      I just don’t have the time to use something I can’t see. I’d rather stick with my current sync options and only use iCloud where required. If things change, I’m sure I will as well, but for now, it just doesn’t work and there are other, more complicated options that do.

  9. I totally agree. I’ve been an apple user for more than 10 years and since they decided to get popular and easy to the average user things started to crash. In the past I trusted my mac and apple softwares, but now… It seems the need to launch a new os, a new device, a new service every year is surpassing the need of doing things work, or at least work better than the competitors. Mountain Lion is full of bugs, iCloud does not work. I’ve lost data more than one time and yesterday my iPad stopped syncing with icloud. I’ve tried even a restore to factory settings without success. My other devices is still working… I’ve lost much more time trying to fix iCloud messes than it has helped me with my work/life. If things continue this way I’ll no be surprised with a leak of iCloud users data on the net… A fell from the heart Apple is leading itself to dark ages. The bottom line, do not use iCloud! at least for critical data.

    • I’m hopeful they will get this figured out (and thankfully have not been having issues with ML), but for now, it’s just not something I’m ready to trust with anything essential.

  10. I have had many issues with icloud especially trying to sync my calendar across devices. When mobileme first started it was able to sync my calendar to all my devices (iphone, ipad, mackair and outlook on one pc). There was only one main calendar and i was able to accept meeting makers fine. Then they did the so-called calendar “upgrade” and suddenly it created 5 separate calendars, I could only accept meeting makers into the main outlook calendar on my pc which is the only calendar that won’t sync anymore. I now have to make multiple entries in several calendars to get events to show up on all my devices and it also will no longer support reminder alerts. I called tech support and was told basically too bad, we don’t really care if it doesn’t accept meeting makers from outlook (which is what all my clients use) and that they couldn’t talk to me about it anymore unless I paid for their time because I didn’t have a current service agreement. Needless to say, I am disappointed and now annoyed with apple. I had planned to totally switch to mac/apple but have now decided to stick with pc and am waiting for windows 8 which is supposed to be a whole lot better but seems to be taking ages to be released! I really don’t understand why they would have such poor customer service and why this program is so bad.

  11. I wish I’d read this before I backuped up and reinstalled (on my computer). iCloud is working for Notes, Reminders etc. but not for the Calendar which, of course, is what I really need. Now after reinstalling the backup from my computer, there are tons of entries missing. Any suggestions on a calendar app that will work through dropbox? It may be worth paying for.

  12. It´s such a crap, i can´t believe. How much time I had to waste just to get things back. My mistake was, to install Mountain Lion and buy a new iOS device. Fortunately i could restore most items from my old iPod Touch. Just lost 6 weeks.

  13. I recently switched back to Apple from Android and have found the iCloud to be pretty useless. It is inconsistent at best. Photo Stream via iCloud only backs up about half of my pictures, same with my contacts. Pretty disappointed overall. I am now manually backing things up.

  14. I can’t stand the fact that no matter what I do I cannot get iCloud to sync my work and home calenders. The majority of the time, I end up with nothing on the calender. What a waste of time I’ve spent on this. The thing is I have a hectic schedule and I need my calender on my iPhone so I know where I need to be. It hasn’t worked well since I got my phone. Just the most frustrating thing ever. I love my phone but iCloud is horrible. Please get that fixed.

  15. I found your article after having the same issues with Day One and iCloud. I thought I just didn’t understand how to use iCloud and wasted hours looking for help. Thank you for the article, I signed up for Dropbox and the Day One files were on my computer in minutes. I can’t believe I wasted so much time with iCloud, there is no way to access folders if you have a PC and they don’t tell you that anywhere.

  16. I’ve been back and forth with iCloud for about a month and thought I had finally nailed it. I was wrong. My iPhone and iPad sync, but only with each other, neither with my computer. I’m now trying a Microsoft service.

  17. I’m pretty disgruntled too. Early on the cloud showed me my purchased movie and tv library on my laptop, and I could stream it and save time and drive space…. Now it’s disappeared, and only works with the music… Sucks, sucks, sucks!! Still works on Apple TV, we have 4 or the current generation ones in the house, but no longer available on our MacBook Pros. The larger my Apple ecosystem has gotten the more problems that I have with things not working…… Apple is becoming the “new” Microsoft. Oh yes, and “one more thing,” my “me.com” account won’t work in the new iCloud… so much for backward compatibility. Apple genius’s tell me that I can’t merge my original apple store account that predates MobileMe, with my me.com account, and now my me.com account doesn’t fit the iCloud paradigm. So much for backward compatibility.

  18. Spot on – I had the same issue with Day One – iphone entries won’t sync – and the same issue with pages as the iphone app won’t download any entries from the iPad – utterly useless. However so incompetent is icloud that when I try to disable it from Day One – it crashes the app. So I am finished with icloud, and since that is at the core of iwork – it renders iwork pretty well useless as well unless you want to email your docs back and forth all the time. I’ll be using ‘docs to go instead’. Sorry apple you’re killing yourself and you don’t even know it (long time apple fanboy)

  19. Yeah, it’s astounding (at first sight) how even the most simple of tasks, like syncing Reminders, doesn’t work reliably or at all (much of the time, the app either crashes when syncing, or it takes MINUTES (!) to sync a few KILOBYTES of data).

    However, having used ObjectiveC and various Apple APIs, I think their general problem is this: Over-engineering. ObjectiveC is over-engineered. Their iCloud API is over-engineered. Everything is over-engineered.

    Mind you, Apple is trying to achieve noble goals with this, namely avoiding UNDER-engineering, like Android. Because that’s even worse.

    Something in the middle would be great :-)

  20. I’ve rolled my own app just to get rid of iCloud Reminders, and while I’m totally happy with that, it’s still totally impossible to get rid of iCloud Reminders, as it won’t let me delete the iCloud Reminders Lists, and turning off Reminders in iCloud settings has no effect (other than appearently putting ALL ex-iCloud-Reminders from ALL lists into a SINGLE local list “Reminders”, IGNORING the “Completed” flags. WTF!)

  21. I can’t use this iCloud garbage. When I bought my iPhone 4S I had trouble getting my contacts synced. Eventually I managed to get it to work when I reset the sync option. My contacts were updating but my other information wasn’t. After some time, I noticed that my contacts weren’t updating anymore and nothing was updating PERIOD. I was on the phone with tech support for two hours and the final solution was to do a hard restart on the phone but she needed me near my MacBook Pro for that. At that point I gave up and downloaded Verizons Back Up assistant for my contacts, my emails are Gmail so I wouldn’t lose those, and everything else like my photos I can just take them as a minor loss.The only thing I use iCloud for is for the Find my Iphone app. But that’s the only thing it’s useful for.

  22. I have never had an Apple before. After all the hype I cautiously bought a Mini Mac to see how Apple compared to PC computers.

    It came without a handbook, so I had to guess how anything and everything actually worked. I can use it only for e-mail, news, and Facebook.

    Security apparently doesn’t allow it to play IPlayer (BBC radio) or any radio station. There are no instructions and there is no support. I cannot record anything or store my own music files, or access music.

    Does Apple want to turn away new users. Does it care about its reputation? Does it think it is too big to fail. I am disgusted with the total lack of support or instructions.

    I have browsed all kinds of questions on Safari to overcome this dilemma but can find no clear or comprehensible answers. If Apple wants a detractor I am ready to fulfill that need, and get a discussion going about Apple computers, or maybe they will care a damn and let me know how this frustrating machine works, and how to get it to do ANYTHING outside of Mail and Facebook.

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