Under The Microscope

User Hostile Experiences

Recently, Fraser Speirs tweeted about some lousy behavior from the current version of Apple’s iWork suite. If you attempt to use iWork 2013 or later to open a file created by iWork ’08 or earlier, you’ll get an error. Apparently the file has gone stale, and possibly moldy. It’s “too old” to be opened by the current iWork, and must first be opened and re-saved with iWork ’09.

This presentation can't be opened because it's too old. To open it, save it with Keynote ’09 first

This makes for quite a lousy experience. At best, you need to use a second application to manually do something that the software should instantly and automatically handle for you. Worse, if you don’t have iWork ’09, you could be entirely out of luck in opening a document that may be just a few years old.

That’s troubling, and it’s not the only crime of which iWork is guilty. Fraser’s tweet reminded me of several gripes I’ve recently had with iWork, so I decided to detail them.

OS Upgrades Are Still a Big Deal

In 2011, Apple greatly simplified the installation of operating system upgrades. With the release of Mac OS X 10.7 (Lion), major OS upgrades could be purchased via the Mac App Store. Two years later, with Mac OS X 10.9 (Mavericks), Apple made their OS upgrades free. It’s now possible to trigger an upgrade to your OS with just a few clicks, and at no cost.

However, while the logistical and financial barriers have now been removed, the technological changes found in any major operating system upgrade are as real as ever. Upgrading your OS still makes major changes under the hood which can have far-reaching impact. Users with a functioning workflow have always been wise to take a cautious path when it comes to OS upgrades, and that remains true.

And yet, frequently when I open an iWork app on a Mavericks machine, I’m greeted by this message:

Install the latest version of OS X, then visit the Mac App Store to download the latest version of Keynote.

Suggesting that users upgrade, when their current OS doesn’t support the new version, is just irksome. Wait until they’re on the new operating system, then pitch the upgrade.

Similarly frustrating is this dialog, which appears every time an iWork app is launched on Mavericks:

iCloud Drive isn't compatible with OS X Mavericks.

These dialogs both pretend that an OS upgrade is no big deal. That’s a grave disservice to users whose workflows are very likely to be disrupted in some fashion with the OS upgrade. To top it off, they fail to offer a “Don’t Show Again” checkbox. They never stop appearing, until you finally do upgrade your OS.

Opening Yosemite Files on Mavericks

While the above dialogs are obnoxious, they’re at least accurate. An OS upgrade is indeed required to use the very latest iWork app versions, or iCloud Drive. More recently, I’ve run up against a problem which claims to require an OS upgrade, despite the fact that one is not actually required. I’m detailing the workaround here, in the hopes that others can find it.

If you create a document in the latest iWork apps on Mac OS X 10.10 (Yosemite), and then attempt to open it in the latest iWork apps on Mac OS X 10.9 (Mavericks), you’ll get this error:

iCloud Drive isn't compatible with OS X Mavericks.

Earlier, we saw that the iWork team was willing to treat files that were current as little as five years ago as “too old”. Now, it seems that a file made just six months ago may require the very newest OS to be opened! While griping about this to a friend, he sought out someone he knew on the iWork team, who was able to provide a workaround to the problem.

It turns out this dialog is somewhat misleading. While that particular copy of the file can’t be opened on Mavericks, it is possible for the iWork apps on Yosemite to create files which are compatible with both OSes. To do so, you’ll need to go to the “File” menu, then selected ”Advanced”, then “Change File Type”. On Yosemite, this defaults to “Single File”. Switch this to “Package” and re-save. The file will now be openable on Mavericks as well.

iCloud Drive isn't compatible with OS X Mavericks.

This option is not available on the initial save, so you need to first save, then change the file type and re-save. It’s also tremendously well-hidden. In my case, finding it required the indirect help of an actual iWork engineer. Hopefully, future users who run into issues opening an iWork file from 10.10 on 10.9 will find this post and the workaround.


Ultimately, none of this should be necessary. When a file is “too old”, the software should contain the necessary code to update it, without requiring another app to act as intermediary. When an update requires a new OS, it shouldn’t be mentioned to users, and certainly not repeatedly. File compatibility between versions should be maintained for years, even decades, rather than being lost in a matter of months.

The above problems all result from poor product management. Decision makers either didn’t consider people not running the very latest versions, or worse, they just didn’t care about them. Users should never have to worry that their data will be unavailable to them, particularly when it comes to productivity apps. Unfortunately, rather than providing a user friendly experience, iWork is currently outright hostile to its users.

I hope we’ll see improvements in the future. To that end, I have indeed filed some radars.

rdar://20325798 – Files Should Never Be “Too Old”

rdar://20325848 – Enough About the OS Update

rdar://20325823 – Enough with iCloud Drive Already

rdar://20325881 – iWork Files From Yosemite Can’t Be Opened on Mavericks, by Default

10 Responses to “User Hostile Experiences”

  1. The_Lone_Beagle says:

    You are emailing this to Tim Cook, right?

    You’ve hit the nail on the head, and I’ve had the exact same experiences you’ve had.

    Add to that, the frustration of new OS releases *every* year, combined with their lack of support for OS’s more than 1 gen back, and if you have a good workflow, it will undoubtedly be disrupted.

    This is not why we choose to use Mac’s.

  2. ViewRoyal says:

    Paul, I do agree that the problem you outlined in the article is bothersome, but on the other hand I try to face these types of things realistically.

    If I had a file that I hadn’t updated in 7 years, and then found out that it didn’t open easily in a current version of the application, but had to do some work to get it open, I would not be too put off by it.

    These types of situations always crop up with all out of dat applications, NO MATTER WHO the developer is.

    At least that 7 year old file is salvageable, and Apple is still making a newer version of the originating application.

    Things could be A LOT worse, if you have an old file, and the application that created it is no longer available.

    I have some beautiful Hypercard files that I worked on, but Hypercard app is long dead. There is no way to open those files (there are some expensive third-party apps that claim to open them, but I have not heard good reviews of them).

    Operating systems, apps, and technologies in general change over the years. We either learn to live with and accept that reality, or we can decide to suffer over it.

  3. MudMan says:

    Great article! I experienced two of the four issues above when I was on Mavericks and was debating whether to move to Yosemite… Those popup messages annoyed me enough that I moved one of my MacBooks to Yosemite. It is a good thing that I left my other Macbook alone – the one that I use for my consulting work…

    And thanks for the tip about “saving as package” – now, I can save my iWork files so I can at least open them on my not-so-old-but-ancient-in-apples-view Mavericks OS :)

  4. Doug Grinbergs says:

    Thanks for highlighting these various annoyances! I strongly agree that it’s poor product management; bad for the Apple brand, *especially* among its dedicated, long-time users. (:-( Even if the latest apps didn’t support legacy file formats (come on, Apple, how much app overhead versus how much user time and goodwill wasted on screwing around manually reformatting files?), there could be a drag-and-drop batch-update (AppleScript/Automator) utility to manually convert files (with helpful option to keep original file timestamps).

  5. Edmond says:

    iPhoto recently became incompatible with iOS 8. It just wouldn’t open. I think I actually paid for this a couple of years ago.

  6. John says:

    Whole heartedly agree. This sums up everything that is currently wrong with Apple’s various software offerings. I think the yearly upgrades have become a rod for their own back, with Yosemite / iOS8 being prime examples of things being rushed ( app UI inconsistency on the 6+, discoveryd flakiness on all Macs ), and despite the huge workforce, other areas of the product line, hardware and software, are being ignored ( anyone that says the ATV isn’t only needs to use it with a large library to see the errors of their ways; the iPad is no better state, and where is the feature parity with iWork iOS / Mac? ). The Watch is only going to add to these issues.

    Gone are the days of It Just Works(™), seems to be now Only Just Works.

  7. Joshua Nozzi says:

    I’ve found myself yelling at my Mac and iOS devices a LOT lately for really stupid things. I’m sad to say I’m hard-pressed to find much good to say about either lately, considering the apparent decline in overall user experience.

    I just spent the morning fighting HARD with Mail.app to show me the correct content for a selected mail folder (some smart, some server-hosted, none actually working correctly) and a “rebuild mailbox” did nothing for any.

    Apple is quickly becoming another Microsoft in my mind and that terrifies me.

  8. Doug Grinbergs says:

    Thanks, too, for taking the time to file and share your radar (Apple bug) reports. (:-) Any number of Apple internal developers, user experience evangelists could also do/have done this.

  9. Steve Nicholson says:

    I tried to open some Pages files that I created when we first bought our veterinary clinic in 2008 and ran into the “too old” issue. Luckily I still have Pages ’09 so I could open them. Ironically, the same version of Pages that can’t open old Pages files has no problem opening .doc files from the same era.

    It would be easier to work around this if there was a way to search for Pages files that will open in Pages ’09 but not Mavericks’ Pages. But I’ve examined the files with HoudahSpot and the Content Kind and Content Type don’t seem to have changed. So I guess the only thing to do is look for Pages files with a modification date before some unknown cutoff.

    And don’t get me started on AirPort Utility 5.6 not running under Mavericks. AirPort Utility 6 won’t configure older Airport Expresses, which are perfectly serviceable AirFoil destinations that I have in my bedroom, garage, and back deck. So if I need to reconfigure one I have to find a 10.8 boot disk.

  10. deblooze says:

    This reply is specific to Steve Nicholson’s Airport Utility problem:

    Go to the following site and download “AirPort Utility v5.6.1 Launcher.app”. It has worked like a charm for me on both Mavericks and Yosemite, allowing me to continue using my original 802.11g Airport Express units.


    It does not interfere with the operation of Airport Utility 6.3.4, which is still necessary to configure the newer Airports.


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