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

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