I’ve had only a few moments to explore iOS 8, and attempt some of the sharing possible with Mac OS X Yosemite, but what I’ve seen so far is very tantalizing. But the Mac technorati are howling about the version skew problem with the new version of iCloud, and the sync capability called iCloud Drive. In a nutshell, the problem is this: for those who depend on the old generation of iCloud to sync between Mac OS X and iOS, upgrading only to iOS 8 basically breaks the sync. Most people haven’t upgraded to Mac OS X Yosemite — which is only in beta — so if they upgrade to iCloud Drive on their iPhone or iPad they will be out of sync until upgrading to Yosemite. This doesn’t only impact Apple’s apps, since there are many other apps that use iCloud to sync data across devices.

However, I am running Yosemite on my MacBook Air, so I have been poking around.

I have not been able to get the Continuity service working, but that’s because my iPhone 4S doesn’t have the chipset to support Bluetooth LE, something essential for the iPhone-based Continuity features to work. I’ll just have to wait for for my iPhone 6+ to arrive from AT&T, or borrow an iOS 8 enabled iPhone 5.

What I have been trying out is the new iCloud Drive, which is the successor to the flawed iCloud of iOS 7.

iCloud Drive is a file sync service intended to sync files across devices running iOS and Mac OS X, and to other platforms through iCloud apps. The operation is much like the sync capabilities of Dropbox, but on iOS 8 and Mac OS X does not require an app: it’s working at the operating system level.

Here I have created a folder called AdjectiveNoun and uploaded an image there through the web interface:

Note that documents cannot be edited there, even native Apple files like Pages documents.

On my Mac, the iCloud folder is found in the Finder Favorites sidebar. When opened, this is what is shown:

I created a Pages document, called ‘in Ohare.pages’ which is where I am writing this. The image has not synchronized — note the cloud icon representing that state. My hypothesis is that iCloud Drive is delaying sync until I have higher bandwidth — I am currently using my tethered iPhone as Internet connection. (Update: confirmed.)

Note that I created a Pages document there, called ‘in Ohare.pages’, after O’Hare airport and if I descend into the Pages folder, the document appears linked via a Mac OS X alias:

But that alias does not appear on my iPad.  Here’s how Pages on the iPad accesses that files, and there doesn’t seem to be a way to get up out of the iCloud Page folder on the iPad in Pages, so I can’t edit the Ohare.pages document in either folder on my iPad. A real design mess, and one which I had hoped they’d fix before this point.

At the present time, I think iCloud is only slightly better that the iOS 7 version, and is still stuck in the ‘Pages folder for Pages documents’ siloed style of use, and not the more general folder model that we are used to on Mac OS X. Until that is settled, I can’t imagine replacing Google Drive or Dropbox as my mechanism for syncing across my devices.

What else is missing? There does not seem to be a means to share a folder with another person or group, which makes iCloud strictly a personal tool. You can share a file, but that’s the wrong granularity for work.

This is no Dropbox killer, Apple.

In related news, the fallout of the departure of Brad Garlinghouse from Hightail has led the founder and now-CEO, Ranjith Kumaran, to cut the staff by half — 100 people — according to Arik Hesseldahl at Re/code/. More proof of consolidation in that market.