iCloud Catastrophe

When the new photo app dropped, I decided to try out the iCloud photo library. This meant upgrading my iCloud storage so it could hold my photos. I had just enough photos to blow the cap on the 99¢ tier and had to go up a step, which left me with plenty of extra space to use as a synch store.

I’ve used Dropbox for years happily but have recently been bumping up against my storage limit. Since photos required iCloud but my dropbox files could sit in either service (and I have good backups both Time Machine and manual), I decided to give iCloud drive a try.


Dropbox syncs quickly and reliably, and I went about my work as if this would be the case with iCloud (after a couple hesitant hyper-vigilant days of checking the Finder to make sure everything was working as it should). Unfortunately–and I’m not sure what’s going on exactly–iCloud doesn’t sync immediately after a file saves or closes, or at least it doesn’t do so consistently.

So over the course of about four days, I worked on what I thought was a synced version of a single file on my iMac and my MBAir. What was in fact happening was that I was working on two different files that were only occasionally syncing. And because I was entering notes into a very large Tinderbox file I was doing nothing that would clue me in to the problem: no revision, no review, just entering data in one note, then entering data in the next.

Once I realized there was a problem, I began to poke around and realized that, even after my computer had been on for 10-15 minutes, there was no guarantee that any particular file had synced to the latest version. (Although opening a finder window to a folder seemed to push the files in that folder to sync immediately. Usually.)

Conflicts? What Conflicts?

It gets worse: iCloud never asked me to resolve conflicts between the versions of the file I was working on. Instead, it simply replaced all copies of the file with the latest version. In practical terms, this means I could enter 50 notes on my desktop, close the file and do other things, then later that day open the file on my laptop (it would appear to be synced but would not be), add a note or two and close the file, and then the next morning when my desktop synced, the laptop file that added two notes would replace the desktop file that added 50. And all of this with no warning or prompt.

Yet, I know that iCloud was registering conflicts because when I went to delete the ruined file, the system blocked me with an alert window that said the file had unresolved conflicts and could not be deleted. I went through every option I could find to figure out how to resolve (or even see!) these conflicts, but no luck.

Not that it would have mattered: the haphazard syncing over several days had riddled my Tinderbox File with holes and populated my backups with conflicting files that I couldn’t easily sort through or draw from to fix things. In the end, I had to print out the outline of my Tinderbox and painstakingly go through it line by line to figure out what I had and what was gone in order to know what to reenter. It was frustrating beyond description.


So I’m now very leery of iCloud. The integration is really appealing but I can’t account for the sync behaviour I’m seeing and so can’t adapt to it. This is a problem.

My files are important, and I hate hate hate having to do work twice because something messed them up. This has to happen to me only once and suddenly I have real trust issues.

So for now, my files are back in Dropbox, where they’ve been for years, and I’ve pulled my photos off the cloud (because the photo sync alone isn’t worth the storage cost).

That said, I like the idea of iCloud…so here’s hoping things improve.


Wallace Steven–Poetry Is a Destructive Force

Poetry is a Destructive Force

That’s what misery is,
Nothing to have at heart.
It is to have or nothing.

It is a thing to have,
A lion, an ox in his breast,
To feel it breathing there.

Corazon, stout dog,
Young ox, bow-legged bear,
He tastes its blood, not spit.

He is like a man
In the body of a violent beast.
Its muscles are his own . . .

The lion sleeps in the sun.
Its nose is on its paws.
It can kill a man.

—Wallace Stevens