Move Day One Journal From iCloud to Dropbox

Let’s face it: iCloud still has some way to go before it will become stable and reliable. At the moment, it toggles between working not at all and “meh” at best. Admittedly, it works okay-ish for Apple’s own applications.

I have been hit by the issues with iCloud after i gave it a spin for my Day One journal. For some time, it worked to some extend, slow and unreliable but eventually I got my content synced across devices (even if this involved restarting my iOS device).

The last two weeks, however, made me wish I had never been so reckless to move the journal away from Dropbox to iCloud. Consequently, I arrived at a point where I decided reverting the move and migrate my stuff back to Dropbox.

This turned out very cumbersome because, for being able to migrate to Dropbox, you need to tell Day One to stop syncing with iCloud in the first place. But: how can you do this if iCloud has reached a level of unreliability where it would not even respond to a request to stop working?

I tried everything from restarting Day One, to waiting for 15 minutes and see whether it would respond eventually, to deleting the app and reinstalling it from the App Store. Alas, it all failed.

Eventually, I successfully ended up telling iCloud to stop syncing in a way that was mostly unexpected and, frankly, quite unintuitive. Here’s what worked for me:

  • Put iOS device in airplane mode
  • Reboot iOS device
  • Launch Day One
  • Go to the sync preferences
  • Deactivate iCloud (this time it will not stall somewhere in between)
  • Activate Dropbox sync