Day One and Dropbox sitting in a tree


Day One and Dropbox together
When I first started journaling in Day One, I had to decide whether I should store my data in Dropbox or iCloud. Whilst my initial concern was that adding photos to Day One could eventually consume my iCloud storage space, I decided on iCloud as I’m trying to stay within the Apple ecosystem whenever possible.

That wasn’t the smartest decision.

Actually nothing seriously bad happened. The earth didn’t stop spinning, nor did a swarm of locusts invade my house. I did occasionally encounter sync issues where entries typed on my iPhone weren’t synced to my Mac, or vice versa. That isn’t a big deal, but it was irritating enough.

I decided to switch to Dropbox to sync Day One.

The switch

Switching to Dropbox on the iPhone was as easy as flicking the switch. Doing it on Mac was a slightly frustrating process, though. When trying to do it, Day One had multiple windows open at a time, and they kind of overlapped each other, making the process pretty irritating. I eventually got it working, but I seriously hope that the developers will make the process of switching easier on the Mac.

After switching, there were a few duplicate entries, but since there weren’t too many, I just manually deleted them.

The unexpected benefit

One of the reasons I selected iCloud as the storage for Day One was in the hopes that integration with Apple’s services would allow some form of background sync to happen, meaning that the App is always updated the moment I open it. Surprisingly, it didn’t work that way. When I opened Day One on my Mac, I would still need to wait a few seconds for it to sync before my entries from my iPhone would show up.

Using Dropbox as the storage medium, I realised that Dropbox would continuously be updated in the background, even when Day One wasn’t open. This meant that as long as my Dropbox folder is updated (and it always is), whenever I open Day One on my Mac, all my latest entries would be already available. This only seems to happen when updating the Mac app, though. I still have to wait for my iPhone app to sync. I guess it’s because iOS doesn’t allow Dropbox to sync in the background constantly, and I’ve turned on background sync in order to preserve battery life.


When you’re using Day One, use Dropbox to keep your data in sync. The developers behind Day One seem to indicate so too.


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