Day One 2 journal app loses iCloud and DropBox syncing

Day One has long been regarded as one of the best journaling apps around. Many people use it each day to write about what’s going on in their lives. Day One has proven to be quite popular among iOS and OS X users, and now there’s an entirely new version of it called Day One 2.

Since Apple still doesn’t offer upgrade pricing, the Day One developers have opted to create Day One 2 and have dubbed the first version Day One Classic. Don’t let the naming confuse you, Day One 2 offers much more than Day One Classic. You can read the Day One 2 announcement by the developers for much more detail about the new version.

I’ll share my thoughts below, but here’s a quick list of What’s new in the Mac version of Day One 2: – All-new user interface – Multiple Photos per entry (up to ten inline photos) – Multiple Journals (up to ten journals with unique colors and names) – Day One Sync 2.0 – Photo View – Custom Reminders – Entry Management (select, move, tag, and delete multiple entries at a time) – Timeline Filters (star, tags, location, year, activity, and music) – Timezone Support – Multiple Window support – Single and Dual Pane Modes – Redesigned PDF export – Gesture support Other Features: – Automatic metadata (location, weather, motion activity, step count, and music) – Search – Tags and Stars – Export to PDF with smart filters – Share Extension – Shortcut keys

And here’s a quick list of what’s new in the iOS version of Day One 2:

– Multiple Photos per entry (up to ten inline photos) – Multiple Journals (up to ten journals with unique colors and names) – Day One Sync 2.0 – Map View – Custom Reminders – Entry Management (select, move, tag, and delete multiple entries at a time) – Timeline Filters (star, tags, location, year, activity, and music) – Timezone Support – 3D Touch – Local, Exportable Backups Other Features: – Passcode Lock with Touch ID – Automatic metadata (location, weather, motion activity, step count, and music) – Apple Watch App – Search – Tags and Stars – Export to PDF with smart filters – Today Extension – Share Extension – Export to PDF and plain text

Obviously there’s some feature overlap between the Mac and iOS versions, but the iOS app does contain some things such as 3D Touch that are unique to mobile devices. I think it’s worth it to buy the Mac and iOS versions if you want to sync your journals across all of your Apple devices.

The standout features here for me though are the ability to use multiple journals and multiple photos. Many Day One users have been asking for them and now they are finally here.

I bought Day One 2 for iOS and OS X and then deleted it

I had no problems with the pricing of Day One 2, so I bought the iOS and Mac versions right away. I was happy to support the company that makes Day One, because I hadn’t given them any revenue since I bought the original app years ago.

And I also liked the new features, they’ve clearly done a great job on it. There’s quite a lot to love, and very little to dislike…except for one thing. I did not feel comfortable using Day One Sync for my journal data.

At this point I only trust Apple’s iCloud for that kind of data. That’s not a knock on the folks that make Day One, it’s just that I know exactly what I am dealing with with Apple. So I’m more comfortable using iCloud to sync my journal.

Unfortunately, iCloud (and DropBox) syncing is not included in Day One 2. So if you want to sync your journals across your Mac and iOS devices, you must use Day One Sync. And right now that’s a bridge too far for me, so I’ll be sticking with Day One Classic. It’s definitely a bit of a bummer as I like Day One 2 a lot, but I just don’t feel comfortable using Day One Sync.

So I’ve already deleted Day One 2 from my Mac, iPhone and iPad. I still have Day One Classic installed though and I’ll continue using that each day as I have for years.

I emailed the Day One developers about this and got a nice reply back that promises stronger encryption in version 2.1 of Day One 2:

We really appreciate you supporting us by purchasing Day One 2. Have you read our Day One 2 FAQ about why we created Day One Sync: http://help.dayoneapp.com/day-one-2-0-faq/

As far as security, in its currently available form, Day One Sync encrypts the data “at rest” on our servers and securely transfers the data from our servers to the Day One app (the same level of security that Dropbox and iCloud provide). Following our 2.0 release, our 2.1 update will provide full private-key encryption on the server. Our encryption features will utilize the user’s private key to encrypt all entries before they reach the server.

In short, the server will have no access to the user’s unencrypted data. Neither iCloud nor Dropbox currently provide this level of security (see: https://support.apple.com/en-us/HT202303 and https://www.dropbox.com/help/28, respectively), thus making Day One Sync even more secure than these other sync/backup methods.

So it seems that the Day One 2 developers are aware that syncing security might be an issue for a certain number of their customers. I’ll take another look at Day One 2 when the 2.1 version comes out. But for now I’ll stick with my trusty Day One Classic app, it doesn’t have all the bells and whistles of Day One 2 but it still works fine and it’s still a great journaling app in its own right.

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