Day One Journaling App Gains End-to-End Encryption Feature

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Popular journaling app Day One received an update yesterday that introduces end-to-end encryption to its cloud server for the first time, as well as a handful of other improvements.

Rather than using iCloud, Day One synchronizes data between devices using its own servers, something that has opened it up to criticism in the past because of security concerns regarding private journal data.


Version 2.2 of the app should allay those worries, since Day One now encrypts journal data from client to server via a user-generated private key. However it's important to note that the new end-to-end encryption feature is enabled on a journal-by-journal basis, so users need to go to Journals in Day One's Settings and select the journals they want to encrypt from there.

If users do not enable end-to-end encryption, Day One defaults to standard encryption, which encrypts journal data "at rest" on the company's servers. This less secure method requires that Day One staff hold the keys to decrypt journal data.

In addition to the enhanced security feature, the in-app camera has been improved to make it easier to take photos and quickly add multiple square-cropped shots to entries. Journal metadata now also includes the device name on which an entry was created.

Elsewhere, recent searches are now saved in a list for convenient re-use, while an app-wide state restoration system has been implemented so that users can pick up where they left off in the event of a crash or a force quit. The update also includes several fixes that should improve the user experience.

End-to-end encryption is included in the 2.2 update for both iOS and Mac. Day One is a $4.99 app on the iOS App Store and costs $39.99 on the Mac App Store.

Article Link: Day One Journaling App Gains End-to-End Encryption Feature
 
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iDento

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I've been using this app for 7 years and it's really useful, although when they released ver 2.0 I bought the iOS app only, partly because I don't use my Mac for this kind of apps anymore and partly because it is expensive, I got version 1 for 19.99$ if I am not mistaken.

End to end encryption and a solid sync are major features and they're nailing it.
 

GrumpyMom

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Sep 11, 2014
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I've been using this app for 7 years and it's really useful, although when they released ver 2.0 I bought the iOS app only, partly because I don't use my Mac for this kind of apps anymore and partly because it is expensive, I got version 1 for 19.99$ if I am not mistaken.

End to end encryption and a solid sync are major features and they're nailing it.
If they ever go out of business or stop making this app, is there any way to move all of your entries to something else?

The last time I attempted to keep anything like a journal was a notebook in college. Electronically I used a Word document but got tired of that after a week's worth of entries. Facebook was fun but obviously I can't write anything too private on there.

I'm 50 and while I don't need to pour my heart out into a diary I do need some way of remembering what happened last week. I meet a lot of people and forget who they are fifteen minutes later. It would be nice to have a journal to help refresh my memory about such things. I kind of survive off of post it notes. Or worse, I email myself. Doh.
 

jarred125

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This is how encryption should be! Only YOU should have access to YOUR data!
There is always a trade-off, either its easier to use (iMessage) or hard because you have to manage the key exchange. For this app it's a no-brainer, but for iMessage would you really want to have to exchange encryption keys with each person you wanted to communicate with? That kind of security is likely not required on a day to day basis for the vast majority of us and I prefer the easier to use methods for that, but there are some nice options for when you really need to ensure security but again, it's not "easy".
 

iDento

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Sep 8, 2011
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If they ever go out of business or stop making this app, is there any way to move all of your entries to something else?

The last time I attempted to keep anything like a journal was a notebook in college. Electronically I used a Word document but got tired of that after a week's worth of entries. Facebook was fun but obviously I can't write anything too private on there.

I'm 50 and while I don't need to pour my heart out into a diary I do need some way of remembering what happened last week. I meet a lot of people and forget who they are fifteen minutes later. It would be nice to have a journal to help refresh my memory about such things. I kind of survive off of post it notes. Or worse, I email myself. Doh.
I export my entires as PDF files each month, then use an app to hide it, I use Hider 2 for that.

The PDF files exported by DayOne looks gorgeous and frankly, I think they look even better than viewing my journal in the app interface!

Also, you can order prints of your data but I'm not quite familiar with that.
 

Rigby

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There is always a trade-off, either its easier to use (iMessage) or hard because you have to manage the key exchange. For this app it's a no-brainer, but for iMessage would you really want to have to exchange encryption keys with each person you wanted to communicate with? That kind of security is likely not required on a day to day basis for the vast majority of us and I prefer the easier to use methods for that, but there are some nice options for when you really need to ensure security but again, it's not "easy".
There is really no contradiction. The only thing missing in iMessage to provide full security is a way to verify the identity of the peers when needed, e.g. using a fingerprint of their public keys (similar to the way Signal does it). This would allow people to check whether an unknown public key has been inserted in the conversation. Basic usage wouldn't be different from the way it is now.
 

BigMcGuire

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I export my entires as PDF files each month...
This is exactly what I do with my Day One. Once the month is over, I'll export everything to a PDF and store it locally and on my Google Drive account.


I too saw the End to End encryption yesterday and was really stoked! Everything went smoothly - love the ability to initiate the encryption on my Mac, then just use a QR code to get the key to my iPad and my iPhone. Everything had to be re-downloaded but it didn't take more than 5 mins (1200 entries and 1300+ photos). A+! One of the few apps that I REALLY enjoy and rely on and use on an almost daily basis. I'm just happy they didn't decide to charge for this upgrade like most companies seem to be doing today and I hope they're doing well financially as to continue working on Day One for years and years to come (I'd gladly pay some $ to offset my data usage on their servers).

This app is great. Love the ability to look where I've been and see entries years ago on this day.


Anyone else notice the screen where you encrypt your journal --- it says: Not available on Android or Web App? (Are these coming soon?)
 
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jarred125

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There is really no contradiction. The only thing missing in iMessage to provide full security is a way to verify the identity of the peers when needed, e.g. using a fingerprint of their public keys (similar to the way Signal does it). This would allow people to check whether an unknown public key has been inserted in the conversation. Basic usage wouldn't be different from the way it is now.
Who manages the private key in that case?
 

Rigby

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Who manages the private key in that case?
The private keys are generated on the users' devices and are never sent to Apple (that's how it works today). The potential risk in iMessage is just that Apple could in theory surrepititiously insert their own public keys into a conversation and use the corresponding private keys to decrypt the messages.
 
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jarred125

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The private keys are generated on the users' devices and are never sent to Apple (that's how it works today). The potential risk in iMessage is just that Apple could in theory surrepititiously insert their own public keys into a conversation and use the corresponding private keys to decrypt the messages.
Thanks for making that clearer. I had a slight understanding of it or so I thought. Too easy to get things backwards in my little pea brain :D.
 

miknos

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There is always a trade-off, either its easier to use (iMessage) or hard because you have to manage the key exchange. For this app it's a no-brainer, but for iMessage would you really want to have to exchange encryption keys with each person you wanted to communicate with? That kind of security is likely not required on a day to day basis for the vast majority of us and I prefer the easier to use methods for that, but there are some nice options for when you really need to ensure security but again, it's not "easy".
E2EE doesn't have to be difficult to use. Whatsapp, Signal, iMessage, Protonmail, etc are all E2EE.

It's just like every service you use. The important part is to never forget your password.
 

GrumpyMom

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Sep 11, 2014
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I export my entires as PDF files each month, then use an app to hide it, I use Hider 2 for that.

The PDF files exported by DayOne looks gorgeous and frankly, I think they look even better than viewing my journal in the app interface!

Also, you can order prints of your data but I'm not quite familiar with that.
Thank you! Well this app sounds like a good possibility for me.
 
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AppleInLVX

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Anyone else notice the screen where you encrypt your journal --- it says: Not available on Android or Web App? (Are these coming soon?)
Web app is already live for viewing (can't edit or create yet though) https://app.dayone.me/login

As for saving things, I've taken to making annual PDF backups of my journals. I have been using Day One to make an entry with a photo every single day for nearly 5 years. It's amazing software. I never thought I'd keep journaling up as a habit, but this app really lit the fire in me for whatever reason. It's now part of my morning routine to see what happened on this day in years gone by--the process gets more rich with each passing year.

But yeah, one PDF per year, stored securely on sync. I printed off the first year's worth of entries but it was pretty ugly and *huge*. Sadly their new publish option isn't yet available in Canada, and there's no time line, but depending upon how well it renders the document, I may do that going forward.

I also do a plain text export, just for the sake of backward compatibility, but that only preserves the text.
 
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triton100

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Web app is already live for viewing (can't edit or create yet though) https://app.dayone.me/login

As for saving things, I've taken to making annual PDF backups of my journals. I have been using Day One to make an entry with a photo every single day for nearly 5 years. It's amazing software. I never thought I'd keep journaling up as a habit, but this app really lit the fire in me for whatever reason. It's now part of my morning routine to see what happened on this day in years gone by--the process gets more rich with each passing year.

But yeah, one PDF per year, stored securely on sync. I printed off the first year's worth of entries but it was pretty ugly and *huge*. Sadly their new publish option isn't yet available in Canada, and there's no time line, but depending upon how well it renders the document, I may do that going forward.

I also do a plain text export, just for the sake of backward compatibility, but that only preserves the text.
Out of interest what benefit do you find in looking back at what you were doing a year ok this day
 

AppleInLVX

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Out of interest what benefit do you find in looking back at what you were doing a year ok this day
There's a couple things I'd consider benefits. I can see where I was a year or more ago with regard to what I was doing and see if I've moved the needle in any way, see which of my great ideas were just ideas and which had legs. I'm a hobby gardener, and so I can see when the plants are out this year vs. previous years and thereby track how the seasons are going. More surprizingly, I've noticed patterns in the wheel of the year that keep repeating year over year and it's just plain neat to see how precise the seasons are. A particular flower or bud will appear on *exactly* the same day. Sometimes I'll find I do yearly tasks like road trips on exactly the same days without thinking or planning, things I think are spontaneous are in fact running on feelings that get triggered by the time of year. It's hard to explain, but very cool. Also, the photos I take show the evolution of the world around me and document what I've been up to, how I've felt, etc. I've found it to be a really nifty sort of exercise. Whether these things are "benefits" are probably down to what you value personally, but it's been good for me.
 

triton100

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Dec 15, 2010
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There's a couple things I'd consider benefits. I can see where I was a year or more ago with regard to what I was doing and see if I've moved the needle in any way, see which of my great ideas were just ideas and which had legs. I'm a hobby gardener, and so I can see when the plants are out this year vs. previous years and thereby track how the seasons are going. More surprizingly, I've noticed patterns in the wheel of the year that keep repeating year over year and it's just plain neat to see how precise the seasons are. A particular flower or bud will appear on *exactly* the same day. Sometimes I'll find I do yearly tasks like road trips on exactly the same days without thinking or planning, things I think are spontaneous are in fact running on feelings that get triggered by the time of year. It's hard to explain, but very cool. Also, the photos I take show the evolution of the world around me and document what I've been up to, how I've felt, etc. I've found it to be a really nifty sort of exercise. Whether these things are "benefits" are probably down to what you value personally, but it's been good for me.
That's very interesting. I never use that function on the app. Maybe I should
 
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BigMcGuire

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There's a couple things I'd consider benefits. I can see where I was a year or more ago with regard to what I was doing and see if I've moved the needle in any way, see which of my great ideas were just ideas and which had legs. I'm a hobby gardener, and so I can see when the plants are out this year vs. previous years and thereby track how the seasons are going. More surprizingly, I've noticed patterns in the wheel of the year that keep repeating year over year and it's just plain neat to see how precise the seasons are. A particular flower or bud will appear on *exactly* the same day. Sometimes I'll find I do yearly tasks like road trips on exactly the same days without thinking or planning, things I think are spontaneous are in fact running on feelings that get triggered by the time of year. It's hard to explain, but very cool. Also, the photos I take show the evolution of the world around me and document what I've been up to, how I've felt, etc. I've found it to be a really nifty sort of exercise. Whether these things are "benefits" are probably down to what you value personally, but it's been good for me.
What an awesome write up! Really great!

I was shocked to see that for my "goals" part of my daily logs - I was saying almost the IDENTICAL stuff years ago. Like wait a minute, I've been trying to do this for 2 years now? Really? lol. What am I not doing to make this happen? It was incredibly shocking.

I take a lot of photos of my surroundings just so I can remember what I did during the day - to make it easier to write a "daily log" when I get back home. This helps me with the self improvement process - noticing small things, habits, etc...

The biggest benefit that I've found writing these logs is the act of de-stressing. The world, my job, etc... is incredibly stressful. It's an incredibly de-stressing exercise to write my thoughts down, talk about my day, and recording information.

Many many years ago, while watching Star Trek episodes, I thought how cool it was - the Captain's log - daily logs of the crew. That's what started my whole "daily log" routine.

I've found that the quality of my "logs" go up if I don't do one every day because it's not every day I feel like spending 10-15 mins writing about my day. When I was writing every day it became a monotonous chore where I was listing off the things I did. When I write once or twice a week, I remember more, talk about thoughts, state of mind, etc...

I figure for the cost of 30 mins a few times a week - the relaxing (anti-stress) action is incredibly beneficial.
 
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AppleInLVX

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What an awesome write up! Really great!

I was shocked to see that for my "goals" part of my daily logs - I was saying almost the IDENTICAL stuff years ago. Like wait a minute, I've been trying to do this for 2 years now? Really? lol. What am I not doing to make this happen? It was incredibly shocking.

I take a lot of photos of my surroundings just so I can remember what I did during the day - to make it easier to write a "daily log" when I get back home. This helps me with the self improvement process - noticing small things, habits, etc...

The biggest benefit that I've found writing these logs is the act of de-stressing. The world, my job, etc... is incredibly stressful. It's an incredibly de-stressing exercise to write my thoughts down, talk about my day, and recording information.

Many many years ago, while watching Star Trek episodes, I thought how cool it was - the Captain's log - daily logs of the crew. That's what started my whole "daily log" routine.

I've found that the quality of my "logs" go up if I don't do one every day because it's not every day I feel like spending 10-15 mins writing about my day. When I was writing every day it became a monotonous chore where I was listing off the things I did. When I write once or twice a week, I remember more, talk about thoughts, state of mind, etc...

I figure for the cost of 30 mins a few times a week - the relaxing (anti-stress) action is incredibly beneficial.
I'm totally the same way with the goals. If I read something that's still going on two years after I first wrote about it, it's almost certainly time to let it go. As for the rest, I agree. I find that my few sentences a day pay off as I go through life and take some time over breakfast to look back. That, and i totally wonder what a future social sciences person might get out of such a record. :)

In any case, yeah.. Day One. Go get it. :p (not affiliated in any way)
 
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nobodykeys

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Aug 18, 2009
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Everything went smoothly - love the ability to initiate the encryption on my Mac, then just use a QR code to get the key to my iPad and my iPhone. Everything had to be re-downloaded but it didn't take more than 5 mins (1200 entries and 1300+ photos).
Thanks for sharing this. Just a check on the UX - is the QR code key share just a 1 time thing? Do new end-to-end encrypted entries now just automatically sync across all your devices?
 

BigMcGuire

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Thanks for sharing this. Just a check on the UX - is the QR code key share just a 1 time thing? Do new end-to-end encrypted entries now just automatically sync across all your devices?
A one time thing. So I had to type in the code for my Mac mini but my iPad Air 2 and iPhone I was able to scan the qr code. Just once per device. And yep I create a new entry and it syncs to all devices. It is a new journal that is encrypted.
 

jb-net

macrumors member
Apr 7, 2012
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Austria
Great news, I really like the app but stayed away from sync due to security concerns. Now that they support E2E Encryption I might take another look.

Hopefully the will add an option to create a custom key - the only way to be secure that it really is a random key.