I have just gotten the New IPad - my first foray into the world of Apple. I'm eager to make the most of it that I can, for both personally and for work.

In order for me to be able to use it for work, I really need to find a solution that works seamlessly with DropBox to provide client-side encryption for my files.

Despite searching for hours (days) and downloading and trying all manner of offerings, I just can't find anything that works. The closest I've seen so far is BoxCryptor, but that only works if I manually upload the file via the BoxCryptor client. I want something that will work seamlessly so that Notebooks (or EverNote, etc) think they're using DropBox directly, but the files are being encrypted / decrypted just before they enter or leave DropBox.

Any clues?


4 Answers 4


I use a program called 1Password for secure encryption of files (and other data) and it almost does what you ask.

On my Mac client - it can attach arbitrary files to any entry and securely encrypt them before they get stored into Dropbox, but that isn't the primary purpose of the tool. It has an iOS client that can see files attached in this manner, but not really open them, send them to other programs and it also doesn't let you file things.

So - what you ask is clearly something that could be programmed, but isn't something where there are several well-known solutions and people will just propose several. In fact, there may not be a single solution that uses Dropbox despite how popular and prevalent it has become.

I would suggest you consider Box.net which seeks to be a more enterprise secure version of Dropbox - especially if no-one else has a better suggestion than mine for securing your files before they hit Dropbox.


All your data between your device and the Dropbox storage is encrypted so that no one could sniff your transfers and get your data. Your iPad is most likely the weak link depending on how protected you have it.

There isn't a native way to do it only with Dropbox. To be completely protected, you will have to use some other application to encrypt the file then save it into your Dropbox. That could be BoxCryptor, 1Password, etc.

And along the lines of a more enterprise version of Dropbox, I'd have to recommend Syncplicity. I have the Business Edition and it is great. Allows employees to share files directly without having to email or copy the file to another box. I have management controls to limit what they can do like if they are allowed to save the file off to an SD card (Android devices) in unencrypted format, remote wipe of all the files, etc.

One drawback with Syncplicity is that no third party apps are using it for syncing like with Dropbox and Box.net. Syncplicity is a smaller company but this last year they were acquired by EMC Corporation (a huge world wide storage company) so I hope they push it make Syncplicity more common.

  • Hi, Thanks for that. My main issue is my data is sitting on some third party system completely available for them to access. And unless third party apps support it, there's not much point using it... Jan 2, 2013 at 8:20

The best solution that I found so far is Outline+. It fantastically handles OneNote notebooks.

It allows me to sync automatically via DropBox, which I use for my non-secret notebooks, and (very) manually exchange notebooks direcetly between my PC and iPad via iTunes. As this exchange is direct to my PC and not via a third party I'm comfortable using it for my confidential stuff.

Outline+ Enterprise is in development, and promises client-side encrypted notebooks - that should eliminate the current manual copying via iTunes.


For MAC OSX machines you can use GPGTools:https://gpgtools.org to encrypt any files using PGP on the client before uploading to DropBox. PGP uses a public key and private key that can be stored in the keychain or entered manually. GPG tools can encyrpt and sign emails, as well as encrypt individual files or folder with up to 4096 bit RSA encryption. You either upload your public key to different public key servers for friends to retrieve your public key. You can also select 2048 bit RSA encryption.

At the current rate of computing power growth or using the worlds fastest supercomputer it will take about 100 years to break 4096 bit PGP encryption. GPGtools has two versions; one for just the Mac OSX email client and a Suite which includes email, file, and folder encryption. I recommend downloading the suite.

iCloud uses 1024 bit RSA encryption so GPGtools 4096 bit encryption is much much stronger and cannot be broken without you revealing your secret key. Choose a long Mnemonic phrase that you CAN EASILY REMEMBER to create the the Public and Private pair of encryption keys i.e "TheReasonILoveNewYorKCityisthegreatnightlifeandbars" If you don't save the phrase to the keychain or forget it you WILL NOT be able to recover or open any of your encrypted files, folders or emails.

GPGTools is open source shareware, it's very simple to use, it has a nice GUI, or you use the built in command line window. Stay safe and use strong encryption for your important documents stored on cloud based services like DropBox.

  • 1
    Can you please add information about how to get GPG running on an iPad to answer the question asked above?
    – nohillside
    Aug 7, 2013 at 7:39
  • 1
    OP is asking about an iPad, not a desktop Mac.
    – Fake Name
    Aug 7, 2013 at 9:25

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