How to store the key used to encrypt files

Question

I'm playing around with an app to backup files to "the cloud" :) and I want to encrypt the files before I store them. That part I have covered, but as this app will be monitoring folders for change and uploading the changed files I need to store the key that I use to encrypt the files with. The idea is that the user provides a password and a key is generated.

At the moment I'm using the .NET Framework to do the encryption. I'm using the RijndaelManaged class to encrypt/decrypt and the PasswordDeriveBytes class to get the key.

But how should I keep the key that is used for encrypting the files? I also want the program start to with Windows and not need to have the user enter their password again.

Answer 1

I'd recommend avoiding using asymmetric encryption for encryption of your files. Asymmetric encryption is significantly more expensive (computationally) than symmetric encryption algorithms of equal strength. For encrypting large files I'd recommend AES over RSA any day.

As to your question - the Data Protection API (DPAPI) Gaurav mentions is your best bet on Windows. How to: Use Data Protection

DPAPI offers ProtectedMemory and ProtectedData. The former allowing you to protect secrets in memory, the latter affords protection for secrets persisted to disk. The API takes care of encryption & decryption for you, and (depending on the specified scope) will protect your data from access/decryption by other users or on other machines.

To use DPAPI in your scenario, I'd recommend taking the users password, generating a symmetric encryption key (e.g. PasswordDeriveBytes), storing that using DPAPI and restricting access to the current user.

Your application can use that key to encrypt all uploads. Your application can obtain the key without re-prompting the user, and the key could be regenerated by the user on a new system.

One downside would be that a malicious application also executed by the same user could potentially obtain the secret key. To protect against this scenario additional entropy (effectively a salt) must be provided in Protect & Unprotect. However implementing this will likely stray from your objective - because now you'll need to prompt the user for something that seems an awful lot like a password.

Also: interesting reading:

You may also find this post from Backblaze an interesting read. Although they do not explain how they support your scenario (encrypted uploads that the cloud provider cannot decipher - only that they offer such a service): http://blog.backblaze.com/2008/11/12/how-to-make-strong-encryption-easy-to-use/

Disclaimer: I am a satisfied Backblaze customer, but am in no other way affiliated with their service.

PS: Do take the time to mark acceptable answers. The community will reward you.

Answer 2

I suggest you to use asymmetric encryption like I described here. That will allow you to only have one single private key to protect (and backup) even while every file will be encrypted with a different symmetric key.

You can also let Windows (actually CryptoAPI) protect the key using a CspParameters (and the right flags) with the RSACryptoServiceProvider. Depending on your flags you can have the key will be available for the logged on user (so it gets as secure as the user login password).

Answer 3

DPAPI was designed to solve this challenge.