I am building a web app which will use the DropBox API to save data to a users folder. There are 2 parts to the site: an ASP.NET MVC Front End and a Windows Service. At the moment, I was planning on dumping the oauth string and user Id from the authorisation request to database, and use that in both the service and website calls, but how should I store that information? Should I encrypt it or not? And if so, any recommendations on how? For example, if the database is encrypted, how do I store the Encryption key?
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Do you want to always have access to the user’s drop box account or only when they are loged in to your system ? I assume the former since you want to store the o-auth token. In that case see the encryption discussion below for why you can’t really encrypt it. I’d suggest however, that you take the safer route and only access drop box either when the user is loged in or shortly their after (i.e. don’t store persistent auth tokens )
The secure approach
When the user logs in, get an oauth token from the dropbox, use it to perform whatever actions they want and if necessary keep it around after the log out to keep doing tasks ( background sync or something). However, once that last task finishes, delete the token. This means that if your server is compromised only the loged in users or those that recently loged out are exposed. Its a mitigation, but its the best you can get.
I believe you can do this with o-auth without explicitly prompting the user for a new token every time. If not, I know you can do it with opendID, though I could see drop box not allowing that.
Finally, if neither of those works, you could store the o-auth key persistently encrypted under a key derived from the users password with say PBKDF2(with like 5000 iterations). When they log in, you decrypt it, use it, and then delete the cleartext copy. The downside to this is 1) password resets require a fresh o-auth token since you no longer have their key and 2) the user must log into your site itself and give you a password so you can derive the key. They cannot use openid.
Encryption
If you want continual access to the oauth tokem you can’t really do meaningful encryption. As you said, where would you store the key ? For a web service, there is no good answer. For an end user system, the answer is derive the key from the user’s password which you the must not store(this is what lastpass does). You can’t do this because you want to have access to the data even when the end (wepapp) users are not loged in.
Ok, what about the sysadmin’s password? Well since the server is running all the time, this is worthless since a compromise would still reveal the keys. Worse, reboots would take down your app because it needs the sys admin’s password to decrypt its data and they are not likely their when the system crashes at 3am.
They make Hardware Security Modules that store keys and perform crypto operations with them, so an attacker could get the key because it never leaves the HSM. However, an attacker could just ask the TPM to decrypt the o-auth string. The best you could do was rate limit this so an attack could only get like 1000 tokens an hour (obviously that rate needs to be larger that legit usage). Given that HSMs are expensive and make hosting expensive because you need a dedicated system, this is not worth it.
In an ideal world, you’d use a TPM to hold the keys and have it only release the data if the system is not compromised. Unfortunately, TPM’s currently only support verifying that the correct program (e.g. the boot-loader,then kernel, then user land program) was loaded. They do nothing if that program is compromised after it is loaded, which is the threat vector here. This might change in the next 5 to 10 years, but that does not help you now.