> PGP?

Hi

I would look at the openPGP specs.
http://en.m.wikipedia.org/wiki/OpenPGP#OpenPGP

I think you can solve your projects requirements with GnuPG.

If you like to "weld" it better with you software project, you might look at 
Gpgme (http://www.gnupg.org/related_software/gpgme/).
It's basically a c library.

If you like to go a level deeper and also like to avoid GPL (License) you 
should consider implementing a custom file format with OpenSSL.
There you should take a close look at 
http://www.openssl.org/docs/crypto/EVP_SealInit.html#


> 
> Down the same lines, I'm wondering if something like AES-256 should be used 
> with several "rounds" (encrypting the encrypted data N times) to help prevent 
> (slow down) an exhaustive attack?

Better look at GnuPG.
It will encrypt the file with a "session key" AES256.
The key itself it RSA public key encrypted.

> 
> How is something like this usually done? Any suggestions/recommendations 
> inside or outside the box?
> 
> It would also be nice if a common, widely available unencrypting tool could 
> be easily used to unencrypt the document if the secret string is known.

Then you definitively go for openPGP (GnuPG) or S/Mime

In my eyes both format perform bad on large (very large 512MB+).

Jonas

> 
> Thanks!
> 
> joe.flow...@nofreewill.com
> 
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