This is a classic FAQ (it is in the very old crypto FAQ), but I will give
a more detailed explanation of the standard answer.

This is impossible!  Once you give any user a password to the file, then
he can secretly share it with other people with the same CD (because
nothing on the CD can be different).  Adding "online checks" and other
such things will not help, because at some point the decryption program
run by the legitimate user must end up with the actual decryption key
for the document and that can then be shared.  Or they can simply
share the decrypted document itself and be done with it.

This is what some people call DRM, and it never does anything good for
anyone except the companies that sell it to document owners.

However if you trust the people you give the decryption key and accept
the risk that there is no technical way to prevent them from sharing the
document without permission (you could still have a contract that will
make it very unpleasant if you catch them), then any regular file
encryption will do.

Good candidates:

PGP/GPG in file encryption mode (not the normal public/private key modes)

openssl enc command line tool with a long random password made using
openssl rand.

No point in doing "double AES" or similar stuff, when stealing the key or
the decrypted document is so much easier than breaking the encryption.

On 11/2/2011 1:27 PM, Joe Flowers wrote:
Hello Everyone,

I would like recommendations and suggestions for encrypting a document on a
distributed CD. I would like someone to be able to open and read the
document only if they have a "password" or secret string or other(?).
I understand there is a limit to how secure this really is, but I would
like it to be reasonably secure for what it is, and that's why I'm asking
the question here.

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?

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.

Thanks!

joe.flow...@nofreewill.com

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