How practical would it be to repeatedly encrypt a given file?

Question

I'm currently experimenting with both public-key and personal file encryption. The programs I use have 2048 bit RSA and 256 bit AES level encryption respectively. As a newbie to this stuff (I've only been a cypherpunk for about a month now - and am a little new to information systems) I'm not familiar with RSA algorithms, but that's not relevant here.

I know that unless some secret lab or NSA program happens to have a quantum computer, it is currently impossible to brute force hack the level of security these programs provide, but I was wondering how much more secure it would be to encrypt a file over and over again.

In a nutshell, what I would like to know is this:

1. When I encrypt a file using 256-bit AES, and then encrypt the already encrypted file once more (using 256 again), do I now have the equivalent of 512-bit AES security? This is pretty much a question of whether or not the the number of possible keys a brute force method would potentially have to test would be 2 x 2 to the 256th power or 2 to the 256th power squared. Being pessimistic, I think it is the former but I was wondering if 512-AES really is achievable by simply encrypting with 256-AES twice?
2. Once a file is encrypted several times so that you must keep using different keys or keep putting in passwords at each level of encryption, would someone** even recognize if they have gotten through the first level of encryption? I was thinking that perhaps - if one were to encrypt a file several times requiring several different passwords - a cracker would not have any way of knowing if they have even broken through the first level of encryption since all they would have would still be an encrypted file.

Here's an example:

• Decrypted file
• DKE$jptid UiWe
• oxfialehv u%uk

Pretend for a moment that the last sequence is what a cracker had to work with - to brute-force their way back to the original file, the result they would have to get (prior to cracking through the next level of encryption) would still appear to be a totally useless file (the second line) once they break through the first level of encryption. Does this mean that anyone attempting to use brute-force would have no way of getting back to the original file since they presumably would still see nothing but encrypted files?

These are basically two questions that deal with the same thing: the effect of encrypting the same file over and over again. I have searched the web to find out what effect repeated encryption has on making a file secure, but aside from reading an anecdote somewhere that the answer to the first question is no, I have found nothing that pertains to the second spin on the same topic. I am especially curious about that last question.

**Assuming hypothetically that they somehow brute-forced their way through weak passwords - since this appears to be a technological possibility with 256-AES right now if you know how to make secure ones...

Answer 1

See 3DES

Answer 2

In general, if you encrypt a file with k-bit AES then again with k-bit AES, you only get (k+1) bits of security, rather than 2k bits of security, with a man-in-the-middle attack. The same holds for most types of encryption, like DES. (Note that triple-DES is not simply three rounds of encryption for this reason.)

Further, encrypting a file with method A and then with method B need not be even as strong as encrypting with method B alone! (This would rarely be the case unless method A is seriously flawed, though.) In contrast, you are guaranteed to be at least as strong as method A. (Anyone remembering the name of this theorem is encouraged to leave a comment; I've forgotten.)

Usually you're much better off simply choosing a single method as strong as possible.

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For your second question: Yes, with most methods, an attacker would know that the first layer had been compromised.

Answer 3

More an opinion here...

First, when computer are strong enough to do a brute-force attack on AES-256 for example, it will be also for iterations of the same... doubling or tripling the time or effort is insignificant at that level.

Next, such considerations can be void depending on the application you are trying to use this encryption in... The "secrets" you will need to carry become bigger (number of iterations and all the different keys you will need, if in fact they are different), the time to do the encryption and the decryption will also need to increase.

My hunch is that iterating the encryption does not help much. Either the algorithm is strong enough to sustain a brute-force attach or it is not. The rest is all in the protection of the keys.

More practically, do you think your house is more protected if you have three identical or similar locks on your front door ? (and that includes number of keys for you to carry around, don't loose those keys, make sure windows and back door are secured also...)

Answer 4

Question 1: The size of the solution space is going to be the same for two passes of the 256-bit key as the 512-bit key, since 2^(256+256) = 2^512

The actual running time of each decrypt() may increase non-linearly as the key-size grows (it would depend on the algorithm), in this case I think brute forcing the 256+256 would run faster than the 2^512, but would still be infeasible.

Question 2: There are probably ways to identify certain ciphertext. I wouldn't be surprised if many algorithms leave some signature or artifacts that could be used for identification.