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So if I understand you correctly (Noob here), Alice would need to sign the pair (key.enc, file.enc) to authenticate that those files originated from her.

Without that, Bob could potentially receive any pair of (key,file), which would just decrypt into garbage data.

BTW, variations on that sequence appear all over the internet when searching for "openssl encrypt file with public key"...




This is one of the problems with cryptography: with a little knowledge, you can end up making yourself completely insecure while believing yourself to be very secure.

People generally imagine that "encrypt this block of data" is a simple primitive that does everything you want it to. But naive encryption doesn't work like that. In the worst case, where you use ECB for the block cipher [1], you end up with the ECB penguin: https://blog.filippo.io/the-ecb-penguin/. Your secure crypto becomes a pretty trivial Caesar cipher, just on a larger alphabet. Other modes (such as the CBC mode you used) aren't so bad, but if you have some hint of the structure of the underlying data, you can start perturbing the ciphertext to manipulate the encrypted data.

The modern solution to that problem is "authenticated encryption," which means that you add in an additional guarantee that the ciphertext hasn't been tampered with. Even then, there is still room for doing things incorrectly (padding is a real pain!).

[1] This is so bad it shouldn't ever be an option in any tool.


[1] This is so bad it shouldn't ever be an option in any tool.

And yet it's effectively the default.


No, the problem is that the AES encryption step uses bare AES-CBC. An attacker can flip bits in the ciphertext to make targeted changes to the plaintext. What you want is an authenticated encryption mode, but I don't know that the OpenSSL cli supports any of them.




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