AES-256/CBC encryption with OpenSSL and decryption

Question

I am a newbie to cryptography. My requirement is to decrypt/encrypt the text that is encrypted/decrypted using openssl. The algorithm that we are using is aes-256-cbc in the Openssl. So, I am trying to implement the same functionality in my application. so far after a lot of googling all i was able to do is..

private static string Encryptor(string TextToEncrypt)
{
    //Turn the plaintext into a byte array.
    byte[] PlainTextBytes = System.Text.ASCIIEncoding.ASCII.GetBytes(TextToEncrypt);            

    //Setup the AES providor for our purposes.
    AesCryptoServiceProvider aesProvider = new AesCryptoServiceProvider();

    aesProvider.BlockSize = 128;
    aesProvider.KeySize = 256;  
    //My key and iv that i have used in openssl
    aesProvider.Key = System.Text.Encoding.ASCII.GetBytes(strKey);
    aesProvider.IV = System.Text.Encoding.ASCII.GetBytes(strIV);  
    aesProvider.Padding = PaddingMode.PKCS7;
    aesProvider.Mode = CipherMode.CBC;

    ICryptoTransform cryptoTransform = aesProvider.CreateEncryptor(aesProvider.Key, aesProvider.IV);            
    byte[] EncryptedBytes = cryptoTransform.TransformFinalBlock(PlainTextBytes, 0, PlainTextBytes.Length);
    return Convert.ToBase64String(EncryptedBytes);                        
}

private static string Decryptor(string TextToDecrypt)
{
    byte[] EncryptedBytes = Convert.FromBase64String(TextToDecrypt);

    //Setup the AES provider for decrypting.            
    AesCryptoServiceProvider aesProvider = new AesCryptoServiceProvider();
    //aesProvider.Key = System.Text.Encoding.ASCII.GetBytes(strKey);
    //aesProvider.IV = System.Text.Encoding.ASCII.GetBytes(strIV);
    aesProvider.BlockSize = 128;
    aesProvider.KeySize = 256;  
    //My key and iv that i have used in openssl
    aesProvider.Key = System.Text.Encoding.ASCII.GetBytes(strKey);
    aesProvider.IV = System.Text.Encoding.ASCII.GetBytes(strIV);  
    aesProvider.Padding = PaddingMode.PKCS7;
    aesProvider.Mode = CipherMode.CBC;


    ICryptoTransform cryptoTransform = aesProvider.CreateDecryptor(aesProvider.Key, aesProvider.IV);
    byte[] DecryptedBytes = cryptoTransform.TransformFinalBlock(EncryptedBytes, 0, EncryptedBytes.Length);
    return System.Text.Encoding.ASCII.GetString(DecryptedBytes);
}

My openssl command is

openssl aes-256-cbc -e -nosalt -a -in  inputfile.txt -out  output.txt -k key -iv ivkey

My key length is 32digits and iv is 16digits

Thnx ...

Answer 1

First, read man enc for openssl. -iv is ignored when -k is used. You probably want capital -K. Second, the key and iv values are hexadecimal when used with the openssl tool, if your C# is using the same string as the command line then you need to do appropriate conversions rather than Encoding.ASCII.GetBytes (a 7 bit encoding is never the right answer anyway).

For your plain text, you might as well use Encoding.UTF8.GetBytes/GetString since it is backwards compatible with ASCII.

If for some reason you actually want to use lowercase -k, a password to generate both the key and iv, that is much more difficult as openssl uses it's own key derivation scheme. Also, it is dangerous to use with the -nosalt flag.

-nosalt: doesn't use a salt in the key derivation routines. This option SHOULD NOT be used except for test purposes or compatibility with ancient versions of OpenSSL and SSLeay.

One of the reasons this is dangerous, is due to the fact that IV's should not be predictable or reused for AES-CBC and if you don't use a salt, the passphrase will always produce the same key with the same IV that opens you up to several attacks and can leak info about the plaintext.

You can find out how to derive from passphrase, the same key and IV as openssl from this blog post Decrypting OpenSSL AES files in C# although it is specifically for AES-128 the comments lead you to how to modify for aes-256, from man EVP_BytesToKey:

Hash0 = ''
Hash1 = MD5(Hash0 + Password + Salt)
Hash2 = MD5(Hash1 + Password + Salt)
Hash3 = MD5(Hash2 + Password + Salt)

Key = Hash1 + Hash2
IV = Hash3