OpenSSL AES CBC 256 in .NET for interop with Ruby

cypher.rb

require 'rubygems'
require 'bundler'
require 'gibberish'

password = '181cc0b200124dc748c96d8fdefe2cb3f21b48212898c2e3dd705a4c8415a5abb15b3c43ccb9e9db27e6c9ad1df1b927377c8dd6bb3d07746bc3cec7c67ca016'
cipher = Gibberish::AES.new(password)

cypher_text = cipher.encrypt("Hello from Ruby!")
plain_text = cipher.decrypt('U2FsdGVkX18GXWJnusOQi55IhmvfdVyjTLjAmmtcAmg=')

print "Encrypted string is: "
p cypher_text
puts "Decrypted string is: '#{plain_text}'"

OpenSslAes.cs

using System;
using System.Collections.Generic;
using System.IO;
using System.Security.Cryptography;
using System.Text;

namespace dotnet_aes
{
    public class OpenSslAes
    {
        public static string Encrypt(string plainText, string passphrase)
        {
            byte[] key, iv;
            var salt = new byte[8];
            new RNGCryptoServiceProvider().GetNonZeroBytes(salt);

            EvpBytesToKey(passphrase, salt, out key, out iv);

            byte[] encryptedBytes = AesEncrypt(plainText, key, iv);
            var encryptedBytesWithSalt = CombineSaltAndEncryptedData(encryptedBytes, salt);
            return Convert.ToBase64String(encryptedBytesWithSalt);
        }

        // OpenSSL prefixes the combined encrypted data and salt with "Salted__"
        private static byte[] CombineSaltAndEncryptedData(byte[] encryptedData, byte[] salt)
        {
            var encryptedBytesWithSalt = new byte[salt.Length + encryptedData.Length + 8];
            Buffer.BlockCopy(Encoding.ASCII.GetBytes("Salted__"), 0, encryptedBytesWithSalt, 0, 8);
            Buffer.BlockCopy(salt, 0, encryptedBytesWithSalt, 8, salt.Length);
            Buffer.BlockCopy(encryptedData, 0, encryptedBytesWithSalt, salt.Length + 8, encryptedData.Length);
            return encryptedBytesWithSalt;
        }

        public static string Decrypt(string encrypted, string passphrase)
        {
            byte[] encryptedBytesWithSalt = Convert.FromBase64String(encrypted);

            var salt = ExtractSalt(encryptedBytesWithSalt);
            var encryptedBytes = ExtractEncryptedData(salt, encryptedBytesWithSalt);

            byte[] key, iv;
            EvpBytesToKey(passphrase, salt, out key, out iv);
            return AesDecrypt(encryptedBytes, key, iv);
        }


        // Pull the data out from the combined salt and data
        private static byte[] ExtractEncryptedData(byte[] salt, byte[] encryptedBytesWithSalt)
        {
            var encryptedBytes = new byte[encryptedBytesWithSalt.Length - salt.Length - 8];
            Buffer.BlockCopy(encryptedBytesWithSalt, salt.Length + 8, encryptedBytes, 0, encryptedBytes.Length);
            return encryptedBytes;
        }

        // The salt is located in the first 8 bytes of the combined encrypted data and salt bytes
        private static byte[] ExtractSalt(byte[] encryptedBytesWithSalt)
        {
            var salt = new byte[8];
            Buffer.BlockCopy(encryptedBytesWithSalt, 8, salt, 0, salt.Length);
            return salt;
        }

        // Key derivation algorithm used by OpenSSL
        //
        // Derives a key and IV from the passphrase and salt using a hash algorithm (in this case, MD5).
        //
        // Refer to http://www.openssl.org/docs/crypto/EVP_BytesToKey.html#KEY_DERIVATION_ALGORITHM
        private static void EvpBytesToKey(string passphrase, byte[] salt, out byte[] key, out byte[] iv)
        {
            var concatenatedHashes = new List<byte>(48);

            byte[] password = Encoding.UTF8.GetBytes(passphrase);
            byte[] currentHash = new byte[0];
            MD5 md5 = MD5.Create();
            bool enoughBytesForKey = false;

            while (!enoughBytesForKey)
            {
                int preHashLength = currentHash.Length + password.Length + salt.Length;
                byte[] preHash = new byte[preHashLength];

                Buffer.BlockCopy(currentHash, 0, preHash, 0, currentHash.Length);
                Buffer.BlockCopy(password, 0, preHash, currentHash.Length, password.Length);
                Buffer.BlockCopy(salt, 0, preHash, currentHash.Length + password.Length, salt.Length);

                currentHash = md5.ComputeHash(preHash);
                concatenatedHashes.AddRange(currentHash);

                if (concatenatedHashes.Count >= 48) enoughBytesForKey = true;
            }

            key = new byte[32];
            iv = new byte[16];
            concatenatedHashes.CopyTo(0, key, 0, 32);
            concatenatedHashes.CopyTo(32, iv, 0, 16);

            md5.Clear();
            md5 = null;
        }

        static byte[] AesEncrypt(string plainText, byte[] key, byte[] iv)
        {
            MemoryStream memoryStream;
            RijndaelManaged aesAlgorithm = null;

            try
            {
                aesAlgorithm = new RijndaelManaged
                                   {
                                       Mode = CipherMode.CBC,
                                       KeySize = 256,
                                       BlockSize = 128,
                                       Key = key,
                                       IV = iv
                                   };

                var cryptoTransform = aesAlgorithm.CreateEncryptor(aesAlgorithm.Key, aesAlgorithm.IV);
                memoryStream = new MemoryStream();

                using (var cryptoStream = new CryptoStream(memoryStream, cryptoTransform, CryptoStreamMode.Write))
                {
                    using (var streamWriter = new StreamWriter(cryptoStream))
                    {
                        streamWriter.Write(plainText);
                        streamWriter.Flush();
                        streamWriter.Close();
                    }
                }
            }
            finally
            {
                if (aesAlgorithm != null) aesAlgorithm.Clear();
            }

            return memoryStream.ToArray();
        }

        static string AesDecrypt(byte[] cipherText, byte[] key, byte[] iv)
        {
            RijndaelManaged aesAlgorithm = null;
            string plaintext;

            try
            {
                aesAlgorithm = new RijndaelManaged
                                   {
                                       Mode = CipherMode.CBC,
                                       KeySize = 256,
                                       BlockSize = 128,
                                       Key = key,
                                       IV = iv
                                   };

                ICryptoTransform decryptor = aesAlgorithm.CreateDecryptor(aesAlgorithm.Key, aesAlgorithm.IV);

                using (var memoryStream = new MemoryStream(cipherText))
                {
                    using (var cryptoStream = new CryptoStream(memoryStream, decryptor, CryptoStreamMode.Read))
                    {
                        using (var streamReader = new StreamReader(cryptoStream))
                        {
                            plaintext = streamReader.ReadToEnd();
                            streamReader.Close();
                        }
                    }
                }
            }
            finally
            {
                if (aesAlgorithm != null) aesAlgorithm.Clear();
            }

            return plaintext;
        }
    }
}

program.cs

using System;

namespace dotnet_aes
{
    class Program
    {
        private const string DotNetPlainText = "Hello from .NET";
        private const string CipherBase64 = "U2FsdGVkX1+wqU8tchOuA2G2I5ceNzad86pb7p2371vKJulvMCuBPQTKo5vG\ncEF9\n";
        private const string Password = "181cc0b200124dc748c96d8fdefe2cb3f21b48212898c2e3dd705a4c8415a5abb15b3c43ccb9e9db27e6c9ad1df1b927377c8dd6bb3d07746bc3cec7c67ca016";

        static void Main()
        {
            DemoDecryption();
            DemoEncryption();
            Console.ReadLine();
        }

        private static void DemoDecryption()
        {
            var plainText = OpenSslAes.Decrypt(CipherBase64, Password);
            Console.WriteLine("Decrypted string is: '{0}'", plainText);
        }

        private static void DemoEncryption()
        {
            var plainText = OpenSslAes.Encrypt(DotNetPlainText, Password);
            Console.WriteLine("Encrypted string is: '{0}'", plainText);
        }
    }
}

@onyxraven Hi there.

I'm sorry that I've only just seen your message after all this time. You don't need to attribute me... this is public, after all. I don't remember the details concerning the writing of this, but I suspect that I patched it together from various snippets of code lying about the web, anyway!

Hi Scott, exactly what I was looking. Works on the ruby and .net sides. However, if I change the password it encrypts OK but on the .Net side I get an exception (same password of course)
password = '7B932AFA6AA07F75D2F3F6997C5809ECBB845FCD619265D52AE6F3FA29911C1E834AFAC5E06D3AA568FE8D9321CBB27FB9916620EC9B5756A20C97DE1DB2B5D7'

Private Const as String = "7B932AFA6AA07F75D2F3F6997C5809ECBB845FCD619265D52AE6F3FA29911C1E834AFAC5E06D3AA568FE8D9321CBB27FB9916620EC9B5756A20C97DE1DB2B5D7"

Any ideas ??