Decrypting an OpenSSL PEM Encoded RSA private key with Java?

You need to use a non-standard, OpenSSL method for deriving the decryption key. Then use that to decrypt the PKCS-#1–encoded key—what you are working with is not a PKCS #8 envelope. You'll also need the IV from the header as input to these processes.

It looks something like this:

  static RSAPrivateKey decrypt(String keyDataStr, String ivHex, String password)
    throws GeneralSecurityException
  {
    byte[] pw = password.getBytes(StandardCharsets.UTF_8);
    byte[] iv = h2b(ivHex);
    SecretKey secret = opensslKDF(pw, iv);
    Cipher cipher = Cipher.getInstance("DESede/CBC/PKCS5Padding");
    cipher.init(Cipher.DECRYPT_MODE, secret, new IvParameterSpec(iv));
    byte[] pkcs1 = cipher.doFinal(Base64.getMimeDecoder().decode(keyDataStr));
    /* See note for definition of "decodeRSAPrivatePKCS1" */
    RSAPrivateCrtKeySpec spec = decodeRSAPrivatePKCS1(pkcs1);
    KeyFactory rsa = KeyFactory.getInstance("RSA");
    return (RSAPrivateKey) rsa.generatePrivate(spec);
  }

  private static SecretKey opensslKDF(byte[] pw, byte[] iv)
    throws NoSuchAlgorithmException
  {
    MessageDigest md5 = MessageDigest.getInstance("MD5");
    md5.update(pw);
    md5.update(iv);
    byte[] d0 = md5.digest();
    md5.update(d0);
    md5.update(pw);
    md5.update(iv);
    byte[] d1 = md5.digest();
    byte[] key = new byte[24];
    System.arraycopy(d0, 0, key, 0, 16);
    System.arraycopy(d1, 0, key, 16, 8);
    return new SecretKeySpec(key, "DESede");
  }

  private static byte[] h2b(CharSequence s)
  {
    int len = s.length();
    byte[] b = new byte[len / 2];
    for (int src = 0, dst = 0; src < len; ++dst) {
      int hi = Character.digit(s.charAt(src++), 16);
      int lo = Character.digit(s.charAt(src++), 16);
      b[dst] = (byte) (hi << 4 | lo);
    }
    return b;
  }

This is already a lot of code, so I will link to another answer for the definition of the decodeRSAPrivatePKCS1() method.


Java code example below shows how to construct the decryption key to obtain the underlying RSA key from an encrypted private key created using the openssl 1.0.x genrsa command; specifically from the following genrsa options that may have been leveraged:

-des encrypt the generated key with DES in cbc mode

-des3 encrypt the generated key with DES in ede cbc mode (168 bit key)

-aes128, -aes192, -aes256 encrypt PEM output with cbc aes

Above options result in encrypted RSA private key of the form ...

-----BEGIN RSA PRIVATE KEY-----
Proc-Type: 4,ENCRYPTED
DEK-Info: AAA,BBB
...

Where AAA would be one of:

DES-CBC, DES-EDE3-CBC, AES-128-CBC, AES-192-CBC, AES-256-CBC

AND BBB is the hex-encoded IV value

KeyFactory factory = KeyFactory.getInstance("RSA");
KeySpec keySpec = null;
RSAPrivateKey privateKey = null;

Matcher matcher = OPENSSL_ENCRYPTED_RSA_PRIVATEKEY_PATTERN.matcher(pemContents);
if (matcher.matches())
{
    String encryptionDetails = matcher.group(1).trim(); // e.g. AES-256-CBC,XXXXXXX
    String encryptedKey = matcher.group(2).replaceAll("\\s", ""); // remove tabs / spaces / newlines / carriage return etc

    System.out.println("PEM appears to be OpenSSL Encrypted RSA Private Key; Encryption details : "
        + encryptionDetails + "; Key : " + encryptedKey);

    byte[] encryptedBinaryKey = java.util.Base64.getDecoder().decode(encryptedKey);

    String[] encryptionDetailsParts = encryptionDetails.split(",");
    if (encryptionDetailsParts.length == 2)
    {
        String encryptionAlgorithm = encryptionDetailsParts[0];
        String encryptedAlgorithmParams = encryptionDetailsParts[1]; // i.e. the initialization vector in hex

        byte[] pw = new String(password).getBytes(StandardCharsets.UTF_8);
        byte[] iv = fromHex(encryptedAlgorithmParams);

        MessageDigest digest = MessageDigest.getInstance("MD5");

        // we need to come up with the encryption key
        
        // first round digest based on password and first 8-bytes of IV ..
        digest.update(pw);
        digest.update(iv, 0, 8);

        byte[] round1Digest = digest.digest(); // The digest is reset after this call is made.
        
        // second round digest based on first round digest, password, and first 8-bytes of IV ...
        digest.update(round1Digest);
        digest.update(pw);
        digest.update(iv, 0, 8);

        byte[] round2Digest = digest.digest();

        Cipher cipher = null;
        SecretKey secretKey = null;
        byte[] key = null;
        byte[] pkcs1 = null;

        if ("AES-256-CBC".equals(encryptionAlgorithm))
        {
            cipher = Cipher.getInstance("AES/CBC/PKCS5Padding");

            key = new byte[32]; // 256 bit key  (block size still 128-bit)
            System.arraycopy(round1Digest, 0, key, 0, 16);
            System.arraycopy(round2Digest, 0, key, 16, 16);

            secretKey = new SecretKeySpec(key, "AES");
        }
        else if ("AES-192-CBC".equals(encryptionAlgorithm))
        {
            cipher = Cipher.getInstance("AES/CBC/PKCS5Padding");

            key = new byte[24]; // key size of 24 bytes
            System.arraycopy(round1Digest, 0, key, 0, 16);
            System.arraycopy(round2Digest, 0, key, 16, 8);

            secretKey = new SecretKeySpec(key, "AES");
        }
        else if ("AES-128-CBC".equals(encryptionAlgorithm))
        {
            cipher = Cipher.getInstance("AES/CBC/PKCS5Padding");

            key = new byte[16]; // 128 bit key
            System.arraycopy(round1Digest, 0, key, 0, 16);

            secretKey = new SecretKeySpec(key, "AES");
        }
        else if ("DES-EDE3-CBC".equals(encryptionAlgorithm))
        {
            cipher = Cipher.getInstance("DESede/CBC/PKCS5Padding");
            
            key = new byte[24]; // key size of 24 bytes
            System.arraycopy(round1Digest, 0, key, 0, 16);
            System.arraycopy(round2Digest, 0, key, 16, 8);

            secretKey = new SecretKeySpec(key, "DESede");
        }
        else if ("DES-CBC".equals(encryptionAlgorithm))
        {
            cipher = Cipher.getInstance("DES/CBC/PKCS5Padding");
            
            key = new byte[8]; // key size of 8 bytes
            System.arraycopy(round1Digest, 0, key, 0, 8);

            secretKey = new SecretKeySpec(key, "DES");
        }

        cipher.init(Cipher.DECRYPT_MODE, secretKey, new IvParameterSpec(iv));

        pkcs1 = cipher.doFinal(encryptedBinaryKey);

        keySpec = pkcs1ParsePrivateKey(pkcs1);

        privateKey = (RSAPrivateKey) factory.generatePrivate(keySpec);
    }
}

The regular expression ...

static final String OPENSSL_ENCRYPTED_RSA_PRIVATEKEY_REGEX = "\\s*" 
+ "-----BEGIN RSA PUBLIC KEY-----" + "\\s*"
+ "Proc-Type: 4,ENCRYPTED" + "\\s*"
+ "DEK-Info:" + "\\s*([^\\s]+)" + "\\s+"
+ "([\\s\\S]*)"
+ "-----END RSA PUBLIC KEY-----" + "\\s*";

static final Pattern OPENSSL_ENCRYPTED_RSA_PRIVATEKEY_PATTERN = Pattern.compile(OPENSSL_ENCRYPTED_RSA_PRIVATEKEY_REGEX);

the fromHex(...) method ...

public static byte[] fromHex(String hexString)
{
    byte[] bytes = new byte[hexString.length() / 2];
    for (int i = 0; i < hexString.length(); i += 2)
    {
        bytes[i / 2] = (byte) ((Character.digit(hexString.charAt(i), 16) << 4)
            + Character.digit(hexString.charAt(i + 1), 16));
    }
    return bytes;
}