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I'm currently working on a class that encrypts large amounts of text with a randomly generated encryption key encrypted by a X509 certificate from a smart card, using a RSACryptoServiceProvider to perform the master key encryption and decryption operations. However, when I have the fOEAP padding option set to true, I have the "Error while decoding OAEP padding" error on decryption every time. I've checked the key size and it is within acceptable limits. And I've gone through breakpoints to make sure that the Base64 string that gets returned from the encryption function is the exact same as the encrypted Base64 string that gets passed back to the decryption function when the file gets loaded again.

The key pair is definitely correct, since it works fine without OAEP. And I've checked the text encoding too.

EDIT: It turns out this could be a smart card specific issue, when I tried decryption with a local X509 certificate the decryption succeeded.

EDIT: This is the decryption code that fails:

string TestString = "Hello World!";
X509Certificate2 cert = DRXEncrypter.GetCertificate("Select a test certificate", "Select a certificate to use for this test from the local store.");
string key = DRXEncrypter.GenerateEncryptionKey(214);
Console.WriteLine("Encryption Key: " + key);

string encrypted = DRXEncrypter.EncryptBody(TestString, key);
Console.WriteLine("Encrypted Body: " + encrypted);

string cryptokey = DRXEncrypter.EncryptWithCert(cert, key);
Console.WriteLine("Encrypted Decryption Key: " + cryptokey);

string decrypted = DRXEncrypter.DecryptBody(encrypted, cryptokey, cert);
Console.WriteLine("Decrypted Body: " + decrypted);

Console.WriteLine("Output String: " + decrypted + ".");

Here is the code from the crypto provider class I've written. I've been stuck on this issue for hours, so it would be great if someone could help me out.

using System;
using System.Collections.Generic;
using System.Linq;
using System.Text;
using System.Threading.Tasks;
using System.Security.Cryptography;
using System.Security.Cryptography.X509Certificates;
using System.IO;

namespace CoreDRXEditor
{
public class DRXEncrypter
{
    private byte[] Salt = Encoding.ASCII.GetBytes("81PO9j8I1a94j");
    private string EncryptionKey;
    private const bool UseOAEP = true;

    public DRXEncrypter(string EncryptionKey)
    {
        this.EncryptionKey = EncryptionKey;
    }

    public static string EncryptBody(string body, string encryptionkey)
    {
        // Use the plaintext master key to encrypt the body.
        DRXEncrypter enc = new DRXEncrypter(encryptionkey);

        // Encrypt the body.
        return enc.Encrypt(body);
    }

    public static int GetMaxKeySize(X509Certificate2 cert)
    {
        RSACryptoServiceProvider csp = cert.PublicKey.Key as RSACryptoServiceProvider;

        return csp.KeySize;
    }

    public static string DecryptBody(string body, string encryptionkey, X509Certificate2 cert)
    {
        // Decrypt the encrypted encryption key with the certificate.
        string DecryptedKey = Convert.ToBase64String(DecryptWithCert(cert, encryptionkey));

        // Create a new DRXEncrypter using the decrypted encryption key to decrypt the body.
        DRXEncrypter enc = new DRXEncrypter(DecryptedKey);

        // Return the decrypted body.
        return enc.Decrypt(body);
    }

    public static string GenerateEncryptionKey(int KeyLength)
    {
        using (RandomNumberGenerator rng = new RNGCryptoServiceProvider())
        {
            byte[] CryptoBytes = new byte[KeyLength];
            rng.GetBytes(CryptoBytes);

            return Convert.ToBase64String(CryptoBytes);
        }
    }

    public static X509Certificate2 GetCertificate(string title, string message)
    {
        X509Store cstore = new X509Store(StoreLocation.CurrentUser);
        cstore.Open(OpenFlags.ReadOnly);

        X509CertificateCollection certs = X509Certificate2UI.SelectFromCollection(cstore.Certificates, title, message, X509SelectionFlag.SingleSelection);

        if (certs.Count == 1)
        {
            X509Certificate2 mcert = certs[0] as X509Certificate2;
            return mcert;
        }
        else
        {
            return null;
        }
    }

    public static string EncryptWithCert(X509Certificate2 cert, string PlainText)
    {
        RSACryptoServiceProvider csp = cert.PublicKey.Key as RSACryptoServiceProvider;

        byte[] PlainBytes = Convert.FromBase64String(PlainText);

        // This converts the plain text into a byte array and then encrypts the raw bytes.
        byte[] CryptoBytes = csp.Encrypt(PlainBytes, UseOAEP);

        // This converts the encrypted bytes into a Base64 string.
        string ReturnString = Convert.ToBase64String(CryptoBytes);

        return ReturnString;
    }

    public static byte[] DecryptWithCert(X509Certificate2 cert, string EncryptedText)
    {
        RSACryptoServiceProvider csp = cert.PrivateKey as RSACryptoServiceProvider;

        //CspParameters csps = new CspParameters();

        byte[] EncryptedBytes = Convert.FromBase64String(EncryptedText);

        // This converts the encrypted, Base64 encoded byte array from EncryptWithCert() to a byte[] and decrypts it.
        byte[] CryptoBytes = csp.Decrypt(EncryptedBytes, UseOAEP);

        return CryptoBytes;
    }

    public string Encrypt(string PlainText)
    {
        RijndaelManaged Algorithm = null;
        string Output = null;

        try
        {
            Rfc2898DeriveBytes PrivateKey = new Rfc2898DeriveBytes(this.EncryptionKey, this.Salt);


            Algorithm = new RijndaelManaged();
            Algorithm.Key = PrivateKey.GetBytes(Algorithm.KeySize / 8);
            Algorithm.Padding = PaddingMode.PKCS7;

            ICryptoTransform Encryption = Algorithm.CreateEncryptor(Algorithm.Key, Algorithm.IV);

            using (MemoryStream msa = new MemoryStream())
            {
                msa.Write(BitConverter.GetBytes(Algorithm.IV.Length), 0, sizeof(int));
                msa.Write(Algorithm.IV, 0, Algorithm.IV.Length);
                using (CryptoStream csa = new CryptoStream(msa, Encryption, CryptoStreamMode.Write))
                {
                    using (StreamWriter swa = new StreamWriter(csa))
                    {
                        swa.Write(PlainText);
                    }
                }
                Output = Convert.ToBase64String(msa.ToArray());
            }
        }
        finally
        {
            if (Algorithm != null)
            {
                Algorithm.Clear();
            }
        }

        return Output;
    }

    public string Decrypt(string EncryptedText)
    {
        RijndaelManaged Algorithm = null;
        string Output = null;

        try
        {
            Rfc2898DeriveBytes PrivateKey = new Rfc2898DeriveBytes(this.EncryptionKey, this.Salt);

            byte[] KeyBytes = Convert.FromBase64String(EncryptedText);
            using (MemoryStream msb = new MemoryStream(KeyBytes))
            {
                Algorithm = new RijndaelManaged();
                Algorithm.Key = PrivateKey.GetBytes(Algorithm.KeySize / 8);
                Algorithm.IV = ReadByteArray(msb);
                Algorithm.Padding = PaddingMode.PKCS7;
                ICryptoTransform Decryption = Algorithm.CreateDecryptor(Algorithm.Key, Algorithm.IV);
                using (CryptoStream csb = new CryptoStream(msb, Decryption, CryptoStreamMode.Read))
                {
                    using (StreamReader srb = new StreamReader(csb))
                    {
                        Output = srb.ReadToEnd();
                    }
                }

            }
        }
        finally
        {
            if (Algorithm != null)
            {
                Algorithm.Clear();
            }
        }

        return Output;
    }

    public static string Sha512(string ToHash)
    {
        using (SHA512 SHA = new SHA512Managed())
        {
            byte[] HashByte = Encoding.UTF8.GetBytes(ToHash);
            byte[] HashBytes = SHA.ComputeHash(HashByte);
            string Hash = System.Text.Encoding.UTF8.GetString(HashBytes, 0, HashBytes.Length);
            return Hash;
        }
    }

    public static string Base64Encode(string data)
    {
        byte[] str = Encoding.UTF8.GetBytes(data);
        return Convert.ToBase64String(str);
    }

    public static string Base64Decode(string data)
    {
        byte[] str = Convert.FromBase64String(data);
        return Encoding.UTF8.GetString(str);
    }

    private byte[] ReadByteArray(Stream st)
    {
        byte[] Length = new byte[sizeof(int)];
        st.Read(Length, 0, Length.Length);
        byte[] Buffer = new byte[BitConverter.ToInt32(Length, 0)];
        st.Read(Buffer, 0, Buffer.Length);

        return Buffer;
    }
}
}
Chris J
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CitadelCore
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  • what encoding is your encryptionkey string? – Dai Bok Jun 09 '17 at 06:56
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    Also see [A bad couple of years for the cryptographic token industry](https://blog.cryptographyengineering.com/2012/06/21/bad-couple-of-years-for-cryptographic/). Are you certain its not PKCS padding? – jww Jun 09 '17 at 12:26
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    Dai Bok: It's base64. See the GenerateEncryptionKey() function. – CitadelCore Jun 09 '17 at 14:10
  • What if you change DecryptWithCert line RSACryptoServiceProvider csp = cert.PrivateKey as RSACryptoServiceProvider to RSACryptoServiceProvider csp = cert.PublicKey.Key as RSACryptoServiceProvider seems that you using different keys to decrypt /encrypt? Does that help – Dai Bok Jun 10 '17 at 23:31
  • As I mentioned, I am using the right keypair. It's just OAEP padding that is the problem. If I wasn't using the right keypair, I wouldn't be able to decrypt it even if I was using PKCS#1. – CitadelCore Jun 11 '17 at 07:50

3 Answers3

0

Make sure your key size is not too small or too large.

See comments from MSDN

The RSACryptoServiceProvider supports key sizes from 384 bits to 16384 bits in increments of 8 bits if you have the Microsoft Enhanced Cryptographic Provider installed. It supports key sizes from 384 bits to 512 bits in increments of 8 bits if you have the Microsoft Base Cryptographic Provider installed.

So you might need to pad short key strings with some bytes to get the minimum key length

Dai Bok
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  • When I try this I get "Unhandled Exception: System.Security.Cryptography.CryptographicException: Bad Length." The smart card's certificate only supports up to 2048-bit encryption. (256 bytes is the max.) – CitadelCore Jun 09 '17 at 14:03
  • Also, the Provider is "Microsoft Enhanced RSA and AES Cryptographic Provider". – CitadelCore Jun 09 '17 at 15:34
0

Ok, I managed to check this and from what I can see, I have problems with some certificates. I am not sure why some certificates work while others don't. It would be good to know why some certificates fail in this case?

Anyway, I created a new self signed certificate using windows "Manage File Encryption Certificates" and used this certificate, and all seems to work.

The out put from your code.

Encryption Key: aUc/GXWDoh2LktaEGeCJfju1dHP118yD/fzfT0iJLuhOq2QeyGpG6m3aBHaxvdH0ufeXRHbMjmlmPgIL/bhABzkT2C5Oa6ZhY3IFXb5t7JXZ3AtUunvtNAnRyFJ7MzklrSZGgQ
vF67DSNfIVE17doKt6j6mkCpSco56ooZCrOs2Mp3vSXqNjvjiwMEfQbk41aYUNVNVNlBGhdNQCIZIAKezQCUpWqzn2II27FIDfqDIEW4ieyzpXC05GzUlGXDxFOiFUPk3n0Y94vgeF8AlCD74eyZtz
WQ==
Encrypted Body: EAAAANS/W7+GGRbT1q5NCYvZlDZYtxaA8g55HzUqP5qxhenn
Encrypted Decryption Key: vc/tcsApmY1503BFi7oSu/RDvZivA1Ed58KJuLoEC6eE8q0BIa6ye2JvtXyxkVbzzL0MA51pZ2ZhMIsfCnBsEDjCgy+JLTZTGM1Mv+em9frFUKb0zHbICnPUa/3H
yd1yOWsdn5ws19QN2dzC6eau+ExhT2T/vyZO4Nf9NdHKnB8n2yB1rrQ/T+N2EYCNH/AVPDAsme6JG7k9Od2XIipBXMyCgXgWYZmQusq+JQjA9d3c4CrQYcg/ERF+K3oZv/gPicBkAR5taxwSxAajGg
bpkJNsbhTMHTN9bOn333qZ6ojlo5e882baZXuZWPr9qtj1b7ONoOyuSx/OvGKjt93BQg==
Decrypted Body: Hello World!
Output String: Hello World!.

Hope that helps

Dai Bok
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  • Yeah, I know that machine certificates work, It's just the certificate on my smart card that fails to work. I've tried with other certificates on the same smart card with different EKUs too. – CitadelCore Jun 10 '17 at 09:46
  • Do you have the private key for that cert? – Dai Bok Jun 10 '17 at 14:07
  • Yes, as I previously mentioned OAEP padding is the only thing that prevents decryption from working. Decryption works fine in PKCS#1 mode. – CitadelCore Jun 10 '17 at 16:08
0

I've been arguing with this today with smartcards (or more accurately, a Yubikey Neo with the smartcard PIV applet enabled); using this code:

var encryptor = (RSACryptoServiceProvider)c.PublicKey.Key;
var decryptor = (RSACryptoServiceProvider)c.PrivateKey;

var encrypt = encryptor.Encrypt(bytes, RSAEncryptionPadding.Pkcs1);
var decrypt = decryptor.Decrypt(encrypt, RSAEncryptionPadding.Pkcs1);

I've found that it matters what padding algo I use. If I use PKCS1 padding, everything works. If I use OaepSHA1, I get the Error while decoding [...] error. If I use anything else (e.g., OaepSHA256) I get a Not supported error.

I can only conclude that my smartcard doesn't properly support OAEP SHA1, but padding with PKCS#1 everything is good.

Even if this answers what you already know, it may be useful as another datapoint for anyone else coming along using smartcards.

Chris J
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