Create RSA-SHA1 signature

Question

Is it possible to create a RSA-SHA1 signature with a X509-certificate stored in Azure Key Vault? [non-repudiation certificate]

Unfortunately, I can\'t change the has

Answer 1

My blindly shot "professional" opinion is that you are not constructring PKCS#1 DigestInfo structure correctly. Following console application is working fine for me with both SHA1 and SHA256 algorithms (didn't test the others):

using System;
using System.Security.Cryptography;
using System.Security.Cryptography.X509Certificates;
using System.Text;
using System.Threading.Tasks;
using Microsoft.Azure.KeyVault;
using Microsoft.IdentityModel.Clients.ActiveDirectory;

namespace AzureKeyVaultTestApp1
{
    static class Program
    {
        static HashAlgorithmName _hashAlg = HashAlgorithmName.SHA1;
        static string _clientId = "00000000-0000-0000-0000-000000000000";
        static string _clientSecret = "XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX";
        static string _certId = "https://XXXXXXXX.vault.azure.net/certificates/TestCert1/XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX";
        static string _keyId = "https://XXXXXXXX.vault.azure.net/keys/TestCert1/XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX";

        static async Task AuthenticationCallback(string authority, string resource, string scope)
        {
            var context = new AuthenticationContext(authority);
            var result = await context.AcquireTokenAsync(resource, new ClientCredential(_clientId, _clientSecret));
            return result.AccessToken;
        }

        static async Task Main(string[] args)
        {
            KeyVaultClient client = new KeyVaultClient(new KeyVaultClient.AuthenticationCallback(AuthenticationCallback));

            // Compute digest of data
            byte[] dataToSign = Encoding.ASCII.GetBytes("Hello world!");
            byte[] hash = HashAlgorithm.Create(_hashAlg.Name).ComputeHash(dataToSign);

            // Construct DER encoded PKCS#1 DigestInfo structure defined in RFC 8017
            byte[] pkcs1DigestInfo = CreatePkcs1DigestInfo(hash, _hashAlg);

            // Sign digest with private key
            var keyOperationResult = await client.SignAsync(_keyId, "RSNULL", pkcs1DigestInfo).ConfigureAwait(false);
            byte[] signature = keyOperationResult.Result;

            // Get public key from certificate
            var certBundle = await client.GetCertificateAsync(_certId).ConfigureAwait(false);
            X509Certificate2 cert = new X509Certificate2(certBundle.Cer);
            RSA rsaPubKey = cert.GetRSAPublicKey();

            // Verify digest signature with public key
            if (!rsaPubKey.VerifyHash(hash, signature, _hashAlg, RSASignaturePadding.Pkcs1))
                throw new Exception("Invalid signature");
        }

        private static byte[] CreatePkcs1DigestInfo(byte[] hash, HashAlgorithmName hashAlgorithm)
        {
            if (hash == null || hash.Length == 0)
                throw new ArgumentNullException(nameof(hash));

            byte[] pkcs1DigestInfo = null;

            if (hashAlgorithm == HashAlgorithmName.MD5)
            {
                if (hash.Length != 16)
                    throw new ArgumentException("Invalid lenght of hash value");

                pkcs1DigestInfo = new byte[] { 0x30, 0x20, 0x30, 0x0C, 0x06, 0x08, 0x2A, 0x86, 0x48, 0x86, 0xF7, 0x0D, 0x02, 0x05, 0x05, 0x00, 0x04, 0x10, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00 };
                Array.Copy(hash, 0, pkcs1DigestInfo, pkcs1DigestInfo.Length - hash.Length, hash.Length);
            }
            else if (hashAlgorithm == HashAlgorithmName.SHA1)
            {
                if (hash.Length != 20)
                    throw new ArgumentException("Invalid lenght of hash value");

                pkcs1DigestInfo = new byte[] { 0x30, 0x21, 0x30, 0x09, 0x06, 0x05, 0x2B, 0x0E, 0x03, 0x02, 0x1A, 0x05, 0x00, 0x04, 0x14, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00 };
                Array.Copy(hash, 0, pkcs1DigestInfo, pkcs1DigestInfo.Length - hash.Length, hash.Length);
            }
            else if (hashAlgorithm == HashAlgorithmName.SHA256)
            {
                if (hash.Length != 32)
                    throw new ArgumentException("Invalid lenght of hash value");

                pkcs1DigestInfo = new byte[] { 0x30, 0x31, 0x30, 0x0D, 0x06, 0x09, 0x60, 0x86, 0x48, 0x01, 0x65, 0x03, 0x04, 0x02, 0x01, 0x05, 0x00, 0x04, 0x20, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00 };
                Array.Copy(hash, 0, pkcs1DigestInfo, pkcs1DigestInfo.Length - hash.Length, hash.Length);
            }
            else if (hashAlgorithm == HashAlgorithmName.SHA384)
            {
                if (hash.Length != 48)
                    throw new ArgumentException("Invalid lenght of hash value");

                pkcs1DigestInfo = new byte[] { 0x30, 0x41, 0x30, 0x0D, 0x06, 0x09, 0x60, 0x86, 0x48, 0x01, 0x65, 0x03, 0x04, 0x02, 0x02, 0x05, 0x00, 0x04, 0x30, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00 };
                Array.Copy(hash, 0, pkcs1DigestInfo, pkcs1DigestInfo.Length - hash.Length, hash.Length);
            }
            else if (hashAlgorithm == HashAlgorithmName.SHA512)
            {
                if (hash.Length != 64)
                    throw new ArgumentException("Invalid lenght of hash value");

                pkcs1DigestInfo = new byte[] { 0x30, 0x51, 0x30, 0x0D, 0x06, 0x09, 0x60, 0x86, 0x48, 0x01, 0x65, 0x03, 0x04, 0x02, 0x03, 0x05, 0x00, 0x04, 0x40, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00 };
                Array.Copy(hash, 0, pkcs1DigestInfo, pkcs1DigestInfo.Length - hash.Length, hash.Length);
            }

            return pkcs1DigestInfo;
        }
    }
}