SslStream AuthenticateAsClient method getting "The handshake failed due to an unexpected packet format" error

Leon Cao 1 Reputation point
2021-11-26T07:02:39.717+00:00

Our code uses TcpClient and SslStream in C# encounter an error The handshake failed due to an unexpected packet format. when calling AuthenticateAsClient method, the SMTP server is smtp.office365.com, we tried many ways but all not working.

Tried: System.Net.ServicePointManager.SecurityProtocol = SecurityProtocolType.Tls12;

Tried: ssl.AuthenticateAsClient(Server, null, System.Security.Authentication.SslProtocols.Tls12, true);

Tried other AuthenticateAsClient overloading methods all not working.

Also with the tool Microsoft Network Monitor 3.4, we can confirm the Client Hello handshake use the TSL1.2 protocol.

Anyone had encountered a similar issue?

Below is the full code in the console with .NET Framework 8

    class Program
    {
        static void Main(string[] args)
        {
            try
            {
                string Server = "smtp-legacy.office365.com";//raise error
                //This server raise error too
                Server = "smtp.office365.com";//raise same error
                int port = 587;
                //tried this, not working
                //System.Net.ServicePointManager.SecurityProtocol = SecurityProtocolType.Tls12;
                //
                using (var tcp = new System.Net.Sockets.TcpClient())
                {
                    tcp.Connect(Server, port);

                    System.Net.Security.RemoteCertificateValidationCallback remoteCertCallback =
                        new System.Net.Security.RemoteCertificateValidationCallback((Object sender,
                               System.Security.Cryptography.X509Certificates.X509Certificate cert,
                               System.Security.Cryptography.X509Certificates.X509Chain chain,
                               System.Net.Security.SslPolicyErrors Errors) => true);

                    //System.Net.Security.SslStream ssl = 
                    //    new System.Net.Security.SslStream(tcp.GetStream(), false, remoteCertCallback, null);

                    //Try set LocalCertificateSelectionCallback
                    System.Net.Security.SslStream ssl =
                        new System.Net.Security.SslStream(tcp.GetStream(), false, remoteCertCallback, SelectLocalCertificate);

                    //Raise error: The handshake failed due to an unexpected packet format.
                    #region Try to specify the protocol, not working
                    ssl.AuthenticateAsClient(Server, null, System.Security.Authentication.SslProtocols.Tls12, true);
                    #endregion

                    #region Try to set local certificate, not working
                    //tried to set local certificate, not working
                    //X509CertificateCollection clientCertificates = GetLocalCertificates();
                    //ssl.AuthenticateAsClient(Server, clientCertificates, System.Security.Authentication.SslProtocols.Tls12, true);
                    #endregion

                    #region Default way, not working
                    //Raise error: The handshake failed due to an unexpected packet format.
                    //ssl.AuthenticateAsClient(Server);
                    #endregion


                }

            }
            //Raise error: The handshake failed due to an unexpected packet format.
            catch (Exception ex)
            {
                Console.WriteLine(ex.ToString());
            }

            Console.Read();

        }


        public static X509Certificate2Collection GetLocalCertificates()
        {
            X509Certificate2Collection Certificates = null;
            // Read the certificate from the store
            X509Store store = new X509Store(StoreName.My, StoreLocation.LocalMachine);
            try
            {
                store.Open(OpenFlags.ReadOnly);
                //Certificates = store.Certificates.Find(X509FindType.FindBySubjectDistinguishedName,
                //"CN=[YOUR DOMAIN]", false);
                Certificates = store.Certificates;
            }
            finally
            {
                store.Close();
            }

            return Certificates;
        }

        public static X509Certificate SelectLocalCertificate(
            object sender,
            string targetHost,
            X509CertificateCollection localCertificates,
            X509Certificate remoteCertificate,
            string[] acceptableIssuers)
        {
            if (acceptableIssuers != null &&
                acceptableIssuers.Length > 0 &&
                localCertificates != null &&
                localCertificates.Count > 0)
            {
                // Use the first certificate that is from an acceptable issuer.
                foreach (X509Certificate certificate in localCertificates)
                {
                    string issuer = certificate.Issuer;
                    if (Array.IndexOf(acceptableIssuers, issuer) != -1)
                        return certificate;
                }
            }
            if (localCertificates != null &&
                localCertificates.Count > 0)
                return localCertificates[0];

            return null;
        }

    }
Developer technologies C#
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