Imports Namespace=System.IO

Imports System.Net.Mail

Imports System.Security.Cryptography.X509Certificates

Imports System.Security.Cryptography.Pkcs

Class EncryptEmail

Shared Sub Main(ByVal args() As String)

  SendEncryptedEmail("test.pfx", "test.cer", """Somebody"" ", """Somebody"" ", "Test VB Encrypted HTML EMail", "This email is encrypted and signed.", "localhost", 25, False)

End Sub

    Shared Sub SendEncryptedEmail(ByVal SigningCertPath As String, ByVal EncryptingCertPath As String, ByVal [To] As String, ByVal From As String, ByVal Subject As String, ByVal Body As String, ByVal SmtpServer As String, ByVal SmtpPort As Integer, ByVal HTML As Boolean)

        Dim SignCert As New X509Certificate2(SigningCertPath, "password")

        Dim EncryptCert As New X509Certificate2(EncryptingCertPath, "")

        Dim Message As New StringBuilder()

        Message.AppendLine("Content-Type: text/" + IIf(HTML, "html", "plain") + "; charset=""iso-8859-1""") 'TODO: For performance reasons this should be changed to nested IF statements

        Message.AppendLine("Content-Transfer-Encoding: 7bit")

        Message.AppendLine()

        Message.AppendLine(Body)

        Dim BodyBytes As Byte() = Encoding.ASCII.GetBytes(Message.ToString())

        Dim ECms As New EnvelopedCms(New ContentInfo(BodyBytes))

        Dim Recipient As New CmsRecipient(SubjectIdentifierType.IssuerAndSerialNumber, EncryptCert)

        ECms.Encrypt(Recipient)

        Dim EncryptedBytes As Byte() = ECms.Encode()

        Dim Cms As New SignedCms(New ContentInfo(EncryptedBytes))

        Dim Signer As New CmsSigner(SubjectIdentifierType.IssuerAndSerialNumber, SignCert)

        Cms.ComputeSignature(Signer)

        Dim SignedBytes As Byte() = Cms.Encode()

        Dim Msg As New MailMessage()

        Msg.To.Add(New MailAddress([To]))

        Msg.From = New MailAddress(From)

        Msg.Subject = Subject

        Dim ms As New MemoryStream(EncryptedBytes)

        Dim av As New AlternateView(ms, "application/pkcs7-mime; smime-type=signed-data;name=smime.p7m")

        Msg.AlternateViews.Add(av)

        Dim smtp As New SmtpClient(SmtpServer, SmtpPort)

        smtp.UseDefaultCredentials = True

        smtp.Send(Msg)

    End Sub

End Class

using System;

using System.IO;

using System.Text;

using System.Net.Mail;

using System.Security.Cryptography.Pkcs;

using System.Security.Cryptography.X509Certificates;

namespace EncryptedSMIME

{

   class Program

   {

       static void Main(string[] args)

       {

           SendEncryptedEmail("Cert.pfx", "thawte.cer",

               ""Noah Body" ",

               ""John Doe" ",

               "Test C# Encrypted HTML EMail",

               "This email is encrypted and signed.",

               "smtp.singingeels.com", 25, false);

       }

       static void SendEncryptedEmail(

           string SigningCertPath, string EncryptingCertPath,

           string To, string From, string Subject, string Body,

           string SmtpServer, int SmtpPort, bool HTML)

       {

           X509Certificate2 SignCert = new X509Certificate2(SigningCertPath, "password");

           X509Certificate2 EncryptCert = new X509Certificate2(EncryptingCertPath, "");

           StringBuilder Message = new StringBuilder();

           Message.AppendLine("Content-Type: text/" + ((HTML) ? "html" : "plain") +

               "; charset="iso-8859-1"");

           Message.AppendLine("Content-Transfer-Encoding: 7bit");

           Message.AppendLine();

           Message.AppendLine(Body);

           byte[] BodyBytes = Encoding.ASCII.GetBytes(Message.ToString());

           EnvelopedCms ECms = new EnvelopedCms(new ContentInfo(BodyBytes));

           CmsRecipient Recipient = new CmsRecipient(

               SubjectIdentifierType.IssuerAndSerialNumber, EncryptCert);

           ECms.Encrypt(Recipient);

           byte[] EncryptedBytes = ECms.Encode();

           SignedCms Cms = new SignedCms(new ContentInfo(EncryptedBytes));

           CmsSigner Signer = new CmsSigner

               (SubjectIdentifierType.IssuerAndSerialNumber, SignCert);

           Cms.ComputeSignature(Signer);

           byte[] SignedBytes = Cms.Encode();

           MailMessage Msg = new MailMessage();

           Msg.To.Add(new MailAddress(To));

           Msg.From = new MailAddress(From);

           Msg.Subject = Subject;

           MemoryStream ms = new MemoryStream(EncryptedBytes);

           AlternateView av = new AlternateView(ms,

               "application/pkcs7-mime; smime-type=signed-data;name=smime.p7m");

           Msg.AlternateViews.Add(av);

           SmtpClient smtp = new SmtpClient(SmtpServer, SmtpPort);

           smtp.UseDefaultCredentials = true;

           smtp.Send(Msg);

       }

   }

}