Question

Is there a way with the .NET Framework to send emails through an SSL SMTP server on port 465?

The usual way:

System.Net.Mail.SmtpClient _SmtpServer = new System.Net.Mail.SmtpClient("tempurl.org");
_SmtpServer.Port = 465;
_SmtpServer.EnableSsl = true;
_SmtpServer.Credentials = new System.Net.NetworkCredential("username", "password");
_SmtpServer.Timeout = 5000;
_SmtpServer.UseDefaultCredentials = false;

MailMessage mail = new MailMessage();
mail.From = new MailAddress(from);
mail.To.Add(to);
mail.CC.Add(cc);
mail.Subject = subject;
mail.Body = content;
mail.IsBodyHtml = useHtml;
_SmtpServer.Send(mail);

times out:

System.Net Verbose: 0 : [1024] SmtpClient::.ctor(host=ssl0.ovh.net, port=465)
System.Net Information: 0 : [1024] Associating SmtpClient#64923656 with SmtpTransport#44624228
System.Net Verbose: 0 : [1024] Exiting SmtpClient::.ctor()  -> SmtpClient#64923656
System.Net Information: 0 : [1024] Associating MailMessage#17654054 with Message#52727599
System.Net Verbose: 0 : [1024] SmtpClient#64923656::Send(MailMessage#17654054)
System.Net Information: 0 : [1024] SmtpClient#64923656::Send(DeliveryMethod=Network)
System.Net Information: 0 : [1024] Associating SmtpClient#64923656 with MailMessage#17654054
System.Net Information: 0 : [1024] Associating SmtpTransport#44624228 with SmtpConnection#14347911
System.Net Information: 0 : [1024] Associating SmtpConnection#14347911 with ServicePoint#51393439
System.Net.Sockets Verbose: 0 : [1024] Socket#26756241::Socket(InterNetwork#2)
System.Net.Sockets Verbose: 0 : [1024] Exiting Socket#26756241::Socket() 
System.Net.Sockets Verbose: 0 : [1024] Socket#23264094::Socket(InterNetworkV6#23)
System.Net.Sockets Verbose: 0 : [1024] Exiting Socket#23264094::Socket() 
System.Net.Sockets Verbose: 0 : [1024] Socket#26756241::Connect(20:465#337754884)
System.Net.Sockets Verbose: 0 : [1024] Exiting Socket#26756241::Connect() 
System.Net.Sockets Verbose: 0 : [1024] Socket#23264094::Close()
System.Net.Sockets Verbose: 0 : [1024] Socket#23264094::Dispose()
System.Net.Sockets Verbose: 0 : [1024] Exiting Socket#23264094::Close() 
System.Net Information: 0 : [1024] Associating SmtpConnection#14347911 with SmtpPooledStream#14303791
System.Net.Sockets Verbose: 0 : [1024] Socket#26756241::Receive()
System.Net.Sockets Verbose: 0 : [2404] Socket#26756241::Dispose()
System.Net.Sockets Error: 0 : [1024] Exception in the Socket#26756241::Receive - A blocking operation was interrupted by a call to WSACancelBlockingCall
System.Net.Sockets Verbose: 0 : [1024] Exiting Socket#26756241::Receive()   -> 0#0
System.Net Error: 0 : [1024] Exception in the SmtpClient#64923656::Send - Unable to read data from the transport connection: A blocking operation was interrupted by a call to WSACancelBlockingCall.
System.Net Error: 0 : [1024]    at System.Net.Sockets.NetworkStream.Read(Byte[] buffer, Int32 offset, Int32 size)
   at System.Net.DelegatedStream.Read(Byte[] buffer, Int32 offset, Int32 count)
   at System.Net.BufferedReadStream.Read(Byte[] buffer, Int32 offset, Int32 count)
   at System.Net.Mail.SmtpReplyReaderFactory.ReadLines(SmtpReplyReader caller, Boolean oneLine)
   at System.Net.Mail.SmtpReplyReaderFactory.ReadLine(SmtpReplyReader caller)
   at System.Net.Mail.SmtpConnection.GetConnection(String host, Int32 port)
   at System.Net.Mail.SmtpTransport.GetConnection(String host, Int32 port)
   at System.Net.Mail.SmtpClient.GetConnection()
   at System.Net.Mail.SmtpClient.Send(MailMessage message)
System.Net Verbose: 0 : [1024] Exiting SmtpClient#64923656::Send() 
System.Net Information: 0 : [1024] Associating MailMessage#49584532 with Message#19699911

I googled around and found that System.Net.Mail supports connections on port 587 (default port for Explicit SSL that starts unencrypted then issues a STARTTLS then switches to an Encrypted connection: RFC 2228), but doesn’t support Implicit SSL (entire connection is wrapped in an SSL layer) …

Answer 1

Here is an example of how to send email through GMail which also uses SSL/465. Minor tweaking of the code below should work!

using System.Web.Mail;
using System;
public class MailSender
{
    public static bool SendEmail(
        string pGmailEmail, 
        string pGmailPassword, 
        string pTo, 
        string pSubject,
        string pBody, 
        System.Web.Mail.MailFormat pFormat,
        string pAttachmentPath)
    {
    try
    {
        System.Web.Mail.MailMessage myMail = new System.Web.Mail.MailMessage();
        myMail.Fields.Add
            ("http://schemas.microsoft.com/cdo/configuration/smtpserver",
                          "smtp.gmail.com");
        myMail.Fields.Add
            ("http://schemas.microsoft.com/cdo/configuration/smtpserverport",
                          "465");
        myMail.Fields.Add
            ("http://schemas.microsoft.com/cdo/configuration/sendusing",
                          "2");
        //sendusing: cdoSendUsingPort, value 2, for sending the message using 
        //the network.

        //smtpauthenticate: Specifies the mechanism used when authenticating 
        //to an SMTP 
        //service over the network. Possible values are:
        //- cdoAnonymous, value 0. Do not authenticate.
        //- cdoBasic, value 1. Use basic clear-text authentication. 
        //When using this option you have to provide the user name and password 
        //through the sendusername and sendpassword fields.
        //- cdoNTLM, value 2. The current process security context is used to 
        // authenticate with the service.
        myMail.Fields.Add
        ("http://schemas.microsoft.com/cdo/configuration/smtpauthenticate","1");
        //Use 0 for anonymous
        myMail.Fields.Add
        ("http://schemas.microsoft.com/cdo/configuration/sendusername",
            pGmailEmail);
        myMail.Fields.Add
        ("http://schemas.microsoft.com/cdo/configuration/sendpassword",
             pGmailPassword);
        myMail.Fields.Add
        ("http://schemas.microsoft.com/cdo/configuration/smtpusessl",
             "true");
        myMail.From = pGmailEmail;
        myMail.To = pTo;
        myMail.Subject = pSubject;
        myMail.BodyFormat = pFormat;
        myMail.Body = pBody;
        if (pAttachmentPath.Trim() != "")
        {
            MailAttachment MyAttachment = 
                    new MailAttachment(pAttachmentPath);
            myMail.Attachments.Add(MyAttachment);
            myMail.Priority = System.Web.Mail.MailPriority.High;
        }

        System.Web.Mail.SmtpMail.SmtpServer = "smtp.gmail.com:465";
        System.Web.Mail.SmtpMail.Send(myMail);
        return true;
    }
    catch (Exception ex)
    {
        throw;
    }
}
}