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POHow can I send emails through SSL SMTP with the .NET Framework?
 

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    <p>Is there a way with the .NET Framework to send emails through an SSL SMTP server on port 465?</p> <p>The usual way:</p> <pre><code>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); </code></pre> <p>times out:</p> <pre><code>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() -&gt; 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() -&gt; 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 </code></pre> <p>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 STARTDLS then switches to an Encrypted connection: RFC 2228), but doesn't support Implicit SSL (entire connection is wrapped in an SSL layer)...</p>
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    1. CO[SmtpClient.EnableSsl Property](http://msdn.microsoft.com/en-us/library/system.net.mail.smtpclient.enablessl.aspx) "An alternate connection method is where an SSL session is established up front before any protocol commands are sent. This connection method is sometimes called SMTP/SSL, SMTP over SSL, or SMTPS and by default uses port 465. This alternate connection method using SSL is not currently supported." FWIW
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