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copied!<p>I ran in to this problem a while ago as well. The problem is that SmtpClient does not support implicit SSL connections, but does support explicit connections (<a href="http://blogs.msdn.com/b/webdav_101/archive/2008/06/02/system-net-mail-with-ssl-to-authenticate-against-port-465.aspx" rel="noreferrer">System.Net.Mail with SSL to authenticate against port 465</a>). The previous class of MailMessage (I believe .Net 1.0) did support this but has long been obsolete.</p> <p>My answer was to call the CDO (Collaborative Data Objects) (<a href="http://support.microsoft.com/kb/310212" rel="noreferrer">http://support.microsoft.com/kb/310212</a>) directly through COM using something like the following:</p> <pre><code> /// <summary> /// Send an electronic message using the Collaboration Data Objects (CDO). /// </summary> /// <remarks>http://support.microsoft.com/kb/310212</remarks> private void SendTestCDOMessage() { try { string yourEmail = "YourUserName@gmail.com"; CDO.Message message = new CDO.Message(); CDO.IConfiguration configuration = message.Configuration; ADODB.Fields fields = configuration.Fields; Console.WriteLine(String.Format("Configuring CDO settings...")); // Set configuration. // 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. (Hint: This requires the use of "sendusername" and "sendpassword" fields) // - cdoNTLM, value 2. The current process security context is used to authenticate with the service. ADODB.Field field = fields["http://schemas.microsoft.com/cdo/configuration/smtpserver"]; field.Value = "smtp.gmail.com"; field = fields["http://schemas.microsoft.com/cdo/configuration/smtpserverport"]; field.Value = 465; field = fields["http://schemas.microsoft.com/cdo/configuration/sendusing"]; field.Value = CDO.CdoSendUsing.cdoSendUsingPort; field = fields["http://schemas.microsoft.com/cdo/configuration/smtpauthenticate"]; field.Value = CDO.CdoProtocolsAuthentication.cdoBasic; field = fields["http://schemas.microsoft.com/cdo/configuration/sendusername"]; field.Value = yourEmail; field = fields["http://schemas.microsoft.com/cdo/configuration/sendpassword"]; field.Value = "YourPassword"; field = fields["http://schemas.microsoft.com/cdo/configuration/smtpusessl"]; field.Value = "true"; fields.Update(); Console.WriteLine(String.Format("Building CDO Message...")); message.From = yourEmail; message.To = yourEmail; message.Subject = "Test message."; message.TextBody = "This is a test message. Please disregard."; Console.WriteLine(String.Format("Attempting to connect to remote server...")); // Send message. message.Send(); Console.WriteLine("Message sent."); } catch (Exception ex) { Console.WriteLine(ex.Message); } } </code></pre> <p>Do not forget to browse through your COM references and add the "Microsoft CDO for Windows 200 Library" which should add two references: ADODB, and CDO.</p>

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