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Given the following section in Web.Config : <system.net> <mailSettings> <smtp deliveryMethod="Network" from="SomeWebsite Admin &lt;someuser@gmail.com&gt;"> <network host="smtp.gmail.com" port="587" defaultCredentials="true" userName="someuser@gmail.com" password="somepassword" /> </smtp> </mailSettings> </system.net> And the following code snippet: smtp = new SmtpClient(); smtp.Host = "smtp.gmail.com"; smtp.Port = 587; smtp.EnableSsl = true; smtp.DeliveryMethod = SmtpDeliveryMethod.Network; smtp.UseDefaultCredentials = false; smtp.Credentials = new NetworkCredential( "someuser@gmail.com", "somepassword" ); smtp.Send( mailMessage ); The above works fine, however commenting out the programmatic overrides, like this: smtp = new SmtpClient(); //smtp.Host = "smtp.gmail.com"; //smtp.Port = 587; smtp.EnableSsl = true; //smtp.DeliveryMethod = SmtpDeliveryMethod.Network; //smtp.UseDefaultCredentials = false; //smtp.Credentials = new NetworkCredential( "someuser@gmail.com", "somepassword" ); smtp.Send( mailMessage ); fails with: System.Net.Mail.SmtpException: {"The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.5.1 Authentication Required. Learn more at "} Yes, the blank space after the "learn more at" is really there, and it makes things extra fun. Thing is, I can't be hardcoding these values, as they change from development to internal staging to live. So I'm wondering why it appears to fail to

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