title: Is it possible to enforce encrypted SMTP for certain recipients?
body: <p>I'm trying to understand how to send encrypted email from an ASP.NET application using an SMTP server set up on IIS. Apologies in advance if I'm not being clear - I'm fundamentally a programmer and my understanding of email is limited.</p>
  
  <p>I know that the SMTP server can be configured to insist on TLS/SSL encryption. What I'm not clear about is how this works with the <code>EnableSsl</code> property of <code>System.Net.Mail.SmtpClient()</code> and the implications when sending to recipients which don't support encryption.</p>
  
  <p>My goal is to ensure that emails sent to certain recipients are always encrypted, but I don't want emails to fail when sent to other recipients whose receiving SMTP servers don't support encrypted messages.</p>
  
  <p>Is it possible therefore to use SSL conditionally in my scenario based on the intended recipient?</p>