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I'm running an SMTP server through IIS 6.0 on my Windows 2012 Server, and would like to make delivery of emails to be encrypted.

I have attached an SSL certificate to the server and set Require TLS encryption on the main "Access" page.

Image of dialog box

I have also enabled the "TLS encryption" checkbox in the "Delivery", "Outbound Security" tab shown here.

here.

I'm still getting emails through unencrypted.

What can I do to make delivery of emails encrypted?

Aki
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  • I'm almost certain this is not what tls is for in regards to smtp. TLS is an authentication type, designed to secure your connection with the server. But, it is not designed for sending out encrypted emails. I can think of several reasons why this wouldn't work, but I have no sources to back up this claim. – Naryna Apr 28 '16 at 19:10
  • So there is no way to send encrypted email messages via IIS 6.0 SMTP? – Aki Apr 28 '16 at 19:35
  • Encryption defeats the purpose of email. There is no way for the server on the other side to know the key needed to decrypt it. If there was, email servers would have tremendous overhead. Think about the number of public/private keys that would have to be kept because communications with every other email server are possible and they would all have to support the same standard. As reference [take a look at the definition of TLS](http://searchsecurity.techtarget.com/definition/Transport-Layer-Security-TLS) – Naryna Apr 28 '16 at 19:38
  • I get what you're saying Brandyn... but encryption does not defeat the purpose of email. Encrypting communications between mail servers is a worthwile venture, as is encrypting message contents themselves for the intended recipient, although yes, these are 2 seperate undertakings. – Dylan Knoll Apr 28 '16 at 20:21
  • What I'm finding difficult to understand is how services such as Mandrill send emails encrypted in that case? Email send from my servers, show an unlocked padlock, and Gmail refers me to this page: https://support.google.com/mail/answer/6330403?p=tls&hl=en&rd=1. How do they do it then? – Aki Apr 29 '16 at 08:24

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