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When using sp_send_dbmail to send an email on SQL Server, how do you specify that the email be sent in an encrypted format?

I found a thread discussing including the string "[SECURE]" in the subject line, but these comments are 8 years old and not backed up by any source.

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    How do you define secure? How do you want to encrypt it? PGP? It looks like the thread you linked to refers to an exchange plugin where a keyword in a subject makes sure the email is rewritten and shown in a web app
    – Tom V
    Commented Oct 2, 2018 at 11:41
  • @TomV In (for example) Outlook, there is an option to encrypt (apparently using DES) an outgoing email before it is sent. Is there a way to trigger this functionality from the parameters passed to sp_send_dbmail?
    – user161299
    Commented Oct 2, 2018 at 12:01
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    Maybe if you have the public key you can encrypt the body of the message yourself before sending it, I'm not sure which parts are encrypted and which are not by outlook. I have never done this though. As email from sp_send_dbmail is not sent through outlook I don't think you can piggy-back on the outlook functionality
    – Tom V
    Commented Oct 2, 2018 at 12:36

1 Answer 1

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I don't think SQL Server has any built-in functionality to achieve what you're after.

One possible solution is to use a local SMTP server as a relay, so that the email is not encrypted on the initial hop (between SQL Server and the local SMTP server), but it gets encrypted leveraging the SMTP server's functionalities on the second hop (to the outbound SMTP server).

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