On Thu 2018-03-22 15:17:18 -0400, Viktor Dukhovni wrote:
>> On Mar 22, 2018, at 2:59 PM, Martin Thomson <[email protected]> wrote:
>> 
>> https://tools.ietf.org/html/draft-trammell-optional-security-not-00 is 
>> relevant. 
>
> A reasonable guiding principle, but sometimes *availability* trumps security.
> This is sufficiently often the case with email to make explicit preference for
> delivery above all other concerns a necessary feature.
>
> When a user gets a delay warning for their initial attempt to send a 
> time-sensitive
> message, it should be possible to resend the message with an explicit opt-out 
> of
> enhanced security protections (beyond unauthenticated opportunistic STARTTLS).

can't they opt-out by re-sending to their submission agent without the
REQUIRETLS SMTP command?  or is the fear that their submission agent
will invoke REQUIRETLS on the next hop without the user's permission?

fwiw, i think troubleshooting alone might be sufficient reason to
document the "RequireTLS: NO" message header, but i'm pretty unclear on
any sane UI/UX story for how a troubleshooter manages to introduce it --
it's pretty much expert feature territory (e.g. those of us who edit our
message headers by hand).

     --dkg

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