>What if I want to send sensitive information about delivery failures? I.e. the 
>way a MITM was attempted?

It's probably not a great idea to send that kind of info unless you
already have a relationship with the recipient. 

>See above. Opportunistic TLS is the wrong approach here in my opinion. I never 
>liked it and I never will. I think the reasons
>are obvious.

Exactly.  If you want to receive stuff securely, you need to publish
an end-to-end encryption key, most likely PGP or S/MIME.  Of course,
then there's the question of how you know the key was published
securely and you're already halfway down the rabbit hole.  I suppose
you could try to go with https, but it's got its own MITM problems
with overly compliant CAs issuing wildcard certs to parties you and I
don't think should have them.

DMARC experience suggests that you should send routine stuff using
automated processes, and if there's something really interesting,
make arrangements with the other party.

R's,
John

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