Thanks for the overview of a real problem, Andrew.
(I recall having to add an exception for a "Mozilla Root CA" to
access email at one time.)

Andrew Sutherland writes:

> I propose that we use a certificate-observatory-style mechanism to
> corroborate any invalid certificates by attempting the connection
> from 1 or more trusted servers whose identity can be authenticated
> using the existing CA infrastructure.

Although this can identify a MITM between the mail client and the
internet, I assume it won't identify one between the mail server
and the internet.

> *** "it looks like you are behind a corporate firewall that MITMs
> you, you should add the firewall's CA to your device.  Send the
> user to a support page to help walk them through these steps if
> that seems right."
> *** "it looks like the user is under attack"

I wonder how to distinguish these two situations and whether they
really should be distinguished.
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