Hm.  Interesting predicament.  Two thoughts:

If the goal is to allow clients to note and obey the 'strict' directive
even in the face of a SSL Interception proxy... what you propose won't
work. The proxies will be built to just remove the strict directive, or
the header all together.

If the organization running the proxy wanted to block access to the site
in question, they would do so. If they want to monitor ongoing access,
they will strip the directive/header so the clients continue to connect.
If they are ambivalent - 'access it or not, we don't care, but must
monitor you if you do' - the stripping feature may or may not be enabled.

What you propose would only help in the latter case, it will not
actually provide more security if the website considers the proxy to be
an adversary. And if they add the strict header, I would imagine that
the website does consider them to be an adversary, or at least that they
do not wish the connection to succeed..

So I don't think what you propose is worthwhile, specifically because it
does add risk via sites bricking themselves, while not improving
security considerably.




As far as the laptop moving between home and work... I get the
impression this situation may be regarded as a 'failure' of the
protocol. That is, we have unintentionally broke something.  I disagree.
I think the situation has worked as desired.

Because if we replace the players with a rogue government performing TLS
MitM, with the specific goal of isolating clients from receiving
up-to-date security policies... we would declare this same situation a
success.

I don't see a way to reconcile the two situations, as they behave almost
exactly the same.

TLS Proxies add a third player into what was previously a (primarily)
two-party protocol*. I think the strict directive preserves the
reasonable property that any one of the three parties can choose not to
participate based on the settings of the protocol.
 - The TLS proxy can block access or choose not to intercept
 - The user can not visit the site
 - The site can declare "I don't want anyone else seeing the data I
consider to be for the user's eyes only"

I expect that Firefox and Google may even continue to preload entries in
their browsers that apply the 'strict' directive specifically to provide
websites the power to assert their right to a MitM-free connection. I
know several websites who would like to exercise that right.


-tom

* Yes yes, CAs make 3, but that's PKIX, not TLS.

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