*   Client <-> Middlebox <-> Client-facing server <-> Backend server


  *   With "Middlebox" really meaning a middlebox like a firewall or similar.

The middlebox is not allowed to modify traffic between the client and the 
server. Doing so would mean that the packets the client sent are not the ones 
that the server received, and the two message digests would disagree.  (If you 
think about things, it *has* to be this way, otherwise TLS would not be able to 
provide integrity guarantees.)


  *   From the draft, ECH seems to be designed to still allow successful TLS 
connection establishment if the encrypted_client_hello extension is dropped 
from the ClientHello on a conforming middlebox. Provided that the middlebox is 
authoritative for the client-facing server's public name, as reported/delivered 
by DNS to the client. We can assume that this is the case here.

I do not understand what you mean by this.  The word “authoritative” is used to 
mean that it has a certificate and keypair and can do TLS termination. DNS 
giving the client a particular IP address is not authoritative. It can be 
confusing because DNS terminology uses authoritative to mean that a particular 
entity can prepare data used for DNS responses.  But it is not authoritative in 
the TLS sense.

I think your questions can be answered with those two overall corrections 
above.  If not, please continue the thread.  (And feel free to repost from your 
note since I trimmed for brevity.)

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