A student at school is working on getting Alexa working on a Raspberry
Pi. I've done it on one of my Pis and it works at home, but not at
school, I think because of the school web proxy. There seems to be a
paucity of information about proxy settings for Alexa, and it doesn't
appear to respect the system proxy settings in /etc/environment.

The Pi network is behind a Shorewall firewall to protect the school
network. So in a flash of inspiration, I thought I could simply DNAT the
http requests hitting Shorewall as default gateway, so automatically
redirecting them to the school proxy. That works for http, but not for
https.

After a little bit of digging to find out how a proxy functions for
https it became obvious that  a simplistic DNAT couldn't work. It seems
that a browser, knowing that it's going through a browser, first sends
an unencrypted http CONNECT command before negotiating the ssl tunnel.

But would it be possible to somehow configure Shorewall, on receipt of a
tcp:443 connection request, to inject the CONNECT command into the
stream before starting to relay the ssl dialogue, quoting the pre-DNAT
destination ip address? How (in outline) could you achieve that?

Regards - Philip

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