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I am doing some research on man-in-the-middle focusing on SSL in particular.

I have been looking into generating a certificate on request when a client connects and requests a secured page.

Assuming that;

  • Client is connected to AP controlled by me and ignoring cert validation
  • AP is running airmon-ng and airbas-ng with DHCP.
  • OS is Debian on a Rasp Pi, that then forwards to the real WWW

Is it feasible to generate a certificate per request, and if so, are tools available for this, or would the request have to be scripted to sign a cert via OpenSSL, and logging the event.

Cheers

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I use mitmproxy (and HoneyProxy a graphical interface to it) at work to do that. Works perfectly.

Relevant part of the documentation about SSL: http://mitmproxy.org/doc/ssl.html

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Yes, it's possible.

10 seconds of googling gives you a link to the dynamic SSl generation feature of Squid and that links to the (necessary) SSLBump feature that implements the MITM attack itself.

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