On 15/02/2015 23:36, Alan Palmer wrote:
I'm trying to get squid 3.4.11 on openbsd 5.6 to act as a transparent
ssl proxy.

I've rebuilt squid with --enable-ssl-crtd, generated my own self signed
cert (ala http://www.akadia.com/services/ssh_test_certificate.html) and
have the following config lines:

Hey Alan,

What is the full output of "squid -v"?

I am unsure about the akadia tutorial.
Please take a look at:
http://wiki.squid-cache.org/EliezerCroitoru/Drafts/SSLBUMP

It contains some hints on how to create the certificate and contains a snippet of squid configuration to make a basic ssl-bump work(the echo command code might not be right)

I am pretty sure the certificate you have created is not the right type for the task.

Eliezer

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