Hey,

From this basic snippet of the email I can tell you:
1. using DNAT is wrong anyway for intercept proxy.
2. specifically for SSL-BUMP it's ^^^ the cause of most of your problems.

Since SSL-BUMP tries to to bump server first it should be able to knwo what server to bump while using DNAT you replace the dst IP + PORT with the proxy IP which makes it's impossible to "bump server first".

Use either REDIRECT or TPROXY instead to allow SSL-BUMP + server fisrt.

Eliezer

On 12/31/2012 2:37 PM, Swapneel Patnekar wrote:
Hello Everyone,

I've successfully managed to configure sslbump with
squid-3.HEAD-20121231-r12554.

However, I am having troubles in configuring SslBump using
Bump-Server-First in Transparent mode.  Basically I don't think I have
the correct set of directives/configuration parameters in squid.conf
to check/test SslBump using Bump-Server-First in Transparent mode. Any
help on making this work is much appreciated.

Redirecting traffic on port 80 & 443 to squid via iptables,

iptables -t nat -A PREROUTING -i $LAN_IN -p tcp --dport 80 -j DNAT
--to 192.168.2.1:3128
#iptables -t nat -A PREROUTING -i $LAN_IN -p tcp --dport 443 -j DNAT
--to 192.168.2.1:3129

Squid was compiled using the following flags,
./configure --enable-icap --enable-ssl --enable-ssl-crtd
--enable-delay-pools --with-openssl=/usr/local/openssl-1.0.0g

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