[squid-users] SSL bump working on most site...cert pinning issue?

From: James Lay <jlay_at_slave-tothe-box.net>
Date: Mon, 30 Jun 2014 06:38:46 -0600

Topic pretty much says it...most sites work fine using my below set up,
but some (Apple's app store) do not. I'm wondering if cert pinning is
the issue? Since this set up is basically two separate sessions, I
packet captured both. The side the I have control over gives me a TLS
Record Layer Alert Close Notify. I am unable to decrypt the other side
as the device in question is an iDevice and I can't capture the master

I've even tried to ACL certain sites to not bump, but they don't go
through. Below is my complete setup. This is running the below:

Squid Cache: Version 3.4.6
configure options: '--prefix=/opt' '--enable-icap-client'
'--enable-ssl' '--enable-linux-netfilter'
'--enable-follow-x-forwarded-for' '--with-large-files'

Any assistance with troubleshooting would be wonderful...thank you.


$IPTABLES -t nat -A PREROUTING -i eth0 -s -p tcp --dport
80 -j REDIRECT --to-port 3128
$IPTABLES -t nat -A PREROUTING -i eth0 -s -p tcp --dport
443 -j REDIRECT --to-port 3129

acl localnet src

acl SSL_ports port 443
acl Safe_ports port 80 # http
acl Safe_ports port 21 # ftp
acl Safe_ports port 443 # https
acl Safe_ports port 70 # gopher
acl Safe_ports port 210 # wais
acl Safe_ports port 1025-65535 # unregistered ports
acl Safe_ports port 280 # http-mgmt
acl Safe_ports port 488 # gss-http
acl Safe_ports port 591 # filemaker
acl Safe_ports port 777 # multiling http

acl broken_sites dstdomain textnow.me
acl broken_sites dstdomain akamaiedge.net
acl broken_sites dstdomain akamaihd.net
acl broken_sites dstdomain apple.com
acl allowed_sites url_regex "/opt/etc/squid/url.txt"
acl all_others dst all
acl SSL method CONNECT

http_access deny !Safe_ports
http_access deny CONNECT !SSL_ports

http_access allow manager localhost
http_access deny manager

http_access allow allowed_sites
http_access deny all_others
http_access allow localnet
http_access allow localhost

http_access deny all
icp_access deny all

sslproxy_cert_error allow broken_sites
sslproxy_cert_error deny all

sslproxy_options ALL
ssl_bump none broken_sites
ssl_bump server-first all

http_port intercept
https_port intercept ssl-bump
generate-host-certificates=on cert=/opt/sslsplit/sslsplit.crt
key=/opt/sslsplit/sslsplitca.key options=ALL sslflags=NO_SESSION_REUSE

always_direct allow all

hierarchy_stoplist cgi-bin ?

access_log syslog:daemon.info common

refresh_pattern ^ftp: 1440 20% 10080
refresh_pattern ^gopher: 1440 0% 1440
refresh_pattern -i (cgi-bin|\?) 0 0% 0
refresh_pattern . 0 20% 4320

icp_port 3130

coredump_dir /opt/var
Received on Mon Jun 30 2014 - 12:38:54 MDT

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