Pfsense + Squid HTTPS Transparent

[macmagic]

Hi all,

I am new to PFSense - have been playing around with it on my home network a bit to get a better feel for it and hopefully use in production in the future.

Probably the millionth post about MITM HTTPS, but most other posts assume that pfsense is your firewall….

I have been struggling with Squid and transparent proxy for SSL. Transparent proxy works fine on HTTP, but as soon as I enable HTTPS - service wont start with error```
Bungled /usr/local/etc/squid/squid.conf line 6: https_port 127.0.0.1:3129 intercept

I am using ACME certificates and have successfully created the certificates needed for my domains.

This is how I have my network configured:

Unifi Security Gateway - Router, DHCP, Firewall, VLAN
PFSense ( - Firewall off entirely, WAN and LAN interface bridged, DNS Forwarder, DHCP Relay

DHCP: Gateway and DNS server set to PFSense box.

Can anyone shed some light on why this wont work?

[macmagic]

Anyone?

[Tantamount]

@macmagic:

I have been struggling with Squid and transparent proxy for SSL. Transparent proxy works fine on HTTP, but as soon as I enable HTTPS - service wont start with error```
Bungled /usr/local/etc/squid/squid.conf line 6: https_port 127.0.0.1:3129 intercept

Looking at my squid.conf file with Enable SSL filtering, I'm seeing a lot more content after the word "intercept."

https_port 127.0.0.1:3129 intercept ssl-bump generate-host-certificates=on dynamic_cert_mem_cache_size=10MB cert=/usr/local/etc/squid/serverkey.pem capath=/usr/local/share/certs
/ cipher=EECDH+ECDSA+AESGCM:EECDH+aRSA+AESGCM:EECDH+ECDSA+SHA384:EECDH+ECDSA+SHA256:EECDH+aRSA+SHA384:EECDH+aRSA+SHA256:EECDH+aRSA+RC4:EECDH:EDH+aRSA:!RC4:!aNULL:!eNULL:!LOW:!3D
ES:!MD5:!EXP:!PSK:!SRP:!DSS tls-dh=prime256v1:/etc/dh-parameters.2048 options=NO_SSLv2,NO_SSLv3,NO_TLSv1,SINGLE_DH_USE,SINGLE_ECDH_USE

Are you using the GUI to configure squid?

[ivancba]

i have some problem in lab.

Squid.conf transparent with self singned cert. Service is running

http_port 192.168.254.1:3128 ssl-bump generate-host-certificates=on dynamic_cert_mem_cache_size=10MB cert=/usr/local/etc/squid/serverkey.pem capath=/usr/local/share/certs/ cipher=EECDH+ECDSA+AESGCM:EECDH+aRSA+AESGCM:EECDH+ECDSA+SHA384:EE
CDH+ECDSA+SHA256:EECDH+aRSA+SHA384:EECDH+aRSA+SHA256:EECDH+aRSA+RC4:EECDH:EDH+aRSA:!RC4:!aNULL:!eNULL:!LOW:!3DES:!MD5:!EXP:!PSK:!SRP:!DSS tls-dh=prime256v1:/etc/dh-parameters.2048 options=NO_SSLv2,NO_SSLv3,NO_TLSv1,SINGLE_DH_USE,SINGLE_E
CDH_USE

http_port 127.0.0.1:3128 intercept ssl-bump generate-host-certificates=on dynamic_cert_mem_cache_size=10MB cert=/usr/local/etc/squid/serverkey.pem capath=/usr/local/share/certs/ cipher=EECDH+ECDSA+AESGCM:EECDH+aRSA+AESGCM:EECDH+ECDSA+SHA
384:EECDH+ECDSA+SHA256:EECDH+aRSA+SHA384:EECDH+aRSA+SHA256:EECDH+aRSA+RC4:EECDH:EDH+aRSA:!RC4:!aNULL:!eNULL:!LOW:!3DES:!MD5:!EXP:!PSK:!SRP:!DSS tls-dh=prime256v1:/etc/dh-parameters.2048 options=NO_SSLv2,NO_SSLv3,NO_TLSv1,SINGLE_DH_USE,SI
NGLE_ECDH_USE

https_port 127.0.0.1:3129 intercept ssl-bump generate-host-certificates=on dynamic_cert_mem_cache_size=10MB cert=/usr/local/etc/squid/serverkey.pem capath=/usr/local/share/certs/ cipher=EECDH+ECDSA+AESGCM:EECDH+aRSA+AESGCM:EECDH+ECDSA+SH
A384:EECDH+ECDSA+SHA256:EECDH+aRSA+SHA384:EECDH+aRSA+SHA256:EECDH+aRSA+RC4:EECDH:EDH+aRSA:!RC4:!aNULL:!eNULL:!LOW:!3DES:!MD5:!EXP:!PSK:!SRP:!DSS tls-dh=prime256v1:/etc/dh-parameters.2048 options=NO_SSLv2,NO_SSLv3,NO_TLSv1,SINGLE_DH_USE,S
INGLE_ECDH_USE

icp_port 0
digest_generation off
dns_v4_first on
pid_filename /var/run/squid/squid.pid
cache_effective_user squid
cache_effective_group proxy
error_default_language es
icon_directory /usr/local/etc/squid/icons
visible_hostname localhost
cache_mgr admin@localhost
access_log /var/squid/logs/access.log
cache_log /var/squid/logs/cache.log
cache_store_log none
netdb_filename /var/squid/logs/netdb.state
pinger_enable on
pinger_program /usr/local/libexec/squid/pinger
sslcrtd_program /usr/local/libexec/squid/ssl_crtd -s /var/squid/lib/ssl_db -M 4MB -b 2048
sslcrtd_children 5
sslproxy_capath /usr/local/share/certs/
sslproxy_options NO_SSLv2,NO_SSLv3,NO_TLSv1,SINGLE_DH_USE,SINGLE_ECDH_USE
sslproxy_cipher EECDH+ECDSA+AESGCM:EECDH+aRSA+AESGCM:EECDH+ECDSA+SHA384:EECDH+ECDSA+SHA256:EECDH+aRSA+SHA384:EECDH+aRSA+SHA256:EECDH+aRSA+RC4:EECDH:EDH+aRSA:!RC4:!aNULL:!eNULL:!LOW:!3DES:!MD5:!EXP:!PSK:!SRP:!DSS
sslproxy_flags DONT_VERIFY_PEER
sslproxy_cert_adapt setCommonName all

Squid.conf Transparent with ACME cert. Service stopped

http_port 192.168.254.1:3128
http_port 127.0.0.1:3128 intercept
https_port 127.0.0.1:3129 intercept
icp_port 0
digest_generation off
dns_v4_first on
pid_filename /var/run/squid/squid.pid
cache_effective_user squid
cache_effective_group proxy
error_default_language es
icon_directory /usr/local/etc/squid/icons
visible_hostname localhost
cache_mgr admin@localhost
access_log /var/squid/logs/access.log
cache_log /var/squid/logs/cache.log
cache_store_log none
netdb_filename /var/squid/logs/netdb.state
pinger_enable on
pinger_program /usr/local/libexec/squid/pinger

[doktornotor]

You CANNOT use ACME cert!!! You need your own cert. authority!!!