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Bug that could be described as an erratic behaviour in squid https filtering : some websites specified in squidgard target categories pass through the web filtering, and some don't.

Investigations using a very simplified pfsense configuration as follows :
- fresh install of pfsense 2.5.2 whith only squid and squidguard installed
- squid with default configuration, transparent mode and SSL man in the middle filtering activated (with an internal CA created through the certificate manager with default parameters)
- squidguard : created a target categorie with two URLs, parisaeroport.fr and visitstrasbourg.fr, and denying this in Common ACL target rules list.

Result : parisaeroport.fr is blocked as intended, but visitstrasbourg.fr is not blocked at all, without any clear records in squid logs that could highlight that difference.
It is not a cache problem.

Squidguard configuration file :

# ============================================================
# SquidGuard configuration file
# This file generated automaticly with SquidGuard configurator
# (C)2006 Serg Dvoriancev
# email: dv_serg@mail.ru
# ============================================================

logdir /var/squidGuard/log
dbhome /var/db/squidGuard

# 
dest target_test {
    domainlist target_test/domains
    log block.log
}

# 
rew safesearch {
    s@(google..*/search?.*q=.*)@&safe=active@i
    s@(google..*/images.*q=.*)@&safe=active@i
    s@(google..*/groups.*q=.*)@&safe=active@i
    s@(google..*/news.*q=.*)@&safe=active@i
    s@(yandex..*/yandsearch?.*text=.*)@&fyandex=1@i
    s@(search.yahoo..*/search.*p=.*)@&vm=r&v=1@i
    s@(search.live..*/.*q=.*)@&adlt=strict@i
    s@(search.msn..*/.*q=.*)@&adlt=strict@i
    s@(.bing..*/.*q=.*)@&adlt=strict@i
    s@(duckduckgo..*/?.*q=.*)@&kp=1@i
    s@(rambler..*/?.*query=.*)@&adult=family@i
    s@(qwant..*/?.*q=.*)@&s=2@i
    s@(ecosia..*/search.*q=.*)@&safesearch=2@i
    s@(onesearch..*/yhs/search.*)@&vm=r@i
    log block.log
}

# 
acl  {
    # 
    default  {
        pass !target_test all
        redirect http://192.168.10.9:80/sgerror.php?url=403%20&a=%a&n=%n&i=%i&s=%s&t=%t&u=%u
        log block.log
    }
}

Squid configuration :

# This file is automatically generated by pfSense
# Do not edit manually !

http_port 192.168.10.9:3128 ssl-bump generate-host-certificates=on dynamic_cert_mem_cache_size=10MB cert=/usr/local/etc/squid/serverkey.pem cafile=/usr/local/share/certs/ca-root-nss.crt 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:!3DES:!SHA1:!MD5:!EXP:!PSK:!SRP:!DSS tls-dh=prime256v1:/etc/dh-parameters.2048 options=NO_SSLv3,NO_TLSv1,SINGLE_DH_USE,SINGLE_ECDH_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 cafile=/usr/local/share/certs/ca-root-nss.crt 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:!3DES:!SHA1:!MD5:!EXP:!PSK:!SRP:!DSS tls-dh=prime256v1:/etc/dh-parameters.2048 options=NO_SSLv3,NO_TLSv1,SINGLE_DH_USE,SINGLE_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 cafile=/usr/local/share/certs/ca-root-nss.crt 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:!3DES:!SHA1:!MD5:!EXP:!PSK:!SRP:!DSS tls-dh=prime256v1:/etc/dh-parameters.2048 options=NO_SSLv3,NO_TLSv1,SINGLE_DH_USE,SINGLE_ECDH_USE

icp_port 0
digest_generation off
dns_v4_first off
pid_filename /var/run/squid/squid.pid
cache_effective_user squid
cache_effective_group proxy
error_default_language fr
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/security_file_certgen -s /var/squid/lib/ssl_db -M 4MB -b 2048
tls_outgoing_options cafile=/usr/local/share/certs/ca-root-nss.crt
tls_outgoing_options capath=/usr/local/share/certs/
tls_outgoing_options options=NO_SSLv3,NO_TLSv1,SINGLE_DH_USE,SINGLE_ECDH_USE
tls_outgoing_options 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:!SHA1:!MD5:!EXP:!PSK:!SRP:!DSS
sslcrtd_children 5

logfile_rotate 0
debug_options rotate=0
shutdown_lifetime 3 seconds
# Allow local network(s) on interface(s)
acl localnet src  192.168.10.0/24
forwarded_for on
uri_whitespace strip

acl dynamic urlpath_regex cgi-bin ?
cache deny dynamic

cache_mem 64 MB
maximum_object_size_in_memory 256 KB
memory_replacement_policy heap GDSF
cache_replacement_policy heap LFUDA
minimum_object_size 0 KB
maximum_object_size 4 MB
cache_dir ufs /var/squid/cache 100 16 256
offline_mode off
cache_swap_low 90
cache_swap_high 95
cache deny all
# Add any of your own refresh_pattern entries above these.
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

#Remote proxies

# Setup some default acls
# ACLs all, manager, localhost, and to_localhost are predefined.
acl allsrc src all
acl safeports port 21 70 80 210 280 443 488 563 591 631 777 901  3128 3129 1025-65535 
acl sslports port 443 563  

acl purge method PURGE
acl connect method CONNECT

# Define protocols used for redirects
acl HTTP proto HTTP
acl HTTPS proto HTTPS

# SslBump Peek and Splice
# http://wiki.squid-cache.org/Features/SslPeekAndSplice
# http://wiki.squid-cache.org/ConfigExamples/Intercept/SslBumpExplicit
# Match against the current step during ssl_bump evaluation [fast]
# Never matches and should not be used outside the ssl_bump context.
#
# At each SslBump step, Squid evaluates ssl_bump directives to find
# the next bumping action (e.g., peek or splice). Valid SslBump step
# values and the corresponding ssl_bump evaluation moments are:
#   SslBump1: After getting TCP-level and HTTP CONNECT info.
#   SslBump2: After getting TLS Client Hello info.
#   SslBump3: After getting TLS Server Hello info.
# These ACLs exist even when 'SSL/MITM Mode' is set to 'Custom' so that
# they can be used there for custom configuration.
acl step1 at_step SslBump1
acl step2 at_step SslBump2
acl step3 at_step SslBump3
http_access allow manager localhost

http_access deny manager
http_access allow purge localhost
http_access deny purge
http_access deny !safeports
http_access deny CONNECT !sslports

# Always allow localhost connections
http_access allow localhost

request_body_max_size 0 KB
delay_pools 1
delay_class 1 2
delay_parameters 1 -1/-1 -1/-1
delay_initial_bucket_level 100
delay_access 1 allow allsrc

# Reverse Proxy settings

# Package Integration
url_rewrite_program /usr/local/bin/squidGuard -c /usr/local/etc/squidGuard/squidGuard.conf
url_rewrite_bypass off
url_rewrite_children 16 startup=8 idle=4 concurrency=0

# Custom options before auth

# Set YouTube safesearch restriction
acl youtubedst dstdomain -n www.youtube.com m.youtube.com youtubei.googleapis.com youtube.googleapis.com www.youtube-nocookie.com
request_header_access YouTube-Restrict deny all
request_header_add YouTube-Restrict none youtubedst
ssl_bump peek step1
ssl_bump bump all
# Setup allowed ACLs
# Allow local network(s) on interface(s)
http_access allow localnet
# Default block all to be sure
http_access deny allsrc