Su ayuda porfavor tengo un server squid configurado de la siguiente forma

# Configuracion del Squid

# Puertos
http_port 8080 transparent
http_port 3128 transparent
icp_port 3130

# No cache
acl QUERY urlpath_regex cgi-bin \?

no_cache deny QUERY

# Memory
cache_mem 512 MB

# Politica de Cache
cache_replacement_policy heap GDSF
memory_replacement_policy heap GDSF

# Disco
cache_dir diskd /var/spool/squid 4000 16 256

# Logs
cache_log /var/log/squid/cache.log
cache_access_log /var/log/squid/access.log
cache_store_log /var/log/squid/store.log
cache_swap_log /var/log/squid/swap.log
logfile_rotate 10

redirect_rewrites_host_header off
tcp_outgoing_tos 0x20

# ACL
acl all src 0.0.0.0/0.0.0.0
acl manager proto cache_object
acl localhost src 127.0.0.1/255.255.255.255

#acl de ip
acl restringidos src "/etc/squid/reglas/restringidos"
acl navtotal src "/etc/squid/reglas/permitidos"

#acl paginas
acl sitiospermitidos url_regex "/etc/squid/reglas/sitiospermitidos"
#acl sri url_regex "/etc/squid/reglas/permiSRI.txt"
#acl fmf url_regex "/etc/squid/reglas/permiFMF.txt"
#acl ippf url_regex "/etc/squid/reglas/permiIPPF.txt"

#acl de puertos
acl to_localhost dst 127.0.0.0/8
acl SSL_ports port 443 563
acl Safe_ports port 80 # http
acl Safe_ports port 21 # ftp
acl Safe_ports port 443 563 # https, snews
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 CONNECT method CONNECT

#acl programas
acl prog req_mime_type -i ^application/octet-stream$ ^application/x-javascript$ ^application/x-epf$ ^application/pdf$

http_access allow manager localhost
http_access deny manager

http_access deny !Safe_ports
http_access deny CONNECT !SSL_ports

#acplicar los acl
http_access allow localhost
http_access allow restringidos sitiospermitidos
http_access allow navtotal

#deniega todo
http_access deny all

maximum_object_size 60096 KB
store_avg_object_size 50 KB

# User
cache_effective_user squid
cache_effective_group squid

visible_hostname proxy-vpn

log_icp_queries off
buffered_logs on

y corro las siguientes reglas para hacerlo transparente
iptables -t nat -A PREROUTING -i eth0 -p tcp --dport 80 -j REDIRECT --to-port 3128
iptables -P FORWARD ACCEPT
iptables -P OUTPUT ACCEPT
iptables -P INPUT ACCEPT
echo 1 > /proc/sys/net/ipv4/ip_forward
iptables --table nat --append POSTROUTING --out-interface eth1 -j MASQUERADE
iptables --append FORWARD --in-interface eth0 -j ACCEPT
iptables -A INPUT -s 0.0.0.0/0 -p tcp --dport 25 -j ACCEPT
iptables -A INPUT -s 0.0.0.0/0 -p tcp --dport 110 -j ACCEPT
iptables -A FORWARD -s 172.16.1.1/24 -i eth1 -p tcp --dport 25 -j ACCEPT
iptables -A FORWARD -s 192.16.1.1/24 -i eth2 -p udp --dport 110 -j ACCEPT
iptables -F
iptables -X
iptables -Z
iptables -t nat -F
iptables -t nat -P PREROUTING ACCEPT
iptables -t nat -A POSTROUTING -o eth0 -j MASQUERADE
iptables -A FORWARD -p tcp --dport 25 -j ACCEPT
iptables -A FORWARD -p tcp --dport 110 -j ACCEPT
service iptables save

todo funciona ok, el problema es q no puedo agregar a hotmail a los sitios permitidos por q el squid me rechaza la coneccion segura q hace al tratar de conectarse por el puerto 443 me podrian ayudar por favor