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Squid 2.7 STABLE8 (Win2008) can't get my MS Lync 2013 to work?

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We are using SQUID 2.7 STABLE8 on a Windows 2008 box, it is working except when a user tries to access Microsoft Lync 2013 they get a password prompt.

I've searched the web and spent countless hours on this with no luck, anyone able to shed some light?

When i start my Microsoft Lync 2013 client, on access.log I see the following hit when the proxy dialog box shows up within the Lync application.

1412717278.341    516 172.16.12.110 TCP_MISS/200 11695 CONNECT login.microsoftonline.com:443 - DIRECT/65.52.244.66 -

Here is my squid.conf file:

I've tried to add all of the published URLs and IPs that Microsoft lists for Office 365 and related products, but I still have no luck.. anyone able to assist?


# Port on which Squid will lisen on
http_port 8080

# Authentication
auth_param ntlm program c:/squid/libexec/mswin_ntlm_auth.exe --helper-protocol=squid-2.5-ntlmssp
auth_param ntlm children 5
auth_param ntlm keep_alive on
auth_param basic program c:/squid/libexec/mswin_ntlm_auth.exe --helper-protocol=squid-2.5-basic
auth_param basic children 5
auth_param basic realm Proxy Server
auth_param basic credentialsttl 2 hours
auth_param basic casesensitive off
authenticate_cache_garbage_interval 10 seconds

# Squid Defaults
acl all src all
acl manager proto cache_object
acl localhost src 127.0.0.1

# Class C Internal Subnet - Defaults
acl localnet src 10.0.0.0/8
acl localnet src 172.16.0.0/12
acl localnet src 192.168.0.0/16

# ACLs
# for destination machine
acl lan_dst dst 172.16.0.0/16
# for source machine
acl lan_src src 172.16.0.0/16
# for destination domain
acl lan_domain dstdomain .contoso.com

# SSL Ports
acl SSL_ports port 443 8180 8443 563 1494 2598 8531

# Standard Ports
acl Safe_ports port 80 # http
acl Safe_ports port 81           # http for Pacific Brokerage
acl Safe_ports port 21 # ftp
acl Safe_ports port 443 563 # http
acl Safe_ports port 70 # gopher
acl Safe_ports port 210 # wais
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 Safe_ports port 8080 8081 8082 8088 8180
acl Safe_ports port 3128         # Squid http server
acl Safe_ports port 1494 2598   # ICA - Citrix
acl Safe_ports port 7000 8000   # Oracle
acl Safe_ports port 9000         # Oracle
acl Safe_ports port 8530 # WSUS
acl Safe_ports port 55905 # WSUS
acl Safe_ports port 1025-65535 # unregistered ports

external_acl_type AD_group %LOGIN c:/squid/libexec/mswin_check_ad_group.exe -G
acl AuthorizedUsers proxy_auth REQUIRED

# ACL - Microsoft
acl msdomains dstdomain .windowsupdate.com 
acl msdomains dstdomain .microsoft.com
acl msdomains dstdomain .windows.com
acl msdomains dstdomain .live.com
acl msdomains dstdomain .msecnd.net
acl msdomains dstdomain .microsoftonline.com
acl msdomains dstdomain .office365.com
acl msdomains dstdomain .lync.com
acl msdomains dstdomain .office.com
acl msdomains dstdomain .onmicrosoft.com
acl msdomains dstdomain .microsoftonline-p.com
acl msdomains dstdomain .microsoftonline-p.net
acl msdomains dstdomain .microsoftonlineimages.com
acl msdomains dstdomain .microsoftonlinesupport.net
acl msdomains dstdomain .msocdn.com
acl msdomains dstdomain .msn.com
acl msdomains dstdomain .msn.co.jp
acl msdomains dstdomain .msn.co.uk
acl msdomains dstdomain .office.net
acl msdomains dstdomain .aadrm.com
acl msdomains dstdomain .cloudapp.net
acl msdomains dstdomain .windowsazure.com
acl msdomains dstdomain .phonefactor.net
acl msdomains dstdomain .symcb.com

# ACL - SSL Providers
acl registars dstdomain .verisign.com
acl registars dstdomain .godaddy.com

# LYNC
acl lync2013 dst 65.54.54.128/25
acl lync2013 dst 65.55.121.128/27
acl lync2013 dst 65.55.127.0/24
acl lync2013 dst 111.221.17.128/27
acl lync2013 dst 111.221.22.64/26
acl lync2013 dst 111.221.76.96/27
acl lync2013 dst 111.221.76.128/25
acl lync2013 dst 111.221.77.0/26
acl lync2013 dst 134.170.0.0/25
acl lync2013 dst 157.55.40.128/25
acl lync2013 dst 157.55.46.0/27
acl lync2013 dst 157.55.46.64/26
acl lync2013 dst 157.55.104.96/27
acl lync2013 dst 157.55.229.128/27
acl lync2013 dst 157.55.232.128/26
acl lync2013 dst 157.55.238.0/25
acl lync2013 dst 207.46.5.0/24
acl lync2013 dst 207.46.7.128/27
acl lync2013 dst 207.46.57.0/25

# OFFICE 365 PORTAL AND IDENTITY
acl 365portal dst 23.96.208.238
acl 365portal dst 23.97.64.252
acl 365portal dst 23.97.68.113
acl 365portal dst 23.97.70.147
acl 365portal dst 23.97.72.158
acl 365portal dst 23.97.72.161
acl 365portal dst 23.97.72.165
acl 365portal dst 23.97.98.128
acl 365portal dst 23.97.99.4
acl 365portal dst 23.97.99.164
acl 365portal dst 23.97.100.76
acl 365portal dst 23.97.100.92
acl 365portal dst 23.97.100.105
acl 365portal dst 23.97.100.152
acl 365portal dst 23.97.102.90
acl 365portal dst 23.97.148.36
acl 365portal dst 23.97.148.228
acl 365portal dst 23.98.66.168
acl 365portal dst 23.98.69.116
acl 365portal dst 23.98.70.90
acl 365portal dst 23.99.129.26
acl 365portal dst 23.99.129.173
acl 365portal dst 23.99.194.77
acl 365portal dst 23.99.196.232
acl 365portal dst 23.99.226.167
acl 365portal dst 23.99.227.124
acl 365portal dst 23.102.64.16
acl 365portal dst 23.102.64.255
acl 365portal dst 23.102.65.171
acl 365portal dst 23.102.65.203
acl 365portal dst 23.102.65.221
acl 365portal dst 65.52.64.61
acl 365portal dst 65.52.64.230
acl 365portal dst 65.52.136.224
acl 365portal dst 65.52.144.125
acl 365portal dst 65.52.148.27
acl 365portal dst 65.52.184.75
acl 365portal dst 65.52.196.64
acl 365portal dst 65.52.228.75
acl 365portal dst 65.52.228.100
acl 365portal dst 65.52.236.160
acl 365portal dst 65.52.244.66
acl 365portal dst 65.54.54.32/27
acl 365portal dst 65.54.55.201
acl 365portal dst 65.54.74.0/23
acl 365portal dst 65.54.80.0/20
acl 365portal dst 65.54.165.0/25
acl 365portal dst 65.55.86.0/23
acl 365portal dst 65.55.233.0/27
acl 365portal dst 65.55.239.168
acl 365portal dst 70.37.56.152
acl 365portal dst 70.37.97.234
acl 365portal dst 70.37.128.0/23
acl 365portal dst 70.37.142.0/23
acl 365portal dst 70.37.150.128/25
acl 365portal dst 70.37.159.0/24
acl 365portal dst 70.37.160.72
acl 365portal dst 70.37.160.202
acl 365portal dst 94.245.68.0/22
acl 365portal dst 94.245.82.0/23
acl 365portal dst 94.245.84.0/24
acl 365portal dst 94.245.86.0/24
acl 365portal dst 94.245.88.223
acl 365portal dst 94.245.88.194
acl 365portal dst 94.245.117.53
acl 365portal dst 94.245.108.85
acl 365portal dst 111.221.16.0/21
acl 365portal dst 111.221.24.0/21
acl 365portal dst 111.221.70.0/25
acl 365portal dst 111.221.71.0/25
acl 365portal dst 111.221.111.196
acl 365portal dst 111.221.127.112/28
acl 365portal dst 132.245.0.0/16
acl 365portal dst 134.170.0.0/16
acl 365portal dst 137.135.47.6
acl 365portal dst 137.135.47.4
acl 365portal dst 137.135.47.28
acl 365portal dst 137.116.32.43
acl 365portal dst 137.116.32.61
acl 365portal dst 137.116.48.66
acl 365portal dst 137.116.48.69
acl 365portal dst 137.116.64.162
acl 365portal dst 137.116.129.62/32
acl 365portal dst 137.117.99.175
acl 365portal dst 137.117.103.21
acl 365portal dst 137.135.41.12/32
acl 365portal dst 137.135.42.195/32
acl 365portal dst 137.135.43.100/32
acl 365portal dst 137.135.44.5/32
acl 365portal dst 137.135.44.73/32
acl 365portal dst 137.135.48.128/32
acl 365portal dst 138.91.17.43
acl 365portal dst 138.91.17.108
acl 365portal dst 138.91.18.52
acl 365portal dst 138.91.2.208
acl 365portal dst 138.91.2.210
acl 365portal dst 138.91.2.212
acl 365portal dst 157.55.45.128/25
acl 365portal dst 157.55.59.128/25
acl 365portal dst 157.55.80.175
acl 365portal dst 157.55.80.182
acl 365portal dst 157.55.84.13/32
acl 365portal dst 157.55.84.19/32
acl 365portal dst 157.55.84.80/32
acl 365portal dst 157.55.84.237/32
acl 365portal dst 157.55.130.0/25
acl 365portal dst 157.55.145.0/25
acl 365portal dst 157.55.155.0/25
acl 365portal dst 157.55.168.18
acl 365portal dst 157.55.176.63
acl 365portal dst 157.55.185.100
acl 365portal dst 157.55.194.46
acl 365portal dst 157.55.208.198
acl 365portal dst 157.55.227.192/26
acl 365portal dst 157.55.252.101
acl 365portal dst 157.56.0.0/16
acl 365portal dst 168.61.33.178/32
acl 365portal dst 168.61.35.252/32
acl 365portal dst 168.61.36.121
acl 365portal dst 168.61.37.63/32
acl 365portal dst 168.61.38.105
acl 365portal dst 168.61.39.14/32
acl 365portal dst 168.61.82.81/32
acl 365portal dst 168.61.83.48/32
acl 365portal dst 168.61.85.180/32
acl 365portal dst 168.61.85.193/32
acl 365portal dst 168.61.144.76
acl 365portal dst 168.61.208.197
acl 365portal dst 168.62.4.28
acl 365portal dst 168.62.11.24
acl 365portal dst 168.62.11.117
acl 365portal dst 168.62.16.112
acl 365portal dst 168.62.16.140
acl 365portal dst 168.62.16.149
acl 365portal dst 168.62.24.104
acl 365portal dst 168.62.24.114
acl 365portal dst 168.62.24.150
acl 365portal dst 168.62.41.25
acl 365portal dst 168.62.42.89
acl 365portal dst 168.62.52.198
acl 365portal dst 168.62.52.203
acl 365portal dst 168.62.60.71
acl 365portal dst 168.62.60.80
acl 365portal dst 168.62.104.146
acl 365portal dst 168.62.176.34
acl 365portal dst 168.62.179.4
acl 365portal dst 168.62.180.151
acl 365portal dst 168.63.16.66/32
acl 365portal dst 168.63.16.112/32
acl 365portal dst 168.63.16.114/32
acl 365portal dst 168.63.16.141
acl 365portal dst 168.63.17.221/32
acl 365portal dst 168.63.25.227
acl 365portal dst 168.63.27.2
acl 365portal dst 168.63.166.200
acl 365portal dst 168.63.165.67
acl 365portal dst 168.63.164.177
acl 365portal dst 168.63.208.73/32
acl 365portal dst 168.63.213.203/32
acl 365portal dst 168.63.214.35/32
acl 365portal dst 168.63.216.117/32
acl 365portal dst 168.63.250.173/32
acl 365portal dst 168.63.252.39/32
acl 365portal dst 168.63.252.71/32
acl 365portal dst 191.232.2.128/25
acl 365portal dst 191.233.32.111
acl 365portal dst 191.233.32.201
acl 365portal dst 191.234.6.0/24
acl 365portal dst 191.235.135.139
acl 365portal dst 191.235.135.222
acl 365portal dst 191.236.192.179
acl 365portal dst 191.237.128.159
acl 365portal dst 191.238.80.160
acl 365portal dst 191.238.81.69
acl 365portal dst 191.238.83.220
acl 365portal dst 207.46.57.128/25
acl 365portal dst 207.46.70.0/24
acl 365portal dst 207.46.73.250
acl 365portal dst 207.46.198.0/25
acl 365portal dst 207.46.206.0/23
acl 365portal dst 207.46.216.54
acl 365portal dst 213.199.128.58
acl 365portal dst 213.199.128.91
acl 365portal dst 213.199.148.0/23
acl 365portal dst 213.199.182.128/25

# OFFICE ONLINE
acl office365 dst 134.170.27.64/26
acl office365 dst 134.170.48.0/26
acl office365 dst 134.170.65.64/26
acl office365 dst 134.170.128.192/26
acl office365 dst 134.170.170.64/26
acl office365 dst 191.232.2.64/26

acl dropbox dstdomain .dropbox.com
acl icloud dstdomain .icloud.com

# Squid Cache
acl PURGE method PURGE

http_access deny manager !localhost
http_access allow PURGE localhost
http_access deny PURGE

# The method ACL type allows you to restrict access based on the request HTTP method, i.e. GET (used for downloading), POST (used for uploading) and CONNECT (used for SSL data transfers)
# It is very important that you stop CONNECT type requests to non-SSL ports. The CONNECT method allows data transfer in any direction at any time, regardless of the transport protocol used.
acl CONNECT method CONNECT
http_access deny CONNECT !SSL_ports

# Deny access to all ports except the ones defined
http_access deny !Safe_ports
# This blocks attempts to request http://localhost on the proxy server via the proxy. 
http_access deny localhost
# Deny caching for everyone so that there is not caching at all
cache deny all

http_access allow msdomains
http_access allow lync2013
http_access allow 365portal
http_access allow office365
http_access allow registars
http_access allow dropbox
http_access allow icloud

http_access allow CONNECT msdomains
http_access allow CONNECT lync2013
http_access allow CONNECT 365portal
http_access allow CONNECT office365
http_access allow CONNECT registars
http_access allow CONNECT dropbox
http_access allow CONNECT icloud

# Deny access to proxy to everyone except Authorized Users group in AD
http_access deny !AuthorizedUsers

# Disable caching
always_direct allow msdomains all
always_direct allow registars all
always_direct allow lync2013 all
always_direct allow 365portal all
always_direct allow office365 all

# Allow direct connection if the destination machine is on LAN
always_direct allow lan_dst
# Allow http access from machines on LAN
http_access allow lan_src
# Default deny
http_access deny all
http_reply_access allow all
icp_access allow all

# Squid should not check with neighbours'/parents' cache and should go to target web-server.
hierarchy_stoplist cgi-bin ?

# Logging
cache_dir ufs c:/squid/var/cache 100 16 256
access_log c:/squid/var/logs/access.log squid
cache_log c:/squid/var/logs/cache.log
cache_store_log none
logfile_rotate 4
log_ip_on_direct on
debug_options ALL,1
log_fqdn off

# SquidGuard
redirect_program c:/squidguard/squidguard.exe -c c:/squidguard/conf/squidguard.conf
redirect_children 5

# Caching
cache_mgr ittechs@xxxxxxxx
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

# Dont cache these pages
acl DYNAMIC_CONTENT urlpath_regex cgi-bin \.cgi \.pl \.php3 \.asp \.php
no_cache deny DYNAMIC_CONTENT 

# Other stuff?
acl shoutcast rep_header X-HTTP09-First-Line ^ICY.[0-9]
upgrade_http0.9 deny shoutcast
acl apache rep_header Server ^Apache
broken_vary_encoding allow apache
error_directory c:/squid/share/errors/English

# Various features turned off.
snmp_port 0
icp_port 0
htcp_port 0

coredump_dir c:/squid/var/cache
pid_filename c:/squid/var/squid.pid
mime_table c:/squid/etc/mime.conf
unlinkd_program c:/squid/libexec/unlinkd.exe

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