We have successfully deployed a squid3 proxy in a Windows AD domain that authenticates users with the kerberos helper and uses LDAP queries to allow access based on Security groups in AD. This works perfectly for IE, FF and Chrome and no authentication pop-ups occur. We realised that not all applications use this authentication and that sometimes non-domain PC's might need internet access so LDAP was to be used as a backup authentication method. I tested using a non-domain user on a Win7 workstation and when opening IE it prompts for a login as I had expected but I notice that I have to input the username and password a second time before it will allow access. I also notice when this happens that the second authentication dialogue automatically adds the domain prefix, i.e. DOMAIN\user and the password is already entered. Looking at the logs it seems as though this second attempt is in fact the kerberos auth not LDAP as I had initially thought, this is what's logged in /var/cache/squid3/cache.log whilst this takes place (long lines have been truncated). 2011/12/23 10:25:13| squid_kerb_auth: DEBUG: Got 'YR TlRMTVNTUAABAAAAl4II4gAAAAAAAAAAAAAAAAAAAAAGAbAdAAAADw==' from squid (length: 59). 2011/12/23 10:25:13| squid_kerb_auth: DEBUG: Decode 'TlRMTVNTUAABAAAAl4II4gAAAAAAAAAAAAAAAAAAAAAGAbAdAAAADw==' (decoded length: 40). 2011/12/23 10:25:13| squid_kerb_auth: WARNING: received type 1 NTLM token 2011/12/23 10:25:13| authenticateNegotiateHandleReply: Error validating user via Negotiate. Error returned 'BH received type 1 NTLM token' 2011/12/23 10:25:13| squid_kerb_auth: DEBUG: Got 'YR TlRMTVNTUAABAAAAl4II4gAAAAAAAAAAAAAAAAAAAAAGAbAdAAAADw==' from squid (length: 59). 2011/12/23 10:25:13| squid_kerb_auth: DEBUG: Decode 'TlRMTVNTUAABAAAAl4II4gAAAAAAAAAAAAAAAAAAAAAGAbAdAAAADw==' (decoded length: 40). 2011/12/23 10:25:13| squid_kerb_auth: WARNING: received type 1 NTLM token 2011/12/23 10:25:13| authenticateNegotiateHandleReply: Error validating user via Negotiate. Error returned 'BH received type 1 NTLM token' 2011/12/23 10:25:14| squid_kerb_auth: DEBUG: Got 'YR TlRMTVNTUAABAAAAl4II4gAAAAAAAAAAAAAAAAAAAAAGAbAdAAAADw==' from squid (length: 59). 2011/12/23 10:25:14| squid_kerb_auth: DEBUG: Decode 'TlRMTVNTUAABAAAAl4II4gAAAAAAAAAAAAAAAAAAAAAGAbAdAAAADw==' (decoded length: 40). 2011/12/23 10:25:14| squid_kerb_auth: WARNING: received type 1 NTLM token 2011/12/23 10:25:14| authenticateNegotiateHandleReply: Error validating user via Negotiate. Error returned 'BH received type 1 NTLM token' 2011/12/23 10:25:14| squid_kerb_auth: DEBUG: Got 'YR TlRMTVNTUAABAAAAl4II4gAAAAAAAAAAAAAAAAAAAAAGAbAdAAAADw==' from squid (length: 59). 2011/12/23 10:25:14| squid_kerb_auth: DEBUG: Decode 'TlRMTVNTUAABAAAAl4II4gAAAAAAAAAAAAAAAAAAAAAGAbAdAAAADw==' (decoded length: 40). 2011/12/23 10:25:14| squid_kerb_auth: WARNING: received type 1 NTLM token 2011/12/23 10:25:14| authenticateNegotiateHandleReply: Error validating user via Negotiate. Error returned 'BH received type 1 NTLM token' 2011/12/23 10:26:12| squid_kerb_auth: DEBUG: Got 'YR TlRMTVNTUAABAAAAl4II4gAAAAAAAAAAAAAAAAAAAAAGAbAdAAAADw==' from squid (length: 59). 2011/12/23 10:26:12| squid_kerb_auth: DEBUG: Decode 'TlRMTVNTUAABAAAAl4II4gAAAAAAAAAAAAAAAAAAAAAGAbAdAAAADw==' (decoded length: 40). 2011/12/23 10:26:12| squid_kerb_auth: WARNING: received type 1 NTLM token 2011/12/23 10:26:12| authenticateNegotiateHandleReply: Error validating user via Negotiate. Error returned 'BH received type 1 NTLM token' 2011/12/23 10:27:11| squid_kerb_auth: DEBUG: Got 'YR YIIGmQYGKwYBBQUCoIIGjTCC [...Truncated...] h07dexafHYw==' from squid (length: 2263). 2011/12/23 10:27:11| squid_kerb_auth: DEBUG: Decode 'YIIGmQ [...Truncated...] /h07dexafHYw==' (decoded length: 1693). 2011/12/23 10:27:11| squid_kerb_auth: DEBUG: AF oYG2MIG [...Truncated...] jJkPFv+8= username@EXAMPLE.LOCAL Besides that we also have a problem with iTunes access. When iTunes runs it prompts for authentication regardless of whether the user is logged in to the domain or not and fails to authenticate regardless of entering the login multiple times. The following is logged in /var/log/squid3/cache.log. 2011/12/23 10:03:13| squid_kerb_auth: DEBUG: Got 'YR TlRMTVNTUAABAAAAl4II4gAAAAAAAAAAAAAAAAAAAAAGAbAdAAAADw==' from squid (length: 59). 2011/12/23 10:03:13| squid_kerb_auth: DEBUG: Decode 'TlRMTVNTUAABAAAAl4II4gAAAAAAAAAAAAAAAAAAAAAGAbAdAAAADw==' (decoded length: 40). 2011/12/23 10:03:13| squid_kerb_auth: WARNING: received type 1 NTLM token 2011/12/23 10:03:13| authenticateNegotiateHandleReply: Error validating user via Negotiate. Error returned 'BH received type 1 NTLM token' The squid.conf is listed below. Am I mistaken about the authentication failing over to LDAP if kerberos fails - if so, is there a way to make this work for computers/software that cannot do kerberos besides white listing domains?? I'm also a bit unsure about my http_access lines, hence you will see some commented out from some testing I am doing. ### /etc/squid3/squid.conf Configuration File ####### ### cache manager cache_mgr cacheadmin@xxxxxxxxxxx ### kerberos authentication auth_param negotiate program /usr/lib/squid3/squid_kerb_auth -d -s HTTP/squidproxy.example.local auth_param negotiate children 10 auth_param negotiate keep_alive on ### provide access via ldap for clients not authenticated via kerberos auth_param basic program /usr/lib/squid3/squid_ldap_auth -R \ -b "dc=example,dc=local" \ -D squid@example.local \ -W /etc/squid3/ldappass.txt \ -f sAMAccountName=%s \ -h domaincontroller.example.local auth_param basic children 10 auth_param basic realm Internet Proxy auth_param basic credentialsttl 1 minute ### ldap authorizations # Internet Users Blocked external_acl_type internet_users_blocked %LOGIN /usr/lib/squid3/squid_ldap_group -R -K \ -b "dc=example,dc=local" \ -D squid@example.local \ -W /etc/squid3/ldappass.txt \ -f "(&(objectclass=person)(sAMAccountName=%v)(memberof=cn=Internet Users Blocked,ou=Security Groups,ou=MyBusiness,dc=example,dc=local))" \ -h domaincontroller.example.local # Internet Users Restricted external_acl_type internet_users_restricted %LOGIN /usr/lib/squid3/squid_ldap_group -R -K \ -b "dc=example,dc=local" \ -D squid@example.local \ -W /etc/squid3/ldappass.txt \ -f "(&(objectclass=person)(sAMAccountName=%v)(memberof=cn=Internet Users Restricted,ou=Security Groups,ou=MyBusiness,dc=example,dc=local))" \ -h domaincontroller.example.local # Internet Users Standard external_acl_type internet_users_standard %LOGIN /usr/lib/squid3/squid_ldap_group -R -K \ -b "dc=example,dc=local" \ -D squid@example.local \ -W /etc/squid3/ldappass.txt \ -f "(&(objectclass=person)(sAMAccountName=%v)(memberof=cn=Internet Users Standard,ou=Security Groups,ou=MyBusiness,dc=example,dc=local))" \ -h domaincontroller.example.local # Internet Users Full NoLog external_acl_type internet_users_full_nolog %LOGIN /usr/lib/squid3/squid_ldap_group -R -K \ -b "dc=example,dc=local" \ -D squid@example.local \ -W /etc/squid3/ldappass.txt \ -f "(&(objectclass=person)(sAMAccountName=%v)(memberof=cn=Internet Users Full NoLog,ou=Security Groups,ou=MyBusiness,dc=example,dc=local))" \ -h domaincontroller.example.local # Internet Users Full Log external_acl_type internet_users_full_log %LOGIN /usr/lib/squid3/squid_ldap_group -R -K \ -b "dc=example,dc=local" \ -D squid@example.local \ -W /etc/squid3/ldappass.txt \ -f "(&(objectclass=person)(sAMAccountName=%v)(memberof=cn=Internet Users Full Log,ou=Security Groups,ou=MyBusiness,dc=example,dc=local))" \ -h domaincontroller.example.local ### acl for proxy auth and ldap authorizations acl auth proxy_auth REQUIRED # format "acl, aclname, acltype, acltypename, activedirectorygroup" acl BlockedAccessLog external internet_users_blocked Internet\ Users\ Blocked acl RestrictedAccessLog external internet_users_restricted Internet\ Users\ Restricted acl StandardAccessLog external internet_users_standard Internet\ Users\ Standard acl FullAccessLog external internet_users_full_log Internet\ Users\ Full\ Log acl FullAccessNoLog external internet_users_full_nolog Internet\ Users\ Full\ NoLog acl whitelistsites url_regex -i "/etc/squid3/whitelistsites.txt" acl blockedsites url_regex -i "/etc/squid3/blockedsites.txt" ### squid defaults acl manager proto cache_object acl localhost src 127.0.0.1/32 ::1 acl to_localhost dst 127.0.0.0/8 0.0.0.0/32 ::1 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 CONNECT method CONNECT http_access allow manager localhost http_access deny manager http_access deny !Safe_ports http_access deny CONNECT !SSL_ports http_access allow localhost ### enforce auth: order of rules is important for authorization levels no_cache deny whitelistsites #http_access deny !auth # users in BlockedAccessLog are deny all #http_access deny BlockedAccessLog all http_access allow whitelistsites #http_access deny RestrictedAccessLog all http_access allow FullAccessNoLog auth http_access allow FullAccessLog auth http_access deny blockedsites http_access allow StandardAccessLog auth ### logging # don't log whitelistsites, FullAccessNoLog access_log /var/log/squid3/access.log squid !whitelistsites !FullAccessNoLog ### squid defaults http_access deny all http_port 3128 hierarchy_stoplist cgi-bin ? coredump_dir /var/spool/squid3 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 Thanks and Merry Christmas! James.