Ok I have been trying various configurations in my squid.conf, I am sure that I was over complicating the issue. Here is a stripped down version that I would like to use basic if NTLM fails, but it never drops down to the basic authentication. I think that I am putting probably alot more in this than I need to get my point across, but if I log into a machine locally, an try to get to the Internet it prompts me, but doesn't seem to have the realm correct or use the basic authentication, we have multiple domains and when we use auth_param basic program /opt/samba/bin/ntlm_auth --helper-protocol=squid-2.5-basic users have to know there domain, and some of our users aren't that bright: cache_peer firewall.domain.com parent 8080 0 no-query default emulate_httpd_log on auth_param ntlm program /usr/bin/ntlm_auth --helper-protocol=squid-2.5-ntlmssp --require-membership-of={SID of our Internet Group} auth_param ntlm children 5 #auth_param basic program /opt/samba/bin/ntlm_auth --helper-protocol=squid-2.5-basic auth_param basic program /opt/squid/libexec/squid_ldap_auth -R -b "DC=domain,DC=com" -D "cn=Squid,OU=Service Accounts,DC=hdq,DC=domain,DC=com" -w "xxxxxx" -f sAMAccountName=%s -h directory.hdq.domain.com -p 3268 auth_param basic children 5 auth_param basic realm Squid proxy-caching web server auth_param basic credentialsttl 2 hours acl all src 0.0.0.0/0.0.0.0 acl authenticated_users proxy_auth REQUIRED never_direct allow all http_access allow authenticated_users http_access deny all http_reply_access allow all icp_access allow all