Hi all again, Thanks for your patience and help. A few more improvements yet I'm still stuck :( This is /etc/freeradius/sites-default/inner-tunnel: (the section post_auth) if (Ldap-Group == "SeminaryAdmin") { update reply { Tunnel-Type := "VLAN", Tunnel-Medium-Type := "802", Tunnel-Private-Group-ID := "12" } } I tried Ldap-Group == SeminaryAdmin / "SeminaryAdmin" / "cn=SeminaryAdmin,ou=SeminaryOU,dc=seminary,dc=local" but neither of the 3 options worked. Can you please suggest further, this is really mind boggling!! :( This is the debug log: Fri Aug 19 11:01:56 2016 : Info: # Executing section authorize from file /etc/freeradius/sites-enabled/default Fri Aug 19 11:01:56 2016 : Info: +group authorize { Fri Aug 19 11:01:56 2016 : Info: ++[preprocess] = ok Fri Aug 19 11:01:56 2016 : Info: ++[chap] = noop Fri Aug 19 11:01:56 2016 : Info: ++[mschap] = noop Fri Aug 19 11:01:56 2016 : Info: ++[digest] = noop Fri Aug 19 11:01:56 2016 : Info: [suffix] No '@' in User-Name = "ttester", looking up realm NULL Fri Aug 19 11:01:56 2016 : Info: [suffix] No such realm "NULL" Fri Aug 19 11:01:56 2016 : Info: ++[suffix] = noop Fri Aug 19 11:01:56 2016 : Info: [eap] No EAP-Message, not doing EAP Fri Aug 19 11:01:56 2016 : Info: ++[eap] = noop Fri Aug 19 11:01:56 2016 : Info: ++[files] = noop Fri Aug 19 11:01:56 2016 : Info: [ldap] performing user authorization for ttester Fri Aug 19 11:01:56 2016 : Info: [ldap] expand: %{Stripped-User-Name} -> Fri Aug 19 11:01:56 2016 : Info: [ldap] ... expanding second conditional Fri Aug 19 11:01:56 2016 : Info: [ldap] expand: %{User-Name} -> ttester Fri Aug 19 11:01:56 2016 : Info: [ldap] expand: (uid=%{%{Stripped-User-Name}:-%{User-Name}}) -> (uid=ttester) Fri Aug 19 11:01:56 2016 : Info: [ldap] expand: ou=SeminaryOU,dc=seminary,dc=local -> ou=SeminaryOU,dc=seminary,dc=local Fri Aug 19 11:01:56 2016 : Debug: [ldap] ldap_get_conn: Checking Id: 0 Fri Aug 19 11:01:56 2016 : Debug: [ldap] ldap_get_conn: Got Id: 0 Fri Aug 19 11:01:56 2016 : Debug: [ldap] attempting LDAP reconnection Fri Aug 19 11:01:56 2016 : Debug: [ldap] (re)connect to seminary.local:389, authentication 0 Fri Aug 19 11:01:56 2016 : Debug: [ldap] bind as cn=admin,dc=seminary,dc=local/S3m1n4ry to seminary.local:389 Fri Aug 19 11:01:56 2016 : Debug: [ldap] waiting for bind result ... Fri Aug 19 11:01:56 2016 : Debug: [ldap] Bind was successful Fri Aug 19 11:01:56 2016 : Debug: [ldap] performing search in ou=SeminaryOU,dc=seminary,dc=local, with filter (uid=ttester) Fri Aug 19 11:01:56 2016 : Info: [ldap] No default NMAS login sequence Fri Aug 19 11:01:56 2016 : Info: [ldap] looking for check items in directory... Fri Aug 19 11:01:56 2016 : Debug: [ldap] userPassword -> Password-With-Header == "{SSHA}T4sU9zSLN/Auop+ImthH4nLyLG/rPU0R" Fri Aug 19 11:01:56 2016 : Info: [ldap] looking for reply items in directory... Fri Aug 19 11:01:56 2016 : Debug: [ldap] ldap_release_conn: Release Id: 0 Fri Aug 19 11:01:56 2016 : Info: ++[ldap] = ok Fri Aug 19 11:01:56 2016 : Info: ++[expiration] = noop Fri Aug 19 11:01:56 2016 : Info: ++[logintime] = noop Fri Aug 19 11:01:56 2016 : Info: ++[pap] = updated Fri Aug 19 11:01:56 2016 : Info: +} # group authorize = updated Fri Aug 19 11:01:56 2016 : Info: Found Auth-Type = PAP Fri Aug 19 11:01:56 2016 : Info: # Executing group from file /etc/freeradius/sites-enabled/default Fri Aug 19 11:01:56 2016 : Info: +group PAP { Fri Aug 19 11:01:56 2016 : Info: [pap] login attempt with password "openldap" Fri Aug 19 11:01:56 2016 : Info: [pap] Using SSHA encryption. Fri Aug 19 11:01:56 2016 : Info: [pap] Normalizing SSHA1-Password from base64 encoding Fri Aug 19 11:01:56 2016 : Info: [pap] User authenticated successfully Fri Aug 19 11:01:56 2016 : Info: ++[pap] = ok Fri Aug 19 11:01:56 2016 : Info: +} # group PAP = ok Fri Aug 19 11:01:56 2016 : Info: # Executing section post-auth from file /etc/freeradius/sites-enabled/default Fri Aug 19 11:01:56 2016 : Info: +group post-auth { Fri Aug 19 11:01:56 2016 : Info: ++? if (Ldap-Group == SeminaryAdmin) Fri Aug 19 11:01:56 2016 : Debug: [ldap] Entering ldap_groupcmp() Fri Aug 19 11:01:56 2016 : Info: expand: ou=SeminaryOU,dc=seminary,dc=local -> ou=SeminaryOU,dc=seminary,dc=local Fri Aug 19 11:01:56 2016 : Info: expand: (|(&(objectClass=GroupOfNames)(member=%{control:Ldap-UserDn}))(&(objectClass=GroupOfUniqueNames)(uniquemember=%{control:Ldap-UserDn}))) -> (|(&(objectClass=GroupOfNames)(member=cn\3dttester\2ccn\3dSeminaryAdmin\2cou\3dSeminaryOU\2cdc\3dseminary\2cdc\3dlocal))(&(objectClass=GroupOfUniqueNames)(uniquemember=cn\3dttester\2ccn\3dSeminaryAdmin\2cou\3dSeminaryOU\2cdc\3dseminary\2cdc\3dlocal))) Fri Aug 19 11:01:56 2016 : Debug: [ldap] ldap_get_conn: Checking Id: 0 Fri Aug 19 11:01:56 2016 : Debug: [ldap] ldap_get_conn: Got Id: 0 Fri Aug 19 11:01:56 2016 : Debug: [ldap] performing search in ou=SeminaryOU,dc=seminary,dc=local, with filter (&(cn=SeminaryAdmin)(|(&(objectClass=GroupOfNames)(member=cn\3dttester\2ccn\3dSeminaryAdmin\2cou\3dSeminaryOU\2cdc\3dseminary\2cdc\3dlocal))(&(objectClass=GroupOfUniqueNames)(uniquemember=cn\3dttester\2ccn\3dSeminaryAdmin\2cou\3dSeminaryOU\2cdc\3dseminary\2cdc\3dlocal)))) Fri Aug 19 11:01:56 2016 : Debug: [ldap] object not found Fri Aug 19 11:01:56 2016 : Debug: [ldap] ldap_release_conn: Release Id: 0 Fri Aug 19 11:01:56 2016 : Debug: rlm_ldap::ldap_groupcmp: Group SeminaryAdmin not found or user is not a member. Fri Aug 19 11:01:56 2016 : Info: ? Evaluating (Ldap-Group == SeminaryAdmin) -> FALSE Fri Aug 19 11:01:56 2016 : Info: ++? if (Ldap-Group == SeminaryAdmin) -> FALSE Fri Aug 19 11:01:56 2016 : Info: ++else else { Fri Aug 19 11:01:56 2016 : Info: +++[reject] = reject Fri Aug 19 11:01:56 2016 : Info: ++} # else else = reject Fri Aug 19 11:01:56 2016 : Info: +} # group post-auth = reject Fri Aug 19 11:01:56 2016 : Info: Using Post-Auth-Type Reject Fri Aug 19 11:01:56 2016 : Info: # Executing group from file /etc/freeradius/sites-enabled/default Fri Aug 19 11:01:56 2016 : Info: +group REJECT { Fri Aug 19 11:01:56 2016 : Info: [eap] Request didn't contain an EAP-Message, not inserting EAP-Failure Fri Aug 19 11:01:56 2016 : Info: ++[eap] = noop Fri Aug 19 11:01:56 2016 : Info: [attr_filter.access_reject] expand: %{User-Name} -> ttester Fri Aug 19 11:01:56 2016 : Debug: attr_filter: Matched entry DEFAULT at line 11 Fri Aug 19 11:01:56 2016 : Info: ++[attr_filter.access_reject] = updated Fri Aug 19 11:01:56 2016 : Info: +} # group REJECT = updated Fri Aug 19 11:01:56 2016 : Info: Delaying reject of request 0 for 1 seconds Fri Aug 19 11:01:56 2016 : Debug: Going to the next request Fri Aug 19 11:01:56 2016 : Debug: Waking up in 0.9 seconds. Fri Aug 19 11:01:57 2016 : Info: Sending delayed reject for request 0 Sending Access-Reject of id 4 to 127.0.0.1 port 49728 Fri Aug 19 11:01:57 2016 : Debug: Waking up in 4.9 seconds. Fri Aug 19 11:02:02 2016 : Info: Cleaning up request 0 ID 4 with timestamp +3 Fri Aug 19 11:02:02 2016 : Info: Ready to process requests.