I am running into an issue with connecting to Google LDAP service (1), oddly enough if I change it from ldaps://ldap.google.com:636 to just ldap://ldap.xxxxxxxxxx it will “connect” but it will change the port to 389. (2) When its on the ldap version it will run but says it fails - ldap: ERROR: Failed performing search: Confidentiality required (1) rlm_ldap (ldap): Opening additional connection (0), 1 of 32 pending slots used rlm_ldap (ldap): Connecting to ldaps://ldap.google.com:636 TLS: can't connect: (unknown error code). rlm_ldap (ldap): Bind with admin@foundationacademy.net to ldaps://ldap.google.com:636 failed: Can't contact LDAP server rlm_ldap (ldap): Opening connection failed (0) rlm_ldap (ldap): Removing connection pool /etc/freeradius/3.0/mods-enabled/ldap[8]: Instantiation failed for module "ldap" (2) rlm_ldap (ldap): Opening additional connection (5), 1 of 27 pending slots used rlm_ldap (ldap): Connecting to ldap://ldap.google.com:389 rlm_ldap (ldap): Waiting for bind result... rlm_ldap (ldap): Bind successful (0) [ldap] = fail (0) } # authorize = fail (0) Invalid user (ldap: Failed performing search: Confidentiality required): I have included the full code below. (1) root@FreeRadius:~# freeradius -X FreeRADIUS Version 3.0.20 Copyright (C) 1999-2019 The FreeRADIUS server project and contributors There is NO warranty; not even for MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE You may redistribute copies of FreeRADIUS under the terms of the GNU General Public License For more information about these matters, see the file named COPYRIGHT Starting - reading configuration files ... including dictionary file /usr/share/freeradius/dictionary including dictionary file /usr/share/freeradius/dictionary.dhcp including dictionary file /usr/share/freeradius/dictionary.vqp including dictionary file /etc/freeradius/3.0/dictionary including configuration file /etc/freeradius/3.0/radiusd.conf including configuration file /etc/freeradius/3.0/proxy.conf including configuration file /etc/freeradius/3.0/clients.conf including files in directory /etc/freeradius/3.0/mods-enabled/ including configuration file /etc/freeradius/3.0/mods-enabled/dynamic_clients including configuration file /etc/freeradius/3.0/mods-enabled/replicate including configuration file /etc/freeradius/3.0/mods-enabled/detail including configuration file /etc/freeradius/3.0/mods-enabled/ldap including configuration file /etc/freeradius/3.0/mods-enabled/echo including configuration file /etc/freeradius/3.0/mods-enabled/mschap including configuration file /etc/freeradius/3.0/mods-enabled/unpack including configuration file /etc/freeradius/3.0/mods-enabled/exec including configuration file /etc/freeradius/3.0/mods-enabled/realm including configuration file /etc/freeradius/3.0/mods-enabled/soh including configuration file /etc/freeradius/3.0/mods-enabled/chap including configuration file /etc/freeradius/3.0/mods-enabled/pap including configuration file /etc/freeradius/3.0/mods-enabled/radutmp including configuration file /etc/freeradius/3.0/mods-enabled/logintime including configuration file /etc/freeradius/3.0/mods-enabled/cache_eap including configuration file /etc/freeradius/3.0/mods-enabled/attr_filter including configuration file /etc/freeradius/3.0/mods-enabled/sradutmp including configuration file /etc/freeradius/3.0/mods-enabled/preprocess including configuration file /etc/freeradius/3.0/mods-enabled/utf8 including configuration file /etc/freeradius/3.0/mods-enabled/expiration including configuration file /etc/freeradius/3.0/mods-enabled/passwd including configuration file /etc/freeradius/3.0/mods-enabled/digest including configuration file /etc/freeradius/3.0/mods-enabled/linelog including configuration file /etc/freeradius/3.0/mods-enabled/ntlm_auth including configuration file /etc/freeradius/3.0/mods-enabled/unix including configuration file /etc/freeradius/3.0/mods-enabled/always including configuration file /etc/freeradius/3.0/mods-enabled/detail.log including configuration file /etc/freeradius/3.0/mods-enabled/eap including configuration file /etc/freeradius/3.0/mods-enabled/expr including configuration file /etc/freeradius/3.0/mods-enabled/files including files in directory /etc/freeradius/3.0/policy.d/ including configuration file /etc/freeradius/3.0/policy.d/filter including configuration file /etc/freeradius/3.0/policy.d/dhcp including configuration file /etc/freeradius/3.0/policy.d/debug including configuration file /etc/freeradius/3.0/policy.d/accounting including configuration file /etc/freeradius/3.0/policy.d/cui including configuration file /etc/freeradius/3.0/policy.d/control including configuration file /etc/freeradius/3.0/policy.d/abfab-tr including configuration file /etc/freeradius/3.0/policy.d/moonshot-targeted-ids including configuration file /etc/freeradius/3.0/policy.d/canonicalization including configuration file /etc/freeradius/3.0/policy.d/operator-name including configuration file /etc/freeradius/3.0/policy.d/eap including configuration file /etc/freeradius/3.0/policy.d/rfc7542 including files in directory /etc/freeradius/3.0/sites-enabled/ including configuration file /etc/freeradius/3.0/sites-enabled/inner-tunnel including configuration file /etc/freeradius/3.0/sites-enabled/default main { security { user = "freerad" group = "freerad" allow_core_dumps = no } name = "freeradius" prefix = "/usr" localstatedir = "/var" logdir = "/var/log/freeradius" run_dir = "/var/run/freeradius" } main { name = "freeradius" prefix = "/usr" localstatedir = "/var" sbindir = "/usr/sbin" logdir = "/var/log/freeradius" run_dir = "/var/run/freeradius" libdir = "/usr/lib/freeradius" radacctdir = "/var/log/freeradius/radacct" hostname_lookups = no max_request_time = 30 cleanup_delay = 5 max_requests = 16384 pidfile = "/var/run/freeradius/freeradius.pid" checkrad = "/usr/sbin/checkrad" debug_level = 0 proxy_requests = yes log { stripped_names = no auth = no auth_badpass = no auth_goodpass = no colourise = yes msg_denied = "You are already logged in - access denied" } resources { } security { max_attributes = 200 reject_delay = 1.000000 status_server = yes } } radiusd: #### Loading Realms and Home Servers #### proxy server { retry_delay = 5 retry_count = 3 default_fallback = no dead_time = 120 wake_all_if_all_dead = no } home_server localhost { ipaddr = 127.0.0.1 port = 1812 type = "auth" secret = <<< secret >>> response_window = 20.000000 response_timeouts = 1 max_outstanding = 65536 zombie_period = 40 status_check = "status-server" ping_interval = 30 check_interval = 30 check_timeout = 4 num_answers_to_alive = 3 revive_interval = 120 limit { max_connections = 16 max_requests = 0 lifetime = 0 idle_timeout = 0 } coa { irt = 2 mrt = 16 mrc = 5 mrd = 30 } } home_server_pool my_auth_failover { type = fail-over home_server = localhost } realm foundationacademy.net { auth_pool = my_auth_failover } realm LOCAL { } radiusd: #### Loading Clients #### client localhost { ipaddr = 172.16.13.29 require_message_authenticator = no secret = <<< secret >>> nas_type = "other" proto = "*" limit { max_connections = 16 lifetime = 0 idle_timeout = 30 } } client localhost_ipv6 { ipv6addr = ::1 require_message_authenticator = no secret = <<< secret >>> limit { max_connections = 16 lifetime = 0 idle_timeout = 30 } } Debugger not attached systemd watchdog is disabled # Creating Auth-Type = mschap # Creating Auth-Type = ldap # Creating Auth-Type = eap # Creating Auth-Type = PAP # Creating Auth-Type = CHAP # Creating Auth-Type = MS-CHAP # Creating Auth-Type = digest radiusd: #### Instantiating modules #### modules { # Loaded module rlm_dynamic_clients # Loading module "dynamic_clients" from file /etc/freeradius/3.0/mods-enabled/dynamic_clients # Loaded module rlm_replicate # Loading module "replicate" from file /etc/freeradius/3.0/mods-enabled/replicate # Loaded module rlm_detail # Loading module "detail" from file /etc/freeradius/3.0/mods-enabled/detail detail { filename = "/var/log/freeradius/radacct/%{%{Packet-Src-IP-Address}:-%{Packet-Src-IPv6-Address}}/detail-%Y%m%d" header = "%t" permissions = 384 locking = no escape_filenames = no log_packet_header = no } # Loaded module rlm_ldap # Loading module "ldap" from file /etc/freeradius/3.0/mods-enabled/ldap ldap { server = "ldaps://ldap.google.com" identity = "admin@foundationacademy.net" password = <<< secret >>> sasl { } user_dn = "LDAP-UserDn" user { scope = "sub" access_positive = yes sasl { } } group { filter = "(objectClass=posixGroup)" scope = "sub" name_attribute = "cn" membership_attribute = "memberOf" cacheable_name = no cacheable_dn = no allow_dangling_group_ref = no } client { filter = "(objectClass=radiusClient)" scope = "sub" base_dn = "dc=foundationacademy,dc=net" } profile { } options { ldap_debug = 40 chase_referrals = yes rebind = yes net_timeout = 1 res_timeout = 10 srv_timelimit = 3 idle = 60 probes = 3 interval = 3 } tls { start_tls = no } } Creating attribute LDAP-Group # Loaded module rlm_exec # Loading module "echo" from file /etc/freeradius/3.0/mods-enabled/echo exec echo { wait = yes program = "/bin/echo %{User-Name}" input_pairs = "request" output_pairs = "reply" shell_escape = yes } # Loaded module rlm_mschap # Loading module "mschap" from file /etc/freeradius/3.0/mods-enabled/mschap mschap { use_mppe = yes require_encryption = no require_strong = no with_ntdomain_hack = yes passchange { } allow_retry = yes winbind_retry_with_normalised_username = no } # Loaded module rlm_unpack # Loading module "unpack" from file /etc/freeradius/3.0/mods-enabled/unpack # Loading module "exec" from file /etc/freeradius/3.0/mods-enabled/exec exec { wait = no input_pairs = "request" shell_escape = yes timeout = 10 } # Loaded module rlm_realm # Loading module "IPASS" from file /etc/freeradius/3.0/mods-enabled/realm realm IPASS { format = "prefix" delimiter = "/" ignore_default = no ignore_null = no } # Loading module "suffix" from file /etc/freeradius/3.0/mods-enabled/realm realm suffix { format = "suffix" delimiter = "@" ignore_default = no ignore_null = no } # Loading module "bangpath" from file /etc/freeradius/3.0/mods-enabled/realm realm bangpath { format = "prefix" delimiter = "!" ignore_default = no ignore_null = no } # Loading module "realmpercent" from file /etc/freeradius/3.0/mods-enabled/realm realm realmpercent { format = "suffix" delimiter = "%" ignore_default = no ignore_null = no } # Loading module "ntdomain" from file /etc/freeradius/3.0/mods-enabled/realm realm ntdomain { format = "prefix" delimiter = "\\" ignore_default = no ignore_null = no } # Loaded module rlm_soh # Loading module "soh" from file /etc/freeradius/3.0/mods-enabled/soh soh { dhcp = yes } # Loaded module rlm_chap # Loading module "chap" from file /etc/freeradius/3.0/mods-enabled/chap # Loaded module rlm_pap # Loading module "pap" from file /etc/freeradius/3.0/mods-enabled/pap pap { normalise = yes } # Loaded module rlm_radutmp # Loading module "radutmp" from file /etc/freeradius/3.0/mods-enabled/radutmp radutmp { filename = "/var/log/freeradius/radutmp" username = "%{User-Name}" case_sensitive = yes check_with_nas = yes permissions = 384 caller_id = yes } # Loaded module rlm_logintime # Loading module "logintime" from file /etc/freeradius/3.0/mods-enabled/logintime logintime { minimum_timeout = 60 } # Loaded module rlm_cache # Loading module "cache_eap" from file /etc/freeradius/3.0/mods-enabled/cache_eap cache cache_eap { driver = "rlm_cache_rbtree" key = "%{%{control:State}:-%{%{reply:State}:-%{State}}}" ttl = 15 max_entries = 0 epoch = 0 add_stats = no } # Loaded module rlm_attr_filter # Loading module "attr_filter.post-proxy" from file /etc/freeradius/3.0/mods-enabled/attr_filter attr_filter attr_filter.post-proxy { filename = "/etc/freeradius/3.0/mods-config/attr_filter/post-proxy" key = "%{Realm}" relaxed = no } # Loading module "attr_filter.pre-proxy" from file /etc/freeradius/3.0/mods-enabled/attr_filter attr_filter attr_filter.pre-proxy { filename = "/etc/freeradius/3.0/mods-config/attr_filter/pre-proxy" key = "%{Realm}" relaxed = no } # Loading module "attr_filter.access_reject" from file /etc/freeradius/3.0/mods-enabled/attr_filter attr_filter attr_filter.access_reject { filename = "/etc/freeradius/3.0/mods-config/attr_filter/access_reject" key = "%{User-Name}" relaxed = no } # Loading module "attr_filter.access_challenge" from file /etc/freeradius/3.0/mods-enabled/attr_filter attr_filter attr_filter.access_challenge { filename = "/etc/freeradius/3.0/mods-config/attr_filter/access_challenge" key = "%{User-Name}" relaxed = no } # Loading module "attr_filter.accounting_response" from file /etc/freeradius/3.0/mods-enabled/attr_filter attr_filter attr_filter.accounting_response { filename = "/etc/freeradius/3.0/mods-config/attr_filter/accounting_response" key = "%{User-Name}" relaxed = no } # Loading module "sradutmp" from file /etc/freeradius/3.0/mods-enabled/sradutmp radutmp sradutmp { filename = "/var/log/freeradius/sradutmp" username = "%{User-Name}" case_sensitive = yes check_with_nas = yes permissions = 420 caller_id = no } # Loaded module rlm_preprocess # Loading module "preprocess" from file /etc/freeradius/3.0/mods-enabled/preprocess preprocess { huntgroups = "/etc/freeradius/3.0/mods-config/preprocess/huntgroups" hints = "/etc/freeradius/3.0/mods-config/preprocess/hints" with_ascend_hack = no ascend_channels_per_line = 23 with_ntdomain_hack = no with_specialix_jetstream_hack = no with_cisco_vsa_hack = no with_alvarion_vsa_hack = no } # Loaded module rlm_utf8 # Loading module "utf8" from file /etc/freeradius/3.0/mods-enabled/utf8 # Loaded module rlm_expiration # Loading module "expiration" from file /etc/freeradius/3.0/mods-enabled/expiration # Loaded module rlm_passwd # Loading module "etc_passwd" from file /etc/freeradius/3.0/mods-enabled/passwd passwd etc_passwd { filename = "/etc/passwd" format = "*User-Name:Crypt-Password:" delimiter = ":" ignore_nislike = no ignore_empty = yes allow_multiple_keys = no hash_size = 100 } # Loaded module rlm_digest # Loading module "digest" from file /etc/freeradius/3.0/mods-enabled/digest # Loaded module rlm_linelog # Loading module "linelog" from file /etc/freeradius/3.0/mods-enabled/linelog linelog { filename = "/var/log/freeradius/linelog" escape_filenames = no syslog_severity = "info" permissions = 384 format = "This is a log message for %{User-Name}" reference = "messages.%{%{reply:Packet-Type}:-default}" } # Loading module "log_accounting" from file /etc/freeradius/3.0/mods-enabled/linelog linelog log_accounting { filename = "/var/log/freeradius/linelog-accounting" escape_filenames = no syslog_severity = "info" permissions = 384 format = "" reference = "Accounting-Request.%{%{Acct-Status-Type}:-unknown}" } # Loading module "ntlm_auth" from file /etc/freeradius/3.0/mods-enabled/ntlm_auth exec ntlm_auth { wait = yes program = "/path/to/ntlm_auth --request-nt-key --domain=MYDOMAIN --username=%{mschap:User-Name} --password=%{User-Password}" shell_escape = yes } # Loaded module rlm_unix # Loading module "unix" from file /etc/freeradius/3.0/mods-enabled/unix unix { radwtmp = "/var/log/freeradius/radwtmp" } Creating attribute Unix-Group # Loaded module rlm_always # Loading module "reject" from file /etc/freeradius/3.0/mods-enabled/always always reject { rcode = "reject" simulcount = 0 mpp = no } # Loading module "fail" from file /etc/freeradius/3.0/mods-enabled/always always fail { rcode = "fail" simulcount = 0 mpp = no } # Loading module "ok" from file /etc/freeradius/3.0/mods-enabled/always always ok { rcode = "ok" simulcount = 0 mpp = no } # Loading module "handled" from file /etc/freeradius/3.0/mods-enabled/always always handled { rcode = "handled" simulcount = 0 mpp = no } # Loading module "invalid" from file /etc/freeradius/3.0/mods-enabled/always always invalid { rcode = "invalid" simulcount = 0 mpp = no } # Loading module "userlock" from file /etc/freeradius/3.0/mods-enabled/always always userlock { rcode = "userlock" simulcount = 0 mpp = no } # Loading module "notfound" from file /etc/freeradius/3.0/mods-enabled/always always notfound { rcode = "notfound" simulcount = 0 mpp = no } # Loading module "noop" from file /etc/freeradius/3.0/mods-enabled/always always noop { rcode = "noop" simulcount = 0 mpp = no } # Loading module "updated" from file /etc/freeradius/3.0/mods-enabled/always always updated { rcode = "updated" simulcount = 0 mpp = no } # Loading module "auth_log" from file /etc/freeradius/3.0/mods-enabled/detail.log detail auth_log { filename = "/var/log/freeradius/radacct/%{%{Packet-Src-IP-Address}:-%{Packet-Src-IPv6-Address}}/auth-detail-%Y%m%d" header = "%t" permissions = 384 locking = no escape_filenames = no log_packet_header = no } # Loading module "reply_log" from file /etc/freeradius/3.0/mods-enabled/detail.log detail reply_log { filename = "/var/log/freeradius/radacct/%{%{Packet-Src-IP-Address}:-%{Packet-Src-IPv6-Address}}/reply-detail-%Y%m%d" header = "%t" permissions = 384 locking = no escape_filenames = no log_packet_header = no } # Loading module "pre_proxy_log" from file /etc/freeradius/3.0/mods-enabled/detail.log detail pre_proxy_log { filename = "/var/log/freeradius/radacct/%{%{Packet-Src-IP-Address}:-%{Packet-Src-IPv6-Address}}/pre-proxy-detail-%Y%m%d" header = "%t" permissions = 384 locking = no escape_filenames = no log_packet_header = no } # Loading module "post_proxy_log" from file /etc/freeradius/3.0/mods-enabled/detail.log detail post_proxy_log { filename = "/var/log/freeradius/radacct/%{%{Packet-Src-IP-Address}:-%{Packet-Src-IPv6-Address}}/post-proxy-detail-%Y%m%d" header = "%t" permissions = 384 locking = no escape_filenames = no log_packet_header = no } # Loaded module rlm_eap # Loading module "eap" from file /etc/freeradius/3.0/mods-enabled/eap eap { default_eap_type = "ttls" timer_expire = 60 ignore_unknown_eap_types = no cisco_accounting_username_bug = no max_sessions = 16384 } # Loaded module rlm_expr # Loading module "expr" from file /etc/freeradius/3.0/mods-enabled/expr expr { safe_characters = "@abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789.-_: /äéöüàâæçèéêëîïôœùûüaÿÄÉÖÜßÀ ÆÇÈÉÊËÎÏÔŒÙÛÜŸ" } # Loaded module rlm_files # Loading module "files" from file /etc/freeradius/3.0/mods-enabled/files files { filename = "/etc/freeradius/3.0/mods-config/files/authorize" acctusersfile = "/etc/freeradius/3.0/mods-config/files/accounting" preproxy_usersfile = "/etc/freeradius/3.0/mods-config/files/pre-proxy" } instantiate { } # Instantiating module "detail" from file /etc/freeradius/3.0/mods-enabled/detail # Instantiating module "ldap" from file /etc/freeradius/3.0/mods-enabled/ldap rlm_ldap: libldap vendor: OpenLDAP, version: 20449 accounting { reference = "%{tolower:type.%{Acct-Status-Type}}" } post-auth { reference = "." } rlm_ldap (ldap): Initialising connection pool pool { start = 5 min = 3 max = 32 spare = 10 uses = 0 lifetime = 0 cleanup_interval = 30 idle_timeout = 60 retry_delay = 30 spread = no } rlm_ldap (ldap): Opening additional connection (0), 1 of 32 pending slots used rlm_ldap (ldap): Connecting to ldaps://ldap.google.com:636 TLS: can't connect: (unknown error code). rlm_ldap (ldap): Bind with admin@foundationacademy.net to ldaps://ldap.google.com:636 failed: Can't contact LDAP server rlm_ldap (ldap): Opening connection failed (0) rlm_ldap (ldap): Removing connection pool /etc/freeradius/3.0/mods-enabled/ldap[8]: Instantiation failed for module "ldap"