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"