Trying both TLS and TTLS on Macintosh OS X 10.5.5 certificates seem to be fine on both Windows and Macintosh using the ca.der and caclient.p12 (using Ivan's newer script for generating) for TLS Below is radiusd -X log with one failed attempt and it just seems as if the eap challenges go out but responses never come back. LDAP authorizes and authenticates my VPN connections fine, it's just 802.1x that is my problem. Any bone tossed here would be appreciated Craig FreeRADIUS Version 2.1.1, for host i686-redhat-linux-gnu, built on Dec 9 2008 at 20:42:36 Copyright (C) 1999-2008 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 v2. Starting - reading configuration files ... including configuration file /etc/raddb/radiusd.conf including configuration file /etc/raddb/proxy.conf including configuration file /etc/raddb/clients.conf including files in directory /etc/raddb/modules/ including configuration file /etc/raddb/modules/attr_rewrite including configuration file /etc/raddb/modules/ldap including configuration file /etc/raddb/modules/mschap including configuration file /etc/raddb/modules/checkval including configuration file /etc/raddb/modules/expiration including configuration file /etc/raddb/modules/linelog including configuration file /etc/raddb/modules/pam including configuration file /etc/raddb/modules/mac2vlan including configuration file /etc/raddb/modules/passwd including configuration file /etc/raddb/modules/attr_filter including configuration file /etc/raddb/modules/realm including configuration file /etc/raddb/modules/always including configuration file /etc/raddb/modules/mschap-dist including configuration file /etc/raddb/modules/preprocess-dist including configuration file /etc/raddb/modules/detail.example.com including configuration file /etc/raddb/modules/sradutmp including configuration file /etc/raddb/modules/mac2ip including configuration file /etc/raddb/modules/realm-dist including configuration file /etc/raddb/modules/smbpasswd including configuration file /etc/raddb/modules/preprocess including configuration file /etc/raddb/modules/expr including configuration file /etc/raddb/modules/radutmp including configuration file /etc/raddb/modules/sql_log including configuration file /etc/raddb/modules/acct_unique including configuration file /etc/raddb/modules/wimax including configuration file /etc/raddb/modules/files including configuration file /etc/raddb/modules/inner-eap-dist including configuration file /etc/raddb/modules/counter including configuration file /etc/raddb/modules/policy including configuration file /etc/raddb/modules/digest including configuration file /etc/raddb/modules/ippool including configuration file /etc/raddb/modules/logintime including configuration file /etc/raddb/modules/etc_group including configuration file /etc/raddb/modules/detail including configuration file /etc/raddb/modules/pap including configuration file /etc/raddb/modules/echo including configuration file /etc/raddb/modules/exec including configuration file /etc/raddb/modules/detail.log including configuration file /etc/raddb/modules/chap including configuration file /etc/raddb/modules/unix including configuration file /etc/raddb/modules/inner-eap including configuration file /etc/raddb/eap.conf including configuration file /etc/raddb/policy.conf including files in directory /etc/raddb/sites-enabled/ including configuration file /etc/raddb/sites-enabled/inner-tunnel including configuration file /etc/raddb/sites-enabled/control-socket including configuration file /etc/raddb/sites-enabled/default group = radiusd user = radiusd including dictionary file /etc/raddb/dictionary main { prefix = "/usr" localstatedir = "/var" logdir = "/var/log/radius" libdir = "/usr/lib/freeradius" radacctdir = "/var/log/radius/radacct" hostname_lookups = no max_request_time = 30 cleanup_delay = 5 max_requests = 1024 allow_core_dumps = no pidfile = "/var/run/radiusd/radiusd.pid" checkrad = "/usr/sbin/checkrad" debug_level = 0 proxy_requests = yes log { stripped_names = no auth = yes auth_badpass = yes auth_goodpass = no } security { max_attributes = 200 reject_delay = 1 status_server = yes } } client localhost { ipaddr = 127.0.0.1 require_message_authenticator = no secret = "$OBSCURED" nastype = "other" } client 192.168.100.9/32 { require_message_authenticator = no secret = "$OBSCURED" shortname = "RRAS" } client 192.168.10.251/32 { require_message_authenticator = no secret = "$OBSCURED" shortname = "WAP-2" } client 192.168.10.250/32 { require_message_authenticator = no secret = "$OBSCURED" shortname = "WAP-1" } client 192.168.100.7/32 { require_message_authenticator = no secret = "$OBSCURED" shortname = "Test" } client 192.168.10.7/32 { require_message_authenticator = no secret = "$OBSCURED" shortname = "Test" } 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 = "testing123" response_window = 20 max_outstanding = 65536 zombie_period = 40 status_check = "status-server" ping_interval = 30 check_interval = 30 num_answers_to_alive = 3 num_pings_to_alive = 3 revive_interval = 120 status_check_timeout = 4 } home_server_pool my_auth_failover { type = fail-over home_server = localhost } realm example.com { auth_pool = my_auth_failover } realm LOCAL { } radiusd: #### Instantiating modules #### instantiate { Module: Linked to module rlm_exec Module: Instantiating exec exec { wait = no input_pairs = "request" shell_escape = yes } Module: Linked to module rlm_expr Module: Instantiating expr Module: Linked to module rlm_expiration Module: Instantiating expiration expiration { reply-message = "Password Has Expired " } Module: Linked to module rlm_logintime Module: Instantiating logintime logintime { reply-message = "You are calling outside your allowed timespan " minimum-timeout = 60 } } radiusd: #### Loading Virtual Servers #### server inner-tunnel { modules { Module: Checking authenticate {...} for more modules to load Module: Linked to module rlm_pap Module: Instantiating pap pap { encryption_scheme = "auto" auto_header = no } Module: Linked to module rlm_chap Module: Instantiating chap Module: Linked to module rlm_mschap Module: Instantiating mschap mschap { use_mppe = yes require_encryption = yes require_strong = yes with_ntdomain_hack = yes } Module: Linked to module rlm_unix Module: Instantiating unix unix { radwtmp = "/var/log/radius/radwtmp" } Module: Linked to module rlm_ldap Module: Instantiating ldap ldap { server = "localhost" port = 389 password = "$OBSCURED" identity = "cn=admin,o=Company,c=US" net_timeout = 1 timeout = 4 timelimit = 3 tls_mode = no start_tls = no tls_require_cert = "allow" basedn = "ou=People,ou=Accounts,o=Company,c=US" filter = "(uid=%{Stripped-User-Name:-%{User-Name}})" base_filter = "(objectclass=radiusprofile)" password_attribute = "userPassword" auto_header = no access_attr = "uid" access_attr_used_for_allow = yes groupname_attribute = "cn" groupmembership_filter = "(&(objectClass=PosixGroup)(memberUID= %{Stripped-User-Name:-%{User-Name}}))" groupmembership_attribute = "users-remote" dictionary_mapping = "/etc/raddb/ldap.attrmap" ldap_debug = 0 ldap_connections_number = 5 compare_check_items = no do_xlat = yes set_auth_type = yes } rlm_ldap: Registering ldap_groupcmp for Ldap-Group rlm_ldap: Registering ldap_xlat with xlat_name ldap rlm_ldap: reading ldap<->radius mappings from file /etc/raddb/ldap.attrmap rlm_ldap: LDAP radiusCheckItem mapped to RADIUS $GENERIC$ rlm_ldap: LDAP radiusReplyItem mapped to RADIUS $GENERIC$ rlm_ldap: LDAP radiusAuthType mapped to RADIUS Auth-Type rlm_ldap: LDAP radiusSimultaneousUse mapped to RADIUS Simultaneous-Use rlm_ldap: LDAP radiusCalledStationId mapped to RADIUS Called-Station-Id rlm_ldap: LDAP radiusCallingStationId mapped to RADIUS Calling-Station-Id rlm_ldap: LDAP lmPassword mapped to RADIUS LM-Password rlm_ldap: LDAP ntPassword mapped to RADIUS NT-Password rlm_ldap: LDAP sambaLmPassword mapped to RADIUS LM-Password rlm_ldap: LDAP sambaNtPassword mapped to RADIUS NT-Password rlm_ldap: LDAP dBCSPwd mapped to RADIUS LM-Password rlm_ldap: LDAP acctFlags mapped to RADIUS SMB-Account-CTRL-TEXT rlm_ldap: LDAP radiusExpiration mapped to RADIUS Expiration rlm_ldap: LDAP radiusNASIpAddress mapped to RADIUS NAS-IP-Address rlm_ldap: LDAP radiusServiceType mapped to RADIUS Service-Type rlm_ldap: LDAP radiusFramedProtocol mapped to RADIUS Framed-Protocol rlm_ldap: LDAP radiusFramedIPAddress mapped to RADIUS Framed-IP-Address rlm_ldap: LDAP radiusFramedIPNetmask mapped to RADIUS Framed-IP-Netmask rlm_ldap: LDAP radiusFramedRoute mapped to RADIUS Framed-Route rlm_ldap: LDAP radiusFramedRouting mapped to RADIUS Framed-Routing rlm_ldap: LDAP radiusFilterId mapped to RADIUS Filter-Id rlm_ldap: LDAP radiusFramedMTU mapped to RADIUS Framed-MTU rlm_ldap: LDAP radiusFramedCompression mapped to RADIUS Framed-Compression rlm_ldap: LDAP radiusLoginIPHost mapped to RADIUS Login-IP-Host rlm_ldap: LDAP radiusLoginService mapped to RADIUS Login-Service rlm_ldap: LDAP radiusLoginTCPPort mapped to RADIUS Login-TCP-Port rlm_ldap: LDAP radiusCallbackNumber mapped to RADIUS Callback-Number rlm_ldap: LDAP radiusCallbackId mapped to RADIUS Callback-Id rlm_ldap: LDAP radiusFramedIPXNetwork mapped to RADIUS Framed-IPX-Network rlm_ldap: LDAP radiusClass mapped to RADIUS Class rlm_ldap: LDAP radiusSessionTimeout mapped to RADIUS Session-Timeout rlm_ldap: LDAP radiusIdleTimeout mapped to RADIUS Idle-Timeout rlm_ldap: LDAP radiusTerminationAction mapped to RADIUS Termination-Action rlm_ldap: LDAP radiusLoginLATService mapped to RADIUS Login-LAT-Service rlm_ldap: LDAP radiusLoginLATNode mapped to RADIUS Login-LAT-Node rlm_ldap: LDAP radiusLoginLATGroup mapped to RADIUS Login-LAT-Group rlm_ldap: LDAP radiusFramedAppleTalkLink mapped to RADIUS Framed-AppleTalk-Link rlm_ldap: LDAP radiusFramedAppleTalkNetwork mapped to RADIUS Framed-AppleTalk-Network rlm_ldap: LDAP radiusFramedAppleTalkZone mapped to RADIUS Framed-AppleTalk-Zone rlm_ldap: LDAP radiusPortLimit mapped to RADIUS Port-Limit rlm_ldap: LDAP radiusLoginLATPort mapped to RADIUS Login-LAT-Port rlm_ldap: LDAP radiusReplyMessage mapped to RADIUS Reply-Message conns: 0x95f6988 Module: Linked to module rlm_eap Module: Instantiating eap eap { default_eap_type = "md5" timer_expire = 60 ignore_unknown_eap_types = no cisco_accounting_username_bug = no max_sessions = 2048 } Module: Linked to sub-module rlm_eap_md5 Module: Instantiating eap-md5 Module: Linked to sub-module rlm_eap_leap Module: Instantiating eap-leap Module: Linked to sub-module rlm_eap_gtc Module: Instantiating eap-gtc gtc { challenge = "Password: " auth_type = "PAP" } Module: Linked to sub-module rlm_eap_tls Module: Instantiating eap-tls tls { rsa_key_exchange = no dh_key_exchange = yes rsa_key_length = 512 dh_key_length = 512 verify_depth = 0 pem_file_type = yes private_key_file = "/etc/raddb/certs/server.pem" certificate_file = "/etc/raddb/certs/server.pem" CA_file = "/etc/raddb/certs/ca.pem" private_key_password = "$OBSCURED" dh_file = "/etc/raddb/certs/dh" random_file = "/etc/raddb/certs/random" fragment_size = 1024 include_length = yes check_crl = no cipher_list = "DEFAULT" make_cert_command = "/etc/raddb/certs/bootstrap" cache { enable = no lifetime = 24 max_entries = 255 } } Module: Linked to sub-module rlm_eap_ttls Module: Instantiating eap-ttls ttls { default_eap_type = "md5" copy_request_to_tunnel = yes use_tunneled_reply = yes virtual_server = "inner-tunnel" } Module: Linked to sub-module rlm_eap_peap Module: Instantiating eap-peap peap { default_eap_type = "mschapv2" copy_request_to_tunnel = no use_tunneled_reply = yes proxy_tunneled_request_as_eap = no virtual_server = "inner-tunnel" } Module: Linked to sub-module rlm_eap_mschapv2 Module: Instantiating eap-mschapv2 mschapv2 { with_ntdomain_hack = no } Module: Checking authorize {...} for more modules to load Module: Linked to module rlm_realm Module: Instantiating suffix realm suffix { format = "suffix" delimiter = "@" ignore_default = no ignore_null = no } Module: Linked to module rlm_files Module: Instantiating files files { usersfile = "/etc/raddb/users" acctusersfile = "/etc/raddb/acct_users" preproxy_usersfile = "/etc/raddb/preproxy_users" compat = "no" } Module: Checking session {...} for more modules to load Module: Linked to module rlm_radutmp Module: Instantiating radutmp radutmp { filename = "/var/log/radius/radutmp" username = "%{User-Name}" case_sensitive = yes check_with_nas = yes perm = 384 callerid = yes } Module: Checking post-proxy {...} for more modules to load Module: Checking post-auth {...} for more modules to load Module: Linked to module rlm_attr_filter Module: Instantiating attr_filter.access_reject attr_filter attr_filter.access_reject { attrsfile = "/etc/raddb/attrs.access_reject" key = "%{User-Name}" } } } modules { Module: Checking authenticate {...} for more modules to load Module: Checking authorize {...} for more modules to load Module: Linked to module rlm_preprocess Module: Instantiating preprocess preprocess { huntgroups = "/etc/raddb/huntgroups" hints = "/etc/raddb/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 } Module: Linked to module rlm_detail Module: Instantiating auth_log detail auth_log { detailfile = "/var/log/radius/radacct/%{Client-IP-Address}/auth-detail-%Y%m%d" header = "%t" detailperm = 384 dirperm = 493 locking = no log_packet_header = no } Module: Checking preacct {...} for more modules to load Module: Linked to module rlm_acct_unique Module: Instantiating acct_unique acct_unique { key = "User-Name, Acct-Session-Id, NAS-IP-Address, Client-IP-Address, NAS-Port" } Module: Checking accounting {...} for more modules to load Module: Instantiating detail detail { detailfile = "/var/log/radius/radacct/%{Client-IP-Address}/detail-%Y%m% d" header = "%t" detailperm = 384 dirperm = 493 locking = no log_packet_header = no } Module: Instantiating attr_filter.accounting_response attr_filter attr_filter.accounting_response { attrsfile = "/etc/raddb/attrs.accounting_response" key = "%{User-Name}" } Module: Checking session {...} for more modules to load Module: Checking post-proxy {...} for more modules to load Module: Checking post-auth {...} for more modules to load } radiusd: #### Opening IP addresses and Ports #### listen { type = "auth" ipaddr = * port = 0 } listen { type = "acct" ipaddr = * port = 0 } listen { type = "control" listen { socket = "/var/run/radiusd/radiusd.sock" } } Listening on authentication address * port 1812 Listening on accounting address * port 1813 Listening on command file /var/run/radiusd/radiusd.sock Listening on proxy address * port 1814 Ready to process requests. rad_recv: Access-Request packet from host 192.168.10.251 port 2054, id=2, length=143 User-Name = "spare" NAS-IP-Address = 192.168.10.251 NAS-Port = 0 Called-Station-Id = "00-21-29-E3-D1-8A" Calling-Station-Id = "00-1F-5B-CB-1C-DB" Framed-MTU = 1400 NAS-Port-Type = Wireless-802.11 Connect-Info = "CONNECT 11Mbps 802.11b" EAP-Message = 0x02e5000a017370617265 Message-Authenticator = 0xd54f005ed1a17b4b96c8f2875e2a4e95 +- entering group authorize {...} ++[preprocess] returns ok [auth_log] expand: /var/log/radius/radacct/%{Client-IP-Address}/auth-detail-%Y%m%d -> /var/log/radius/radacct/192.168.10.251/auth-detail-20090413 [auth_log] /var/log/radius/radacct/%{Client-IP-Address}/auth-detail-%Y%m %d expands to /var/log/radius/radacct/192.168.10.251/auth-detail-20090413 [auth_log] expand: %t -> Mon Apr 13 11:39:49 2009 ++[auth_log] returns ok ++[chap] returns noop ++[mschap] returns noop [suffix] No '@' in User-Name = "spare", looking up realm NULL [suffix] No such realm "NULL" ++[suffix] returns noop [eap] EAP packet type response id 229 length 10 [eap] No EAP Start, assuming it's an on-going EAP conversation ++[eap] returns updated ++[files] returns noop [ldap] performing user authorization for spare [ldap] WARNING: Deprecated conditional expansion ":-". See "man unlang" for details [ldap] expand: (uid=%{Stripped-User-Name:-%{User-Name}}) -> (uid=spare) [ldap] expand: ou=People,ou=Accounts,o=Company,c=US -> ou=People,ou=Accounts,o=Company,c=US rlm_ldap: ldap_get_conn: Checking Id: 0 rlm_ldap: ldap_get_conn: Got Id: 0 rlm_ldap: attempting LDAP reconnection rlm_ldap: (re)connect to localhost:389, authentication 0 rlm_ldap: bind as cn=admin,o=Company,c=US/$OBSCURED to localhost:389 rlm_ldap: waiting for bind result ... rlm_ldap: Bind was successful rlm_ldap: performing search in ou=People,ou=Accounts,o=Company,c=US, with filter (uid=spare) [ldap] checking if remote access for spare is allowed by uid [ldap] Added User-Password = {crypt}$OBSCURED in check items [ldap] looking for check items in directory... rlm_ldap: sambaNtPassword -> NT-Password == 0x$OBSCURED rlm_ldap: sambaLmPassword -> LM-Password == 0x$OBSCURED [ldap] looking for reply items in directory... [ldap] user spare authorized to use remote access rlm_ldap: ldap_release_conn: Release Id: 0 ++[ldap] returns ok ++[expiration] returns noop ++[logintime] returns noop Found Auth-Type = EAP !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!! Replacing User-Password in config items with Cleartext-Password. !!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!! Please update your configuration so that the "known good" !!! !!! clear text password is in Cleartext-Password, and not in User-Password. !!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! +- entering group authenticate {...} [eap] EAP Identity [eap] processing type md5 rlm_eap_md5: Issuing Challenge ++[eap] returns handled Sending Access-Challenge of id 2 to 192.168.10.251 port 2054 EAP-Message = 0x01e600160410f586e30cd2c84a45f7f8a8d753a29f8a Message-Authenticator = 0x00000000000000000000000000000000 State = 0xf43856c6f4de520cc1e0b754fc05eac1 Finished request 0. Going to the next request Waking up in 4.9 seconds. Cleaning up request 0 ID 2 with timestamp +14 Ready to process requests. -- This message has been scanned for viruses and dangerous content by MailScanner, and is believed to be clean.