Full_Name: Graham Wells Version: 2.4.28 OS: macOS 10.12.1 URL: Submission from: (NULL) (50.207.27.182)

SSLHandshake fails for ldapsearch when the subject is blank, even if the certificate is valid and certificate chain trusted (should only require a valid SAN and for SAN to be marked as critical):

Command: /usr/bin/ldapsearch -b "CN=userid,ou=foo,ou=bar,dc=domain,dc=com" -D "CN=bind-dn,ou=foo,ou=bar,dc=domain,dc=com" -H ldaps://server-ldap.com:636 -W -d-1

ldap_url_parse_ext(ldaps://server-ldap.com:636) ldap_create ldap_url_parse_ext(ldaps://server-ldap.com:636/??base) Enter LDAP Password:AlAldap_sasl_bind ldap_send_initial_request ldap_new_connection 1 1 0 ldap_int_open_connection ldap_connect_to_host: TCP server-ldap.com:636 ldap_new_socket: 3 ldap_prepare_socket: 3 ldap_connect_to_host: Trying 10.2.2.2:636 ldap_pvt_connect: fd: 3 tm: -1 async:%D tlsst_thr_init() tlsst_init() tlsst_ctx_new() = 0x7fa10de02f90 tlsst_ctx_init(0x7fa10de02f90) tlsst_ciphers_get((null), TLS_CIPHER_SUITE) tlsst_trusted_certs_get(CA 002|CA 001|CA 003|ROOT CA 001|Other Root CA, TLS_TRUSTED_CERTS) tlssttetem_get(CA 002, TLS_TRUSTED_CERTS) tlsst_item_get(CA 001, TLS_TRUSTED_CERTS) tlsst_item_get(CA 003, TLS_TRUSTED_CERTS) tlsst_item_get(ROOT CA 001, TLS_TRUSTED_CERTS) tlsst_item_get(Other Root CA, TLS_TRUSTED_CERTS) tlsst_session_new(0x7fa10de02f90) tlsst_ciphers_set(42, TLS_CIPHER_SUITE) TLS: 42 ciphers wanted: ...(omitted) TLS: 72 ciphers supported: ...(omitted) TLS: 16 ciphers enabled ...(omitted) tlsst_ctx_ref(0x7fa10de02f90) tlsst_session_new(0x7fa10de02f90) = 0x7fa10dd08280 tlsst_sb_setup(0x7fa10dd08280) tlsst_ctx_ref(0x7fa10de02f90) tlsst_session_connect(0x7fa10dd08280) tlsst_session_handshake() tlsst_socket_write(0x7fa10dd0ef68, 123) tls_write: want=123, written=123 0000: 16 03 01 00 76 01 00 00 72 03 03 58 33 55 fe 4e ....v...r..X3U.N 0010: 8e 16 0d df 99 3a e6 68 36 a1 ff 90 71 1f 78 bb .....:.h6...q.x. 0020: 70 bf 2a 02 05 44 c9 94 07 33 2f 00 00 22 00 ff p.*..D...3/..".. 0030: 00 9d 00 9f 00 3d 00 6b 00 35 00 39 00 9c 00 9e .....=.k.5.9.... 0040: 00 3c 00 67 00 2f 00 33 00 0a 00 16 00 05 00 04 .<.g./.3........ 0050: 01 00 00 27 00 0d 00 12 00 10 04 01 02 01 05 01 ...'............ 0060: 06 01 04 03 02 03 05 03 06 03 00 05 00 05 01 00 ................ 0070: 00 00 00 00 12 00 00 00 17 00 00 ........... tlsst_socket_read(0x7fa10e81d800, 5) tls_read: want=5, got=5 0000: 16 03 03 11 38 ....8 tlsst_socket_read(0x7fa10e81d805, 4408) tls_read: want=0808, got=2891 ...(sanitized) tlsst_socket_read - received (2891) bytes of (4408) requested bytes - (1517) encrypted bytes remaining tlsst_socket_flags sess(0x7fa10dd08280) tlsst_socket_flags ->(2) tlsst_socket_read(0x7fa10e81e350, 1517) tls_read: want=1517, got=1517 ...(sanitized) TLS: during handshake: peer cert is valid, or was ignored if verification disabled (-9841) TLS: during handshake: Peer certificate is not trusted: kSecTrustResultRecoverableTrustFailure tlsst_session_upflags(0x7fa10dd08280) tlsst_session_errmsg(0x7fa10dd08280) TLS: can't connect: SSLHandshake() failed: misc. bad certificate (-9825). tlsst_sb_remove(0x7fa10dd08280) tlsst_session_free(0x7fa10dd08280) tlsst_ctx_free(0x7fa10de02f90) ldap_err2string ldap_sasl_bind(SIMPLE): Can7t7t contact LDAP server (-1) ldap_pvt_clear_search_results_callback: ld 0x7fa10dd00ab0 ldap_pvt_close_select_pipe: sip = 0x7fa10e803800 tlsst_ctx_free(0x7fa10de02f90) tlsst_ctx_free(0x7fa10de02f90) tlsst_destroy()

Certificate is otherwise valid:

Certificate: Data: Version: 3 (0x2) Serial Number: (redacted) Signature Algorithm: sha256WithRSAEncryption Issuer: DC=foo, DC=bar, CN=CA 003 Validity Not Before: Oct 25 23:33:16 2016 GMT Not After : Oct 25 23:33:16 2017 GMT Subject: Subject Public Key Info: Public Key Algorithm: rsaEncryption RSA Public Key: (2048 bit) Modulus (2048 bit): (redacted) Exponent: 65537 (0x10001) X509v3 extensions: 1.3.6.1.4.1.311.21.7: 0-.%+.....7....`...W......./....W...b......d... X509v3 Extended Key Usage: 1.3.6.1.5.2.3.5, Microsoft Smartcardlogin, TLS Web Server Authentication, TLS Web Client Authentication X509v3 Key Usage: critical Digital Signature, Key Encipherment 1.3.6.1.4.1.311.21.10: 010...+......0.. +.....7...0 ..+.......0 ..+....... X509v3 Subject Key Identifier: E2:D2:D9:24:6D:A6:5A:2D:59:03:08:38:03:AE:E8:F4:2A:EA:EB:9F X509v3 Authority Key Identifier: keyid:16:70:AA:1C:31:53:76:FB:26:B5:B8:EA:FC:76:08:E6:3F:17:0D:2F

X509v3 CRL Distribution Points: URI:http://foo.bar.com/CertData/CA 003.crl URI:ldap:///CN=CA 003,CN=server-ldap,CN=CDP,CN=Public%20Key%20Services,CN=Services,CN=Configuration,DC=domain,DC=co3F3FcertificateRevocationList?base?objectClass=cRLDistributionPoint

Authority Information Access: CA Issuers - URI:http://foo.bar.com/CertData/server-ldap_CA-003.crt CA Issuers - URI:ldap:///CN=CA 003,CN=AIA,CN=Public%20Key%20Services,CN=Services,CN=Configuration,DC=domain,DC=com?cACertificate?base?objectClass=certificationAuthority

X509v3 Subject Alternative Name: critical DNS:server-ldap.com, DNS:domain.com, DNS:DOMAIN Signature Algorithm: sha256WithRSAEncryption (redacted)

The certificate is RFC5280 compliant despite having a blank subject name, specifically:

"If the subject field contains an empty sequence, then the issuing CA MUST include a subjectAltName extension that is marked as critical."

Reissuing the certificate and populating the subject field resolves the issue, but it should not be necessary according to the RFC.