So i have set up an openldap server using this guide here. It worked fine. But as i want to use sssd i also need TLS to be working for ldap. So i looked into and followed the TLS part of the guide. And i never got any errors and slapd started fine again. BUT. It does not seem to work when i try to use ldap over tls. root@server:~# ldapsearch -x -ZZ -H ldap://83.209.243.253 -b dc=daladevelop,dc=se ldap_start_tls: Protocol error (2) additional info: unsupported extended operation Ganking up the debug level some notches returns some more information: root@server:~# ldapsearch -x -ZZ -H ldap://83.209.243.253 -b dc=daladevelop,dc=se -d 5 ldap_url_parse_ext(ldap://83.209.243.253) ldap_create ldap_url_parse_ext(ldap://83.209.243.253:389/??base) ldap_extended_operation_s ldap_extended_operation ldap_send_initial_request ldap_new_connection 1 1 0 ldap_int_open_connection ldap_connect_to_host: TCP 83.209.243.253:389 ldap_new_socket: 3 ldap_prepare_socket: 3 ldap_connect_to_host: Trying 83.209.243.253:389 ldap_pvt_connect: fd: 3 tm: -1 async: 0 ldap_open_defconn: successful ldap_send_server_request ber_scanf fmt ({it) ber: ber_scanf fmt ({) ber: ber_flush2: 31 bytes to sd 3 ldap_result ld 0x7f25df51e220 msgid 1 wait4msg ld 0x7f25df51e220 msgid 1 (infinite timeout) wait4msg continue ld 0x7f25df51e220 msgid 1 all 1 ** ld 0x7f25df51e220 Connections: * host: 83.209.243.253 port: 389 (default) refcnt: 2 status: Connected last used: Fri Jun 6 08:52:16 2014 ** ld 0x7f25df51e220 Outstanding Requests: * msgid 1, origid 1, status InProgress outstanding referrals 0, parent count 0 ld 0x7f25df51e220 request count 1 (abandoned 0) ** ld 0x7f25df51e220 Response Queue: Empty ld 0x7f25df51e220 response count 0 ldap_chkResponseList ld 0x7f25df51e220 msgid 1 all 1 ldap_chkResponseList returns ld 0x7f25df51e220 NULL ldap_int_select read1msg: ld 0x7f25df51e220 msgid 1 all 1 ber_get_next ber_get_next: tag 0x30 len 42 contents: read1msg: ld 0x7f25df51e220 msgid 1 message type extended-result ber_scanf fmt ({eAA) ber: read1msg: ld 0x7f25df51e220 0 new referrals read1msg: mark request completed, ld 0x7f25df51e220 msgid 1 request done: ld 0x7f25df51e220 msgid 1 res_errno: 2, res_error: <unsupported extended operation>, res_matched: <> ldap_free_request (origid 1, msgid 1) ldap_parse_extended_result ber_scanf fmt ({eAA) ber: ldap_parse_result ber_scanf fmt ({iAA) ber: ber_scanf fmt (}) ber: ldap_msgfree ldap_err2string ldap_start_tls: Protocol error (2) additional info: unsupported extended operation ldap_free_connection 1 1 ldap_send_unbind ber_flush2: 7 bytes to sd 3 ldap_free_connection: actually freed So no good information there neither. In /var/log/syslog i get: Jun 6 08:55:42 master slapd[21383]: conn=1008 fd=23 ACCEPT from IP=83.209.243.253:56440 (IP=0.0.0.0:389) Jun 6 08:55:42 master slapd[21383]: conn=1008 op=0 EXT oid=1.3.6.1.4.1.1466.20037 Jun 6 08:55:42 master slapd[21383]: conn=1008 op=0 do_extended: unsupported operation "1.3.6.1.4.1.1466.20037" Jun 6 08:55:42 master slapd[21383]: conn=1008 op=0 RESULT tag=120 err=2 text=unsupported extended operation Jun 6 08:55:42 master slapd[21383]: conn=1008 op=1 UNBIND Jun 6 08:55:42 master slapd[21383]: conn=1008 fd=23 closed If i portscan the host i get the following: Starting Nmap 6.40 ( http://nmap.org ) at 2014-06-06 08:56 CEST Nmap scan report for h83-209-243-253.static.se.alltele.net (83.209.243.253) Host is up (0.0072s latency). Not shown: 996 closed ports PORT STATE SERVICE 22/tcp open ssh 80/tcp open http 389/tcp open ldap 636/tcp open ldapssl But when i check certs root@master:~# openssl s_client -connect daladevelop.se:636 -showcerts -state CONNECTED(00000003) SSL_connect:before/connect initialization SSL_connect:unknown state 140244859233952:error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure:s23_lib.c:177: --- no peer certificate available --- No client certificate CA names sent --- SSL handshake has read 0 bytes and written 317 bytes --- New, (NONE), Cipher is (NONE) Secure Renegotiation IS NOT supported Compression: NONE Expansion: NONE --- And i feel like i am clearly out in deep water not knowing at all where to go from here. Anny hints appreciated on what to do or to get better debug logging... EDIT: This is my config slapcated from cn=config and it does not mention at all anything about TLS. I have inserted my certinfo.ldif: root@master:~# cat certinfo.ldif dn: cn=config add: olcTLSCACertificateFile olcTLSCACertificateFile: /etc/ssl/certs/cacert.pem - add: olcTLSCertificateFile olcTLSCertificateFile: /etc/ssl/certs/daladevelop_slapd_cert.pem - add: olcTLSCertificateKeyFile olcTLSCertificateKeyFile: /etc/ssl/private/daladevelop_slapd_key.pem and when doing that i only got this as an answer. root@master:~# sudo ldapmodify -Y EXTERNAL -H ldapi:/// -f certinfo.ldif SASL/EXTERNAL authentication started SASL username: gidNumber=0+uidNumber=0,cn=peercred,cn=external,cn=auth SASL SSF: 0 modifying entry "cn=config" So still no wiser.