I'm working with Ubuntu 12.04, using OpenLDAP server. I've followed the instructions on the Ubuntu help pages and can happily connect without security. To test my connection, I'm using ldapsearch the command looks like: ldapsearch -xv -H ldap://ldap.[my host].local -b dc=[my domain],dc=local -d8 -ZZ I've also used: ldapsearch -xv -H ldaps://ldap.[my host].local -b dc=[my domain],dc=local -d8 As far as I can tell, I've setup my certificate correctly, but no matter why I try, I can't seem to get ldapsearch to accept my self-signed certificate. So far, I've tried: Updating my /etc/ldap/ldap.conf file to look like: BASE dc=[my domain],dc=local URI ldaps://ldap.[my host].local TLS_CACERT /etc/ssl/certs/cacert.crt TLS_REQCERT allow Updating my /etc/ldap.conf file to look like: base dc=[my domain],dc=local uri ldapi:///ldap.[my host].local uri ldaps:///ldap.[my host].local ldap_version 3 ssl start_tls ssl on tls_checkpeer no TLS_REQCERT allow Updating my /etc/default/slapd to include: SLAPD_SERVICES="ldap:/// ldapi:/// ldaps:///" Several hours of Googling, most of which resulted in adding the TLS_REQCERT allow The exact error I'm seeing is: ldap_initialize( ldap://ldap.[my host].local ) request done: ld 0x20038710 msgid 1 TLS certificate verification: Error, self signed certificate in certificate chain TLS: can't connect. ldap_start_tls: Connect error (-11) additional info: error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed After several hours of this, I was hoping someone else has seen this issue, and/or knows how to fix it. Please do let me know if I should add more information, or if you need further data.