Same thing on bionic now.

a) SSL with incorrect name fails as expected:
ubuntu@bionic-ldap-start-tls-1835181:~$ sudo truncate -s 0 /var/log/syslog 

ubuntu@bionic-ldap-start-tls-1835181:~$ ldapwhoami -x -H 
ldaps://bionic-ldap-start-tls-1835181.lxd
ldap_sasl_bind(SIMPLE): Can't contact LDAP server (-1)

ubuntu@bionic-ldap-start-tls-1835181:~$ ldapwhoami -x -H 
ldaps://bionic-ldap-start-tls-1835181.lxd -d -1 2>&1 | grep ^TLS
TLS: hostname (bionic-ldap-start-tls-1835181.lxd) does not match common name in 
certificate (ubuntu).

ubuntu@bionic-ldap-start-tls-1835181:~$ tail /var/log/syslog 
Jul  9 21:02:07 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1015 fd=14 
ACCEPT from IP=10.0.100.234:45518 (IP=0.0.0.0:636)
Jul  9 21:02:07 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1015 fd=14 TLS 
established tls_ssf=256 ssf=256
Jul  9 21:02:07 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1015 fd=14 
closed (connection lost)
Jul  9 21:02:13 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1016 fd=14 
ACCEPT from IP=10.0.100.234:45520 (IP=0.0.0.0:636)
Jul  9 21:02:13 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1016 fd=14 TLS 
established tls_ssf=256 ssf=256
Jul  9 21:02:13 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1016 fd=14 
closed (connection lost)

b) START_TLS with incorrect hostname fails as expected:
ubuntu@bionic-ldap-start-tls-1835181:~$ sudo truncate -s 0 /var/log/syslog 
ubuntu@bionic-ldap-start-tls-1835181:~$ ldapwhoami -x -ZZ -h 
bionic-ldap-start-tls-1835181.lxd
ldap_start_tls: Connect error (-11)
        additional info: TLS: hostname does not match CN in peer certificate
ubuntu@bionic-ldap-start-tls-1835181:~$ ldapwhoami -x -ZZ -h 
bionic-ldap-start-tls-1835181.lxd -d -1 2>&1 | grep ^TLS
TLS: hostname (bionic-ldap-start-tls-1835181.lxd) does not match common name in 
certificate (ubuntu).
ubuntu@bionic-ldap-start-tls-1835181:~$ tail /var/log/syslog 
Jul  9 21:03:01 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1017 fd=14 TLS 
established tls_ssf=256 ssf=256
Jul  9 21:03:01 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1017 op=1 UNBIND
Jul  9 21:03:01 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1017 fd=14 
closed
Jul  9 21:03:09 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1018 fd=14 
ACCEPT from IP=10.0.100.234:37820 (IP=0.0.0.0:389)
Jul  9 21:03:09 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1018 op=0 EXT 
oid=1.3.6.1.4.1.1466.20037
Jul  9 21:03:09 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1018 op=0 
STARTTLS
Jul  9 21:03:09 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1018 op=0 
RESULT oid= err=0 text=
Jul  9 21:03:09 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1018 fd=14 TLS 
established tls_ssf=256 ssf=256
Jul  9 21:03:09 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1018 op=1 UNBIND
Jul  9 21:03:09 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1018 fd=14 
closed


Now the good cases, to show the ssl setup is correct:

a) SSL with ubuntu host:
ubuntu@bionic-ldap-start-tls-1835181:~$ sudo truncate -s 0 /var/log/syslog 
ubuntu@bionic-ldap-start-tls-1835181:~$ ldapwhoami -x -H ldaps://ubuntu/
anonymous
ubuntu@bionic-ldap-start-tls-1835181:~$ tail /var/log/syslog 
Jul  9 21:03:48 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1019 fd=14 
ACCEPT from IP=10.0.100.234:45528 (IP=0.0.0.0:636)
Jul  9 21:03:48 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1019 fd=14 TLS 
established tls_ssf=256 ssf=256
Jul  9 21:03:48 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1019 op=0 BIND 
dn="" method=128
Jul  9 21:03:48 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1019 op=0 
RESULT tag=97 err=0 text=
Jul  9 21:03:48 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1019 op=1 EXT 
oid=1.3.6.1.4.1.4203.1.11.3
Jul  9 21:03:48 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1019 op=1 WHOAMI
Jul  9 21:03:48 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1019 op=1 
RESULT oid= err=0 text=
Jul  9 21:03:48 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1019 op=2 UNBIND
Jul  9 21:03:48 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1019 fd=14 
closed

b) START_TLS with ubuntu host:
ubuntu@bionic-ldap-start-tls-1835181:~$ sudo truncate -s 0 /var/log/syslog 
ubuntu@bionic-ldap-start-tls-1835181:~$ ldapwhoami -x -ZZ -h ubuntu
anonymous
ubuntu@bionic-ldap-start-tls-1835181:~$ tail /var/log/syslog 
Jul  9 21:04:14 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1020 op=0 
STARTTLS
Jul  9 21:04:14 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1020 op=0 
RESULT oid= err=0 text=
Jul  9 21:04:14 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1020 fd=14 TLS 
established tls_ssf=256 ssf=256
Jul  9 21:04:14 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1020 op=1 BIND 
dn="" method=128
Jul  9 21:04:14 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1020 op=1 
RESULT tag=97 err=0 text=
Jul  9 21:04:14 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1020 op=2 EXT 
oid=1.3.6.1.4.1.4203.1.11.3
Jul  9 21:04:14 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1020 op=2 WHOAMI
Jul  9 21:04:14 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1020 op=2 
RESULT oid= err=0 text=
Jul  9 21:04:14 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1020 op=3 UNBIND
Jul  9 21:04:14 bionic-ldap-start-tls-1835181 slapd[2600]: conn=1020 fd=14 
closed


Versions:
slapd:
  Installed: 2.4.45+dfsg-1ubuntu1.2
  Candidate: 2.4.45+dfsg-1ubuntu1.2
  Version table:
 *** 2.4.45+dfsg-1ubuntu1.2 500
        500 http://br.archive.ubuntu.com/ubuntu bionic-updates/main amd64 
Packages

and
libgnutls30:
  Installed: 3.5.18-1ubuntu1.1
  Candidate: 3.5.18-1ubuntu1.1
  Version table:
 *** 3.5.18-1ubuntu1.1 500
        500 http://br.archive.ubuntu.com/ubuntu bionic-updates/main amd64 
Packages


Before I continue testing older releases, is this procedure correct to try to 
reproduce the bug? Maybe I missed something.

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You received this bug notification because you are a member of Ubuntu
Server, which is subscribed to openldap in Ubuntu.
https://bugs.launchpad.net/bugs/1835181

Title:
  OpenLDAP LDAP_OPT_X_TLS_REQUIRE_CERT handling differences between
  ldaps:// and ldap:// with STARTTLS

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