i am seeing the same behavior (tls is not functioning) with
sudo-ldap_1.6.9p17-2_i386.deb.


[21:15:17 t...@jenna:archives]$ sudo ls /
LDAP Config Summary
===================
uri          ldap://host1.oma.example.net ldap://host2.oma.example.net
ldap_version 3
sudoers_base ou=sudoers,ou=oma,dc=example,dc=net
binddn       (anonymous)
bindpw       (anonymous)
bind_timelimit  15000
timelimit    15
ssl          start_tls
tls_checkpeer    (yes)
tls_cacertfile   /etc/ssl/certs/ca.crt
===================
sudo: ldap_initialize(ld, ldap://host1.oma.example.net 
ldap://host2.oma.example.net)
sudo: ldap_set_option: debug -> 0
sudo: ldap_set_option: ldap_version -> 3
sudo: ldap_set_option: tls_checkpeer -> 1
sudo: ldap_set_option: tls_cacertfile -> /etc/ssl/certs/ca.crt
sudo: ldap_set_option: timelimit -> 15
sudo: ldap_set_option(LDAP_OPT_NETWORK_TIMEOUT, 15)

sudo: ldap_start_tls_s(): Connect error


[21:10:52 t...@jenna:archives]$ dpkg -I sudo-ldap_1.6.9p17-2_i386.deb
 new debian package, version 2.0.
 size 188332 bytes: control archive= 2525 bytes.
      33 bytes,     2 lines      conffiles
     642 bytes,    18 lines      control
    1674 bytes,    25 lines      md5sums
    1831 bytes,    64 lines   *  postinst             #!/usr/bin/perl
     170 bytes,     7 lines   *  postrm               #!/bin/sh
     260 bytes,    11 lines   *  prerm                #!/bin/sh
 Package: sudo-ldap
 Source: sudo
 Version: 1.6.9p17-2
 Architecture: i386
 Maintainer: Bdale Garbee <bd...@gag.com>
 Installed-Size: 460
 Depends: libc6 (>= 2.7-1), libldap-2.4-2 (>= 2.4.7), libpam0g (>= 0.99.7.1), 
libpam-modules
 Conflicts: sudo
 Replaces: sudo
 Provides: sudo
 Section: admin
 Priority: optional
 Description: Provide limited super user privileges to specific users
  Sudo is a program designed to allow a sysadmin to give limited root
  privileges to users and log root activity.  The basic philosophy is to give
  as few privileges as possible but still allow people to get their work done.
  .
  This version is built with LDAP support.




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