Bug#403583: exim4: client TLS authentication is broken

[Celejar]

Package: exim4
Version: 4.63-2
Severity: normal

*** Please type your report below this line ***

Exim is set to relay outgoing mail through a smarthost (smtp.gmail.com
a.k.a gmail-smtp.l.google.com) which requires the client to authenticate
via TLS. Exim is configured to do so, and /etc/exim4/passwd.client
contains the following lines:

> *:me at gmail.com:my_password
> gmail-smtp.l.google.com:me at gmail.com:my_password
> smtp.gmail.com:me at gmail.com:my_password

Sending mail is often succesful, but it often fails with the
following log message:

> xxxx-xx-xx xx:xx:xx xxxxxxxxxx ** me at gmail.com R=smarthost
> T=remote_smtp_smarthost: SMTP error from remote mail server after MAIL
> FROM:<> SIZE=xxxx: host gmail-smtp.l.google.com [64.233.185.111]: 530
> 5.5.1 Authentication Required xxxxxxxxxx

Other MTAs on the system (Sylpheed, swaks and others) are consistently
successful at relaying mail through the same smarthost.
This problem is discussed at some length on the (regular, non-Debian) exim
mailing list [0], but I see no resolution there.
The information on the "GmailandExim4" page of the Debian wiki [1] also
does not help to resolve the problem.

[0] http://www.exim.org/mail-archives/exim-users/Week-of-Mon-20061023/msg00323.html
[1] http://wiki.debian.org/GmailAndExim4

Package-specific info:
Exim version 4.63 #1 built 15-Aug-2006 20:40:36
Copyright (c) University of Cambridge 2006
Berkeley DB: Sleepycat Software: Berkeley DB 4.3.29: (September  6, 2005)
Support for: crypteq iconv() IPv6 GnuTLS move_frozen_messages
Lookups: lsearch wildlsearch nwildlsearch iplsearch cdb dbm dbmnz dsearch nis nis0 passwd
Authenticators: cram_md5 plaintext
Routers: accept dnslookup ipliteral manualroute queryprogram redirect
Transports: appendfile/maildir/mailstore autoreply lmtp pipe smtp
Fixed never_users: 0
Size of off_t: 8
Configuration file is /var/lib/exim4/config.autogenerated
# /etc/exim4/update-exim4.conf.conf
#
# Edit this file and /etc/mailname by hand and execute update-exim4.conf
# yourself or use 'dpkg-reconfigure exim4-config'
#
# Please note that this is _not_ a dpkg-conffile and that automatic changes
# to this file might happen. The code handling this will honor your local
# changes, so this is usually fine, but will break local schemes that mess
# around with multiple versions of the file.
#
# update-exim4.conf uses this file to determine variable values to replace
# the DEBCONFsomethingDEBCONF strings in the configuration template files.
#
# Most settings found in here do have corresponding questions in the
# Debconf configuration, but not all of them.
#
# This is a Debian specific file

dc_eximconfig_configtype='smarthost'
dc_other_hostnames='localhost.localdomain'
dc_local_interfaces='127.0.0.1'
dc_readhost=''
dc_relay_domains=''
dc_minimaldns='false'
dc_relay_nets=''
dc_smarthost='smtp.gmail.com'
CFILEMODE='644'
dc_use_split_config='true'
dc_hide_mailname='false'
dc_mailname_in_oh='true'
mailname:localhost.localdomain

-- System Information:
Debian Release: 3.1
  APT prefers unstable
  APT policy: (500, 'unstable')
Architecture: i386 (i586)
Shell:  /bin/sh linked to /bin/bash
Kernel: Linux 2.4.27-2-386
Locale: LANG=en_US, LC_CTYPE=en_US (charmap=ISO-8859-1)

Versions of packages exim4 depends on:
ii  exim4-base                    4.63-2     support files for all exim MTA (v4
ii  exim4-daemon-light            4.63-2     lightweight exim MTA (v4) daemon

exim4 recommends no packages.

-- no debconf information