[Pkg-exim4-users] getting authentication to work with a smarthost

[Ross Boylan]

I am try to send mail via a smarthost that requires authentication.
Some documentation (dated, I suspect) indicates I should be using port
465, but I am able to connect via 25.  The smarthost advertises
STARTTLS and various authentication mechanisms, and my local exim
seems to recognize that it should try to authenticate.  But as far as
I can tell it neither negotiates TLS nor attempts to authenticate.  It
just tries to deliver the email, which is rejected as unauthenticated.

I would appreciate any help.
<update-exim4.conf.conf>
dc_eximconfig_configtype='smarthost'
dc_other_hostnames='ross-sas.psg.net ross-sas.epi-ucsf.org'
dc_local_interfaces='127.0.0.1 ; ::1'
dc_readhost='ucsf.edu'
dc_relay_domains=''
dc_minimaldns='false'
dc_relay_nets=''
dc_smarthost='mail.ucsf.edu:465'
CFILEMODE='644'
dc_use_split_config='true'
dc_hide_mailname='true'
dc_mailname_in_oh='true'
dc_localdelivery='mail_spool'
</update-exim4.conf.conf>
I have made no customizations beyond running dpkg-reconfigure
exim4-config and putting an entry in passwd.client.

Something, possibly the debconf questions, made me think the single
colon in the smarthost was the proper syntax for specifying an
alternate port.  It seems to have been interpreted as a list separator
and ignored instead; I have since doubled it.  Results at the bottom.

I think the smarthost is running MS Exchange 2012.
# exim -v -t -bm -f "" -d < test.msg
produced lots of output, finally ending up in the
remote_smtp_smarthost transport.  Here's the key section, with my
comments added after the #

Connecting to mail.ucsf.edu [64.54.247.179]:25 ... connected  # Port
25, not the 465 I requested
waiting for data on socket
read response data: size=95
  SMTP<< 220 exht05.net.ucsf.edu Microsoft ESMTP MAIL Service ready at
Mon, 11 Jan 2016 23:00:50 -0800
64.54.247.179 in hosts_avoid_esmtp? no (option unset)  # remote host
name does not match what I used to find it
  SMTP>> EHLO ross-sas  # my local system has no FQDN
waiting for data on socket
read response data: size=201
  SMTP<< 250-STARTTLS
         250-exht05.net.ucsf.edu Hello [64.54.171.2]
         250-SIZE 141557760
         250-PIPELINING
         250-DSN
         250-ENHANCEDSTATUSCODES
         250-AUTH GSSAPI NTLM LOGIN
         250-8BITMIME
         250-BINARYMIME
         250 CHUNKING
64.54.247.179 in hosts_require_tls? no (option unset)
64.54.247.179 in hosts_avoid_pipelining? no (option unset)
using PIPELINING
64.54.247.179 in hosts_require_auth? no (option unset)
search_open: nwildlsearch "/etc/exim4/passwd.client"
search_find: file="/etc/exim4/passwd.client"
  key="mail.ucsf.edu" partial=-1 affix=NULL starflags=0
LRU list:
  >/etc/exim4/passwd.client
  End
internal_search_find: file="/etc/exim4/passwd.client"
  type=nwildlsearch key="mail.ucsf.edu"
file lookup required for mail.ucsf.edu
  in /etc/exim4/passwd.client
mail.ucsf.edu in "mail.ucsf.edu"? yes (matched "mail.ucsf.edu")
lookup yielded: SomeAccount:SomePasword  # Recognizes as configured
for authentication
64.54.247.179 in hosts_try_auth? yes (matched "64.54.247.179")
scanning authentication mechanisms
login authenticator yielded 13   # Not sure what that means
# I would expect the next messages to the smarthost to establish TLS
# and then authenticate.
# But instead, we jump right to a mail command.
# Maybe such negotiations are note reported in the debug output?
# However, the failure of the MAIL command suggests the problem is
# that the commands  were never issued.
  SMTP>> MAIL FROM:<> SIZE=1716
  SMTP>> RCPT TO:<ross.boylan at ucsf.edu>
  SMTP>> DATA
waiting for data on socket
read response data: size=40
  SMTP<< 530 5.7.1 Client was not authenticated
waiting for data on socket
ok=0 send_quit=1 send_rset=1 continue_more=0 yield=0 first_address is not NULL
  SMTP>> QUIT

Thanks.
Ross Boylan

P.S. Running
exim4-daemon-heavy                           4.82-3ubuntu2
exim4-config                                 4.82-3ubuntu2


Doubling the colon in the smarthost spescification gets exim to use
port 465, but:
mail.ucsf.edu [64.54.247.179]:465 status = usable
64.54.247.179 in serialize_hosts? no (option unset)
delivering 1aIufG-00024b-Sq to mail.ucsf.edu [64.54.247.179]
(ross.boylan at ucsf.edu)
set_process_info:  7977 delivering 1aIufG-00024b-Sq to mail.ucsf.edu
[64.54.247.179] (ross.boylan at ucsf.edu)
Transport port=25 replaced by host-specific port=465
Connecting to mail.ucsf.edu [64.54.247.179]:465 ... connected
waiting for data on socket
ok=0 send_quit=0 send_rset=1 continue_more=0 yield=1 first_address is not NULL
LOG: MAIN
  Remote host mail.ucsf.edu [64.54.247.179] closed connection in
response to initial connection
set_process_info:  7977 delivering 1aIufG-00024b-Sq: just tried
mail.ucsf.edu [64.54.247.179] for ross.boylan at ucsf.edu: result DEFER
added retry item for T:mail.ucsf.edu:64.54.247.179:465: errno=-18
more_errno=0,A flags=2
all IP addresses skipped or deferred at least one address