Hi,

this message ends with a debug output from exim 4.63 (Debian)
delivering via a smarthost router (also quoted at the end) to a host
that requires authentication. Exim is configured to authenticate, and
does this most of the time. Other times, this is what happens:

routed by smarthost router
  host gmail-smtp.l.google.com [209.85.133.111] port=587
  host gmail-smtp.l.google.com [209.85.133.109] port=587
<snip>
remote_smtp_smarthost transport entered
<snip>
Connecting to gmail-smtp.l.google.com [209.85.133.111]:587 ... connected
<snip>
209.85.133.111 in hosts_require_auth? no (option unset)
<snip>
gethostbyname2 looked up these IP addresses:
  name=gmail-smtp.l.google.com address=64.233.185.111
  name=gmail-smtp.l.google.com address=64.233.185.109
209.85.133.111 in hosts_try_auth? no (end of list)

Exim then continues to send the message unauthenticated and gets it
rejected.

Is it really possible that exim gets different results for the two
lookups that it does for the host name and in result thinks that it
doesn't need to authenticate?

Do you have any idea what might be going wrong here? And how I can fix
it in the configuration?

Greetings
Marc

router:
smarthost:
  debug_print = "R: smarthost for [EMAIL PROTECTED]"
  driver = manualroute
  domains = ! +local_domains
  transport = remote_smtp_smarthost
  route_list = * DCsmarthost byname
  host_find_failed = defer
  same_domain_copy_routing = yes
  no_more

(the DCsmarthost macro is set to smtp.gmail.com::587)

remote_smtp_smarthost transport:
remote_smtp_smarthost:
  debug_print = "T: remote_smtp_smarthost for [EMAIL PROTECTED]"
  driver = smtp
  hosts_try_auth = ${if exists {CONFDIR/passwd.client}\
                               {${extract{1}{:}{DCsmarthost}}}\
                               {}\
                    }
  tls_tempfail_tryclear = false

CONFDIR/passwd.client exists.

exec /usr/sbin/exim4 -d=0xfbb95cfd -Mc 1H2wDN-0001kT-Qh
Exim version 4.63 uid=102 gid=102 pid=6726 D=fbb95cfd
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
changed uid/gid: forcing real = effective
  uid=0 gid=102 pid=6726
  auxiliary group list: <none>
seeking password data for user "uucp": cache not available
getpwnam() succeeded uid=10 gid=10
configuration file is /var/lib/exim4/config.autogenerated
log selectors = 00000ffc 00189001
cwd=/var/spool/exim4 4 args: /usr/sbin/exim4 -d=0xfbb95cfd -Mc 1H2wDN-0001kT-Qh
trusted user
admin user
skipping ACL configuration - not needed
seeking password data for user "mail": cache not available
getpwnam() succeeded uid=8 gid=8
set_process_info:  6726 delivering specified messages
set_process_info:  6726 delivering 1H2wDN-0001kT-Qh
reading spool file 1H2wDN-0001kT-Qh-H
user=root uid=0 gid=0 [EMAIL PROTECTED]
sender_local=1 ident=root
Non-recipients:
Empty Tree
---- End of tree ----
recipients_count=1
body_linecount=18 message_linecount=14
Delivery address list:
  [EMAIL PROTECTED] 
locking /var/spool/exim4/db/retry.lockfile
locked /var/spool/exim4/db/retry.lockfile
EXIM_DBOPEN(/var/spool/exim4/db/retry)
returned from EXIM_DBOPEN
no retry data available
>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>
Considering: [EMAIL PROTECTED]
unique = [EMAIL PROTECTED]
no domain retry record
no address retry record
[EMAIL PROTECTED]: queued for routing
>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>
routing [EMAIL PROTECTED]
--------> smarthost router <--------
local_part=celejar domain=nerdshack.com
checking domains
nerdshack.com in "@:localhost:localhost.localdomain"? no (end of list)
nerdshack.com in "! +local_domains"? yes (end of list)
R: smarthost for [EMAIL PROTECTED]
calling smarthost router
smarthost router called for [EMAIL PROTECTED]
  domain = nerdshack.com
route_item = * smtp.gmail.com::587 byname
nerdshack.com in "*"? yes (matched "*")
original list of hosts = "smtp.gmail.com::587" options = byname
expanded list of hosts = "smtp.gmail.com::587" options = byname
set transport remote_smtp_smarthost
finding IP address for smtp.gmail.com:587
host=smtp.gmail.com port=587
calling host_find_byname
gethostbyname2(af=inet6) returned 3 (NO_RECOVERY)
fully qualified name = gmail-smtp.l.google.com
gethostbyname2 looked up these IP addresses:
  name=gmail-smtp.l.google.com address=209.85.133.111
  name=gmail-smtp.l.google.com address=209.85.133.109
queued for remote_smtp_smarthost transport: local_part = celejar
domain = nerdshack.com
  errors_to=NULL
  domain_data=NULL localpart_data=NULL
routed by smarthost router
  envelope to: [EMAIL PROTECTED]
  transport: remote_smtp_smarthost
  host gmail-smtp.l.google.com [209.85.133.111] port=587
  host gmail-smtp.l.google.com [209.85.133.109] port=587
>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>
After routing:
  Local deliveries:
  Remote deliveries:
    [EMAIL PROTECTED]
  Failed addresses:
  Deferred addresses:
search_tidyup called
>>>>>>>>>>>>>>>> Remote deliveries >>>>>>>>>>>>>>>>
--------> [EMAIL PROTECTED] <--------
localhost.localdomain in "@:localhost:localhost.localdomain"? yes (matched "@")
localhost.localdomain in "+local_domains"? yes (matched "+local_domains")
search_tidyup called
set_process_info:  6726 delivering 1H2wDN-0001kT-Qh: waiting for a remote 
delivery subprocess to finish
selecting on subprocess pipes
changed uid/gid: remote delivery to [EMAIL PROTECTED] with 
transport=remote_smtp_smarthost
  uid=102 gid=102 pid=6727
  auxiliary group list: <none>
set_process_info:  6727 delivering 1H2wDN-0001kT-Qh using remote_smtp_smarthost
T: remote_smtp_smarthost for [EMAIL PROTECTED]
remote_smtp_smarthost transport entered
  [EMAIL PROTECTED]
nerdshack.com in queue_smtp_domains? no (option unset)
checking status of gmail-smtp.l.google.com
locking /var/spool/exim4/db/retry.lockfile
locked /var/spool/exim4/db/retry.lockfile
EXIM_DBOPEN(/var/spool/exim4/db/retry)
returned from EXIM_DBOPEN
no retry data available
gmail-smtp.l.google.com [209.85.133.111]:587 status = usable
209.85.133.111 in serialize_hosts? no (option unset)
delivering 1H2wDN-0001kT-Qh to gmail-smtp.l.google.com [209.85.133.111] ([EMAIL 
PROTECTED])
set_process_info:  6727 delivering 1H2wDN-0001kT-Qh to gmail-smtp.l.google.com 
[209.85.133.111] ([EMAIL PROTECTED])
Transport port=25 replaced by host-specific port=587
Connecting to gmail-smtp.l.google.com [209.85.133.111]:587 ... connected
waiting for data on socket
read response data: size=40
  SMTP<< 220 mx.google.com ESMTP c9sm2346590ana
209.85.133.111 in hosts_avoid_esmtp? no (option unset)
  SMTP>> EHLO localhost.localdomain
waiting for data on socket
read response data: size=125
  SMTP<< 250-mx.google.com at your service, [70.107.128.254]
         250-SIZE 20971520
         250-8BITMIME
         250-STARTTLS
         250 ENHANCEDSTATUSCODES
209.85.133.111 in hosts_avoid_tls? no (option unset)
  SMTP>> STARTTLS
waiting for data on socket
read response data: size=30
  SMTP<< 220 2.0.0 Ready to start TLS
initializing GnuTLS as a client
read D-H parameters from file
initialized D-H parameters
no TLS client certificate is specified
initialized certificate stuff
initialized GnuTLS session
cipher: TLS-1.0:RSA_3DES_EDE_CBC_SHA1:24
  SMTP>> EHLO localhost.localdomain
tls_do_write(bffbf05c, 28)
gnutls_record_send(SSL, bffbf05c, 28)
outbytes=28
waiting for data on socket
Calling gnutls_record_recv(8123940, bffbd05c, 4096)
read response data: size=133
  SMTP<< 250-mx.google.com at your service, [70.107.128.254]
         250-SIZE 20971520
         250-8BITMIME
         250-AUTH LOGIN PLAIN
         250 ENHANCEDSTATUSCODES
not using PIPELINING
209.85.133.111 in hosts_require_auth? no (option unset)
gethostbyname2(af=inet6) returned 3 (NO_RECOVERY)
gethostbyname2 looked up these IP addresses:
  name=gmail-smtp.l.google.com address=64.233.185.111
  name=gmail-smtp.l.google.com address=64.233.185.109
209.85.133.111 in hosts_try_auth? no (end of list)
  SMTP>> MAIL FROM:<[EMAIL PROTECTED]> SIZE=2675
tls_do_write(bffbf05c, 42)
gnutls_record_send(SSL, bffbf05c, 42)
outbytes=42
waiting for data on socket
Calling gnutls_record_recv(8123940, bffbd05c, 4096)
read response data: size=50
  SMTP<< 530 5.5.1 Authentication Required c9sm2346590ana
ok=0 send_quit=1 send_rset=1 continue_more=0 yield=0 first_address is not NULL
  SMTP>> QUIT
tls_do_write(bffbf05c, 6)
gnutls_record_send(SSL, bffbf05c, 6)
outbytes=6
tls_close(): shutting down TLS
set_process_info:  6727 delivering 1H2wDN-0001kT-Qh: just tried 
gmail-smtp.l.google.com [209.85.133.111] for [EMAIL PROTECTED]: result OK
Leaving remote_smtp_smarthost transport
set_process_info:  6727 delivering 1H2wDN-0001kT-Qh (just run 
remote_smtp_smarthost for [EMAIL PROTECTED] in subprocess)
search_tidyup called
reading pipe for subprocess 6727 (not ended)
read() yielded 5
selecting on subprocess pipes
reading pipe for subprocess 6727 (not ended)
read() yielded 100
selecting on subprocess pipes
reading pipe for subprocess 6727 (not ended)
read() yielded 194
selecting on subprocess pipes
reading pipe for subprocess 6727 (not ended)
read() yielded 2
Z0 item read
remote delivery process 6727 ended
set_process_info:  6726 delivering 1H2wDN-0001kT-Qh
post-process [EMAIL PROTECTED] (2)
LOG: MAIN
  ** [EMAIL PROTECTED] R=smarthost T=remote_smtp_smarthost: SMTP error from 
remote mail server after MAIL FROM:<[EMAIL PROTECTED]> SIZE=2675: host 
gmail-smtp.l.google.com [209.85.133.111]: 530 5.5.1 Authentication Required 
c9sm2346590ana
>>>>>>>>>>>>>>>> deliveries are done >>>>>>>>>>>>>>>>
changed uid/gid: post-delivery tidying
  uid=102 gid=102 pid=6726
  auxiliary group list: <none>
set_process_info:  6726 tidying up after delivering 1H2wDN-0001kT-Qh
Processing retry items
Succeeded addresses:
Failed addresses:
[EMAIL PROTECTED]: no retry items
Deferred addresses:
end of retry processing
processing failed address [EMAIL PROTECTED]
sending error message to: [EMAIL PROTECTED]
writing data block fd=8 size=1661 timeout=0


-- 
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Mannheim, Germany  |  lose things."    Winona Ryder | Fon: *49 621 72739834
Nordisch by Nature |  How to make an American Quilt | Fax: *49 621 72739835

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