On Sunday, 4. October 2009, you wrote:
> A couple of things that would explain i can't reproduce :
> - i'm on debian/sid, so maybe there's some problem with the backports;
> please tell me your ruby, rake, liberb-ruby versions

on sid:

sid:/usr/share/redmine# dpkg -l | grep rails
ii  rails 2.2.3-1 MVC ruby based framework geared for web appl
sid:/usr/share/redmine# dpkg -l | grep liberb-ruby
ii  liberb-ruby 4.2 transitional dummy package
sid:/usr/share/redmine# dpkg -l | grep libruby
ii  libruby 4.2 Libraries necessary to run Ruby 1.8.x
ii  libruby1.8 1.8.7.174-2 Libraries necessary to run Ruby 1.8
ii  libruby1.8-extras 0.5 a bundle of additional libraries for Ruby 1.
sid:/usr/share/redmine# dpkg -l | grep " ruby1\."
ii  ruby1.8 1.8.7.174-2 Interpreter of object-oriented scripting lan

> - your mail server is proposing starttls, but has a bad certificate.
> Please try when starttls is disabled in your mail server, or with an
> updated certificate (one with hostname matching it)

You reproduce it with:

sid:/usr/share/redmine# aptitude install postfix
[...]
sid:~# make-ssl-cert generate-default-snakeoil --force-overwrite
sid:/usr/share/redmine# hostname -f
sid.server.earth.cyconet.org
sid:/usr/share/redmine# openssl x509 -in /etc/ssl/certs/ssl-cert-snakeoil.pem 
-noout -text|grep CN=
        Issuer: CN=sid.server.earth.cyconet.org
        Subject: CN=sid.server.earth.cyconet.org
sid:~# /etc/init.d/postfix restart
Stopping Postfix Mail Transport Agent: postfix.
Starting Postfix Mail Transport Agent: postfix.
sid:/usr/share/redmine# grep -v ^# /etc/redmine/default/email.yml
production:
  delivery_method: :smtp
  smtp_settings:
    enable_starttls_auto: false
    address: localhost
    port: 25
    domain: cyconet.org
    authentication: :none
sid:/usr/share/redmine# sudo -u www-data X_DEBIAN_SITEID="default" ruby 
script/server webrick -e production
=> Booting WEBrick...
=> Rails 2.2.3 application started on http://192.168.66.111:3000
=> Ctrl-C to shutdown server; call with --help for options
[2009-10-04 11:30:20] INFO  WEBrick 1.3.1
[2009-10-04 11:30:20] INFO  ruby 1.8.7 (2009-06-12) [i486-linux]
[2009-10-04 11:30:20] INFO  WEBrick::HTTPServer#start: pid=10233 port=3000

http://192.168.66.111:3000/settings/edit?tab=notifications <= hit "Send a test 
email"

192.168.66.115 - - [04/Oct/2009:11:30:29 CEST] "GET /admin/test_email 
HTTP/1.1" 302 124
http://192.168.66.111:3000/settings/edit?tab=notifications -> 
/admin/test_email
192.168.66.115 - - [04/Oct/2009:11:30:29 CEST] "GET 
/settings/edit?tab=notifications HTTP/1.1" 200 27334
http://192.168.66.111:3000/settings/edit?tab=notifications -> 
/settings/edit?tab=notifications

Anyways ... main.cf and master.cf is attached.

> - your mail server is proposing starttls, but has a bad certificate.
> Please try when starttls is disabled in your mail server, or with an
> updated certificate (one with hostname matching it)

With setting "enable_starttls_auto: false" I would expect to not use starttls. 
If that isn't the case, is there any other way to switch tls off, not matter 
if the server supports it or not?

With kind regards, Jan.
-- 
Never write mail to <w...@spamfalle.info>, you have been warned!
-----BEGIN GEEK CODE BLOCK-----
Version: 3.1
GIT d-- s+: a- C+++ UL++++ P+ L+++ E- W+++ N+++ o++ K++ w--- O M V- PS PE
Y++ PGP++ t-- 5 X R tv- b+ DI- D++ G++ e++ h-- r+++ y+++
------END GEEK CODE BLOCK------
# See /usr/share/postfix/main.cf.dist for a commented, more complete version


# Debian specific:  Specifying a file name will cause the first
# line of that file to be used as the name.  The Debian default
# is /etc/mailname.
#myorigin = /etc/mailname

smtpd_banner = $myhostname ESMTP $mail_name (Debian/GNU)
biff = no

# appending .domain is the MUA's job.
append_dot_mydomain = no

# Uncomment the next line to generate "delayed mail" warnings
#delay_warning_time = 4h

readme_directory = no

# TLS parameters
smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem
smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key
smtpd_use_tls=yes
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

# See /usr/share/doc/postfix/TLS_README.gz in the postfix-doc package for
# information on enabling SSL in the smtp client.

myhostname = sid
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
myorigin = /etc/mailname
mydestination = sid.server.earth.cyconet.org, sid, localhost.localdomain, 
localhost
relayhost = 
mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
#
# Postfix master process configuration file.  For details on the format
# of the file, see the master(5) manual page (command: "man 5 master").
#
# Do not forget to execute "postfix reload" after editing this file.
#
# ==========================================================================
# service type  private unpriv  chroot  wakeup  maxproc command + args
#               (yes)   (yes)   (yes)   (never) (100)
# ==========================================================================
smtp      inet  n       -       -       -       -       smtpd
#submission inet n       -       -       -       -       smtpd
#  -o smtpd_tls_security_level=encrypt
#  -o smtpd_sasl_auth_enable=yes
#  -o smtpd_client_restrictions=permit_sasl_authenticated,reject
#  -o milter_macro_daemon_name=ORIGINATING
#smtps     inet  n       -       -       -       -       smtpd
#  -o smtpd_tls_wrappermode=yes
#  -o smtpd_sasl_auth_enable=yes
#  -o smtpd_client_restrictions=permit_sasl_authenticated,reject
#  -o milter_macro_daemon_name=ORIGINATING
#628      inet  n       -       -       -       -       qmqpd
pickup    fifo  n       -       -       60      1       pickup
cleanup   unix  n       -       -       -       0       cleanup
qmgr      fifo  n       -       n       300     1       qmgr
#qmgr     fifo  n       -       -       300     1       oqmgr
tlsmgr    unix  -       -       -       1000?   1       tlsmgr
rewrite   unix  -       -       -       -       -       trivial-rewrite
bounce    unix  -       -       -       -       0       bounce
defer     unix  -       -       -       -       0       bounce
trace     unix  -       -       -       -       0       bounce
verify    unix  -       -       -       -       1       verify
flush     unix  n       -       -       1000?   0       flush
proxymap  unix  -       -       n       -       -       proxymap
proxywrite unix -       -       n       -       1       proxymap
smtp      unix  -       -       -       -       -       smtp
# When relaying mail as backup MX, disable fallback_relay to avoid MX loops
relay     unix  -       -       -       -       -       smtp
        -o smtp_fallback_relay=
#       -o smtp_helo_timeout=5 -o smtp_connect_timeout=5
showq     unix  n       -       -       -       -       showq
error     unix  -       -       -       -       -       error
retry     unix  -       -       -       -       -       error
discard   unix  -       -       -       -       -       discard
local     unix  -       n       n       -       -       local
virtual   unix  -       n       n       -       -       virtual
lmtp      unix  -       -       -       -       -       lmtp
anvil     unix  -       -       -       -       1       anvil
scache    unix  -       -       -       -       1       scache
#
# ====================================================================
# Interfaces to non-Postfix software. Be sure to examine the manual
# pages of the non-Postfix software to find out what options it wants.
#
# Many of the following services use the Postfix pipe(8) delivery
# agent.  See the pipe(8) man page for information about ${recipient}
# and other message envelope options.
# ====================================================================
#
# maildrop. See the Postfix MAILDROP_README file for details.
# Also specify in main.cf: maildrop_destination_recipient_limit=1
#
maildrop  unix  -       n       n       -       -       pipe
  flags=DRhu user=vmail argv=/usr/bin/maildrop -d ${recipient}
#
# See the Postfix UUCP_README file for configuration details.
#
uucp      unix  -       n       n       -       -       pipe
  flags=Fqhu user=uucp argv=uux -r -n -z -a$sender - $nexthop!rmail ($recipient)
#
# Other external delivery methods.
#
ifmail    unix  -       n       n       -       -       pipe
  flags=F user=ftn argv=/usr/lib/ifmail/ifmail -r $nexthop ($recipient)
bsmtp     unix  -       n       n       -       -       pipe
  flags=Fq. user=bsmtp argv=/usr/lib/bsmtp/bsmtp -t$nexthop -f$sender $recipient
scalemail-backend unix  -       n       n       -       2       pipe
  flags=R user=scalemail argv=/usr/lib/scalemail/bin/scalemail-store ${nexthop} 
${user} ${extension}
mailman   unix  -       n       n       -       -       pipe
  flags=FR user=list argv=/usr/lib/mailman/bin/postfix-to-mailman.py
  ${nexthop} ${user}

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