SMTP not working on ubuntu 12.04, with postfix and dovecot 2

I followed the linode guide on setting up postfix and dovecot on ubuntu.

Both pop3 and IMAP are working.

I am having trouble with STMP. I am getting the following errors in /var/log/mail.log

Dec 21 18:38:03 pareto postfix/smtpd[17516]: SSL_accept:failed in SSLv3 read client certificate A
Dec 21 18:38:03 pareto postfix/smtpd[17516]: SSL_accept error from unknown[69.165.232.221]: lost connection
Dec 21 18:38:03 pareto postfix/smtpd[17516]: lost connection after STARTTLS from unknown[69.165.232.221]
Dec 21 18:38:03 pareto postfix/smtpd[17516]: disconnect from unknown[69.165.232.221]

I have been trying to fix this for 2 days now. No advance at all. If you have any idea on how to debug this please let me know.

Telnet output:

Trying 127.0.0.1...
Connected to localhost.
Escape character is '^]'.
220 pareto.qpapaya.com ESMTP Postfix (Ubuntu)
ehlo localhost
250-pareto.qpapaya.com
250-PIPELINING
250-SIZE 30720000
250-VRFY
250-ETRN
250-STARTTLS
250-AUTH PLAIN
250-AUTH=PLAIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN

Configuration files follow

My dovecot v2 configuration file, converted from v1 using doveconf -n -c /etc/dovecot/dovecot.conf > dovecot-2.conf http://wiki2.dovecot.org/Upgrading/2.0

# 2.0.19: /etc/dovecot/dovecot.conf
# OS: Linux 3.6.5-linode47 i686 Ubuntu 12.04.1 LTS ext3
log_timestamp = "%Y-%m-%d %H:%M:%S "
mail_location = maildir:/home/vmail/%d/%n/Maildir
managesieve_notify_capability = mailto
managesieve_sieve_capability = fileinto reject envelope encoded-character vacation subaddress comparator-i;ascii-numeric relational regex imap4flags copy include variables body enotify environment mailbox date ihave
namespace {
  inbox = yes
  location = 
  prefix = INBOX.
  separator = .
  type = private
}
passdb {
  args = /etc/dovecot/dovecot-sql.conf
  driver = sql
}
protocols = imap pop3
service auth {
  unix_listener /var/spool/postfix/private/auth {
    group = postfix
    mode = 0660
    user = postfix
  }
  unix_listener auth-master {
    mode = 0600
    user = vmail
  }
  user = root
}
ssl_cert = 

My postfix main.cf

# See /usr/share/postfix/main.cf.dist for a commented, more complete version

queue_directory = /var/spool/postfix

# 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 (Ubuntu)
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 = /usr/share/doc/postfix

# TLS parameters
#smtpd_tls_cert_file = /etc/ssl/certs/ssl-mail.pem
#smtpd_tls_key_file = /etc/ssl/private/ssl-mail.key
smtpd_tls_cert_file = /etc/postfix/smtpd.cert
smtpd_tls_key_file = /etc/postfix/smtpd.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 = pareto.qpapaya.com
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
myorigin = /etc/mailname
mydestination = pareto.qpapaya.com, localhost, localhost.localdomain
relayhost = 
mynetworks = 127.0.0.0/8
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
html_directory = /usr/share/doc/postfix/html
message_size_limit = 30720000
virtual_alias_domains = 
virtual_alias_maps = proxy:mysql:/etc/postfix/mysql-virtual_forwardings.cf, mysql:/etc/postfix/mysql-virtual_email2email.cf
virtual_mailbox_domains = proxy:mysql:/etc/postfix/mysql-virtual_domains.cf
virtual_mailbox_maps = proxy:mysql:/etc/postfix/mysql-virtual_mailboxes.cf
virtual_mailbox_base = /home/vmail
virtual_uid_maps = static:5000
virtual_gid_maps = static:5000
smtpd_sasl_auth_enable = yes
broken_sasl_auth_clients = yes
smtpd_sasl_authenticated_header = yes
#smtpd_recipient_restrictions = reject_unknown_sender_domain, reject_unknown_recipient_domain, reject_unauth_pipelining, permit_mynetworks, permit_sasl_authenticated, reject_unauth_destination
smtpd_recipient_restrictions = permit_mynetworks, permit_sasl_authenticated, reject_unauth_destination
virtual_create_maildirsize = yes
virtual_maildir_extended = yes
proxy_read_maps = $local_recipient_maps $mydestination $virtual_alias_maps $virtual_alias_domains $virtual_mailbox_maps $virtual_mailbox_domains $relay_recipient_maps $relay_domains $canonical_maps $sender_canonical_maps $recipient_canonical_maps $relocated_maps $transport_maps $mynetworks $virtual_mailbox_limit_maps
virtual_transport = dovecot
dovecot_destination_recipient_limit = 1
home_mailbox = Maildir/
smtpd_sasl_type = dovecot
#smtpd_sasl_path = private/dovecot-auth
#smtpd_sasl_path = /var/spool/postfix/dovecot-auth
smtpd_sasl_path = private/auth
smtpd_sasl_security_options = noanonymous
smtpd_sasl_local_domain = $myhostname
smtpd_sender_restrictions = reject_unknown_sender_domain
mailbox_command = /usr/lib/dovecot/deliver -c /etc/dovecot/conf.d/01-mail-stack-delivery.conf -m "${EXTENSION}"
smtp_use_tls = yes
smtpd_tls_received_header = yes
smtpd_tls_mandatory_protocols = SSLv3, TLSv1
smtpd_tls_mandatory_ciphers = medium
#smtpd_tls_auth_only = yes 
smtpd_tls_auth_only = no
tls_random_source = dev:/dev/urandom
smtpd_tls_loglevel = 4

My postfix master.cf

#
# 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
#smtp      inet  n       -       -       -       1       postscreen
#smtpd     pass  -       -       -       -       -       smtpd
#dnsblog   unix  -       -       -       -       0       dnsblog
#tlsproxy  unix  -       -       -       -       0       tlsproxy
#submission inet n       -       -       -       -       smtpd
#  -o syslog_name=postfix/submission
#  -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 syslog_name=postfix/smtps
#  -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       -       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
relay     unix  -       -       -       -       -       smtp
#       -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}
#
# ====================================================================
#
# Recent Cyrus versions can use the existing "lmtp" master.cf entry.
#
# Specify in cyrus.conf:
#   lmtp    cmd="lmtpd -a" listen="localhost:lmtp" proto=tcp4
#
# Specify in main.cf one or more of the following:
#  mailbox_transport = lmtp:inet:localhost
#  virtual_transport = lmtp:inet:localhost
#
# ====================================================================
#
# Cyrus 2.1.5 (Amos Gouaux)
# Also specify in main.cf: cyrus_destination_recipient_limit=1
#
#cyrus     unix  -       n       n       -       -       pipe
#  user=cyrus argv=/cyrus/bin/deliver -e -r ${sender} -m ${extension} ${user}
#
# ====================================================================
# Old example of delivery via Cyrus.
#
#old-cyrus unix  -       n       n       -       -       pipe
#  flags=R user=cyrus argv=/cyrus/bin/deliver -e -m ${extension} ${user}
#
# ====================================================================
#
# See the Postfix UUCP_README file for configuration details.
#
uucp      unix  -       n       n       -       -       pipe
  flags=Fqhu user=uucp argv=uux -r -n -z -a$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}

# http://library.linode.com/email/postfix/dovecot-mysql-ubuntu-10.04-lucid
dovecot   unix  -       n       n       -       -       pipe
    flags=DRhu user=vmail:vmail argv=/usr/lib/dovecot/deliver -d ${recipient}

1 Reply

It turns out that the problem was that Apple Mail doesn't like self signed certificates.

Used thunderbird and all works!

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