Postfix TLS issues

Nebhead · Jul 5, 2016

Hi all,
I tried installing a third party security certificate using the guide at https://www.howtoforge.com/securing...h-a-free-class1-ssl-certificate-from-startssl

I am now experiencing issues with my email. I can connect to the mailbox via IMAP using TLS (port 143), but when I try and send email I get the following error (from Outlook) when using TLS:
* On port 465 - "The connection to the server was interrupted"
* On port 25 - "Establishing an encrypted connection to your outgoing (SMTP) server failed"

I'm at a bit of a loss as to how to resolve this as my postfix conf appears okay:

/etc/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
submission inet n - - - - smtpd
-o smtpd_tls_security_level=encrypt
-o smtpd_sasl_auth_enable=yes
-o smtpd_client_restrictions=permit_sasl_authenticated,permit_mynetworks,check_relay_domains,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 vmail ${extension} ${recipient} ${user} ${nexthop} ${sender}
#
# ====================================================================
#
# 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}

amavis unix - - - - 2 smtp
-o smtp_data_done_timeout=1200
-o smtp_send_xforward_command=yes

127.0.0.1:10025 inet n - - - - smtpd
-o content_filter=
-o local_recipient_maps=
-o relay_recipient_maps=
-o smtpd_restriction_classes=
-o smtpd_client_restrictions=
-o smtpd_helo_restrictions=
-o smtpd_sender_restrictions=
-o smtpd_recipient_restrictions=permit_mynetworks,reject
-o mynetworks=127.0.0.0/8
-o strict_rfc821_envelopes=yes
-o receive_override_options=no_unknown_recipient_checks,no_header_body_checks
-o smtpd_bind_address=127.0.0.1
Click to expand...

/etc/postfix/main.cf

# 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 (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/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 = hades.nebhead.com
alias_maps = hash:/etc/aliases, hash:/var/lib/mailman/data/aliases
alias_database = hash:/etc/aliases, hash:/var/lib/mailman/data/aliases
myorigin = /etc/mailname
mydestination = hades.nebhead.com, localhost, localhost.localdomain
relayhost =
mynetworks = 127.0.0.0/8 [::1]/128
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
html_directory = /usr/share/doc/postfix/html
virtual_alias_domains =
virtual_alias_maps = hash:/var/lib/mailman/data/virtual-mailman, proxy:mysql:/etc/postfix/mysql-virtual_forwardings.cf, proxy: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 = /var/vmail
virtual_uid_maps = static:5000
virtual_gid_maps = static:5000
smtpd_sasl_auth_enable = yes
smtpd_sasl_security_options = noanonymous
smtpd_sasl_local_domain = $myhostname
smtpd_sasl_application_name = smtpd
broken_sasl_auth_clients = yes
smtpd_sasl_authenticated_header = yes
smtpd_recipient_restrictions = permit_mynetworks, permit_sasl_authenticated, check_relay_domains, reject_unauth_destination, check_recipient_access mysql:/etc/postfix/mysql-virtual_recipient.cf
smtpd_tls_security_level = may
transport_maps = hash:/var/lib/mailman/data/transport-mailman, proxy:mysql:/etc/postfix/mysql-virtual_transports.cf
relay_domains = mysql:/etc/postfix/mysql-virtual_relaydomains.cf
relay_recipient_maps = mysql:/etc/postfix/mysql-virtual_relayrecipientmaps.cf
virtual_create_maildirsize = yes
virtual_maildir_extended = yes
virtual_mailbox_limit_maps = proxy:mysql:/etc/postfix/mysql-virtual_mailbox_limit_maps.cf
virtual_mailbox_limit_override = yes
virtual_maildir_limit_message = "The user you are trying to reach is over quota."
virtual_overquota_bounce = 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
smtpd_sender_restrictions = check_sender_access mysql:/etc/postfix/mysql-virtual_sender.cf
smtpd_client_restrictions = check_client_access mysql:/etc/postfix/mysql-virtual_client.cf
maildrop_destination_concurrency_limit = 1
maildrop_destination_recipient_limit = 1
virtual_transport = maildrop
header_checks = regexp:/etc/postfix/header_checks
mime_header_checks = regexp:/etc/postfix/mime_header_checks
nested_header_checks = regexp:/etc/postfix/nested_header_checks
body_checks = regexp:/etc/postfix/body_checks
content_filter = amavis:[127.0.0.1]:10024
receive_override_options = no_address_mappings
message_size_limit = 0
smtpd_client_message_rate_limit = 100
owner_request_special = no
inet_protocols = all
smtp_tls_security_level = may
smtpd_tls_mandatory_protocols = !SSLv2, !SSLv3
smtpd_tls_protocols = !SSLv2,!SSLv3
smtp_tls_protocols = !SSLv2,!SSLv3
smtpd_tls_CAfile = /usr/local/ispconfig/interface/ssl/startssl.sub.class1.server.ca.crt
Click to expand...

Any and all help much appreciated.

Thanks,
Ben

Nebhead · Jul 15, 2016

... anyone?

sjau · Jul 16, 2016

what does server log say?
Also, I use LetsEncrypt certs for dovecot and postfix and wrote a little script to auto-renew those certs.

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Postfix TLS issues

Nebhead New Member

Nebhead New Member

sjau Local Meanie Moderator

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Postfix TLS issues

Nebhead New Member

Nebhead New Member

sjau Local Meanie Moderator

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