Hi Victor and Benny.

To answer your questions...

Victor...

*>>Test one thing at a time.  First get it working for interactive *connections
via $ (sleep 2; printf "QUIT\r\n") | openssl s_client -noservername -brief
-connect 127.0.0.1:465

I did this just now and all looks correct. I see the handshake.No errors.

*>>Once that works, proceed to testing Outlook, and looking at the Postfix
logs for relevant diagnostic messages.*

I tested Outlook and received an error in outlook which I have already
posted to this thread. As for Postfix, there is nothing at all showing in
the log for my test.

*>>You should start with:** 465     ine*t * n       -       n       -
 -       smtpd*

I tried the configuration you gave me and same thing..*. Outlook error,
nothing in the Postfix log.*


Benny....

* postconf -nf*

See attached.


* openssl --version *

OpenSSL 1.1.1f  31 Mar 2020


* postconf -Mf *

See attached.

*Windows 7 ? *

No, Windows 10 Pro

Thanks!


On Fri, Jun 11, 2021 at 11:13 AM Linda Pagillo <lpad...@gmail.com> wrote:

> Here is the Outlook error when testing using port 465 over SSL...
>
> [image: image.png]
> As for the Postfix log there is no entry for this test. It seems like the
> connection attempt is not even happening or something. However, the
> firewall does not seem to be the issue I don;t think.
>
>
>
> On Fri, Jun 11, 2021 at 10:45 AM Herbert J. Skuhra <herb...@gojira.at>
> wrote:
>
>> On Fri, Jun 11, 2021 at 10:32:38AM -0500, Linda Pagillo wrote:
>> >
>> > Thank you Herbert! I will give that a try. However... I'm trying to test
>> > connecting to port 465 over SSL from my Outlook mail client and it will
>> not
>> > connect. Any ideas why not? I can connect to 993 and 995 from Outlook.
>>
>> What error message do you get? What does postfix log?
>>
>> --
>> Herbert
>>
>
alias_database = hash:/etc/postfix/aliases
alias_maps = hash:/etc/postfix/aliases
allow_min_user = no
allow_percent_hack = no
biff = no
body_checks = pcre:/etc/postfix/body_checks.pcre
command_directory = /usr/sbin
compatibility_level = 2
content_filter = smtp-amavis:[127.0.0.1]:10024
daemon_directory = /usr/lib/postfix/sbin
data_directory = /var/lib/postfix
debug_peer_level = 2
debugger_command = PATH=/bin:/usr/bin:/usr/local/bin:/usr/X11R6/bin ddd
    $daemon_directory/$process_name $process_id & sleep 5
disable_vrfy_command = yes
dovecot_destination_recipient_limit = 1
enable_long_queue_ids = yes
enable_original_recipient = no
header_checks = pcre:/etc/postfix/header_checks
inet_interfaces = all
inet_protocols = all
lmtp_tls_mandatory_protocols = !SSLv2 !SSLv3
lmtp_tls_protocols = !SSLv2 !SSLv3
mail_owner = postfix
mailq_path = /usr/bin/mailq
message_size_limit = 15728640
mlmmj_destination_recipient_limit = 1
mydestination = $myhostname, localhost, localhost.localdomain
mydomain = 0.transportania.net
myhostname = 0.transportania.net
mynetworks = 127.0.0.1 [::1]
myorigin = 0.transportania.net
newaliases_path = /usr/bin/newaliases
postscreen_access_list = permit_mynetworks
    cidr:/etc/postfix/postscreen_access.cidr
postscreen_blacklist_action = drop
postscreen_dnsbl_action = drop
postscreen_dnsbl_reply_map = texthash:/etc/postfix/postscreen_dnsbl_reply
postscreen_dnsbl_sites = zen.spamhaus.org=127.0.0.[2..11]*3
    b.barracudacentral.org=127.0.0.2*2
postscreen_dnsbl_threshold = 2
postscreen_dnsbl_whitelist_threshold = -2
postscreen_greet_action = drop
proxy_read_maps = $canonical_maps $lmtp_generic_maps $local_recipient_maps
    $mydestination $mynetworks $recipient_bcc_maps $recipient_canonical_maps
    $relay_domains $relay_recipient_maps $relocated_maps $sender_bcc_maps
    $sender_canonical_maps $smtp_generic_maps $smtpd_sender_login_maps
    $transport_maps $virtual_alias_domains $virtual_alias_maps
    $virtual_mailbox_domains $virtual_mailbox_maps $smtpd_sender_restrictions
    $sender_dependent_relayhost_maps
queue_directory = /var/spool/postfix
recipient_bcc_maps = proxy:ldap:/etc/postfix/ldap/recipient_bcc_maps_user.cf
    proxy:ldap:/etc/postfix/ldap/recipient_bcc_maps_domain.cf
recipient_delimiter = +
relay_domains = $mydestination proxy:ldap:/etc/postfix/ldap/relay_domains.cf
sender_bcc_maps = proxy:ldap:/etc/postfix/ldap/sender_bcc_maps_user.cf
    proxy:ldap:/etc/postfix/ldap/sender_bcc_maps_domain.cf
sender_dependent_relayhost_maps =
    proxy:ldap:/etc/postfix/ldap/sender_dependent_relayhost_maps_user.cf
    proxy:ldap:/etc/postfix/ldap/sender_dependent_relayhost_maps_domain.cf
sendmail_path = /usr/sbin/sendmail
setgid_group = postdrop
show_user_unknown_table_name = no
smtp-amavis_destination_recipient_limit = 1
smtp_tls_CAfile = $smtpd_tls_CAfile
smtp_tls_CApath = /etc/ssl/certs
smtp_tls_loglevel = 1
smtp_tls_mandatory_protocols = !SSLv2 !SSLv3
smtp_tls_note_starttls_offer = yes
smtp_tls_protocols = !SSLv2 !SSLv3
smtp_tls_security_level = may
smtpd_command_filter = pcre:/etc/postfix/command_filter.pcre
smtpd_data_restrictions = reject_unauth_pipelining
smtpd_end_of_data_restrictions = check_policy_service inet:127.0.0.1:7777
smtpd_helo_required = yes
smtpd_helo_restrictions = permit_mynetworks permit_sasl_authenticated
    check_helo_access pcre:/etc/postfix/helo_access.pcre
    reject_non_fqdn_helo_hostname reject_unknown_helo_hostname
smtpd_recipient_restrictions = reject_non_fqdn_recipient
    reject_unlisted_recipient check_policy_service inet:127.0.0.1:7777
    permit_mynetworks permit_sasl_authenticated reject_unauth_destination
    check_policy_service inet:127.0.0.1:12340
smtpd_reject_unlisted_recipient = yes
smtpd_reject_unlisted_sender = yes
smtpd_sasl_path = private/dovecot-auth
smtpd_sasl_type = dovecot
smtpd_sender_login_maps = proxy:ldap:/etc/postfix/ldap/sender_login_maps.cf
smtpd_sender_restrictions = reject_non_fqdn_sender reject_unlisted_sender
    permit_mynetworks permit_sasl_authenticated check_sender_access
    pcre:/etc/postfix/sender_access.pcre reject_unknown_sender_domain
smtpd_tls_CApath = /etc/ssl/certs
smtpd_tls_chain_files = /etc/letsencrypt/live/0.transportania.net/privkey.pem,
    /etc/letsencrypt/live/0.transportania.net/fullchain.pem
smtpd_tls_dh1024_param_file = /etc/ssl/dh2048_param.pem
smtpd_tls_dh512_param_file = /etc/ssl/dh512_param.pem
smtpd_tls_exclude_ciphers = aNULL, eNULL, EXPORT, DES, RC4, MD5, PSK, aECDH,
    EDH-DSS-DES-CBC3-SHA, EDH-RSA-DES-CDC3-SHA, KRB5-DE5, CBC3-SHA
smtpd_tls_loglevel = 1
smtpd_tls_mandatory_protocols = !SSLv2 !SSLv3
smtpd_tls_protocols = !SSLv2 !SSLv3
smtpd_tls_security_level = may
swap_bangpath = no
tls_random_source = dev:/dev/urandom
tls_server_sni_maps = hash:/etc/postfix/vmail_ssl.map
transport_maps = proxy:ldap:/etc/postfix/ldap/transport_maps_user.cf
    proxy:ldap:/etc/postfix/ldap/transport_maps_domain.cf
unknown_local_recipient_reject_code = 550
virtual_alias_domains =
virtual_alias_maps = proxy:ldap:/etc/postfix/ldap/virtual_alias_maps.cf
    proxy:ldap:/etc/postfix/ldap/virtual_group_maps.cf
    proxy:ldap:/etc/postfix/ldap/virtual_group_members_maps.cf
    proxy:ldap:/etc/postfix/ldap/catchall_maps.cf
virtual_gid_maps = static:2000
virtual_mailbox_base = /var/vmail
virtual_mailbox_domains =
    proxy:ldap:/etc/postfix/ldap/virtual_mailbox_domains.cf
virtual_mailbox_maps = proxy:ldap:/etc/postfix/ldap/virtual_mailbox_maps.cf
virtual_minimum_uid = 2000
virtual_transport = dovecot
virtual_uid_maps = static:2000
smtp       inet  n       -       y       -       1       postscreen
smtpd      pass  -       -       y       -       -       smtpd
dnsblog    unix  -       -       y       -       0       dnsblog
tlsproxy   unix  -       -       y       -       0       tlsproxy
pickup     unix  n       -       n       60      1       pickup
    -o content_filter=smtp-amavis:[127.0.0.1]:10026
cleanup    unix  n       -       n       -       0       cleanup
qmgr       unix  n       -       n       300     1       qmgr
tlsmgr     unix  -       -       n       1000?   1       tlsmgr
rewrite    unix  -       -       n       -       -       trivial-rewrite
bounce     unix  -       -       n       -       0       bounce
defer      unix  -       -       n       -       0       bounce
trace      unix  -       -       n       -       0       bounce
verify     unix  -       -       n       -       1       verify
flush      unix  n       -       n       1000?   0       flush
proxymap   unix  -       -       n       -       -       proxymap
proxywrite unix  -       -       n       -       1       proxymap
smtp       unix  -       -       n       -       -       smtp
relay      unix  -       -       n       -       -       smtp
    -o syslog_name=postfix/$service_name
showq      unix  n       -       n       -       -       showq
error      unix  -       -       n       -       -       error
retry      unix  -       -       n       -       -       error
discard    unix  -       -       n       -       -       discard
local      unix  -       n       n       -       -       local
virtual    unix  -       n       n       -       -       virtual
lmtp       unix  -       -       n       -       -       lmtp
anvil      unix  -       -       n       -       1       anvil
scache     unix  -       -       n       -       1       scache
postlog    unix-dgram n  -       n       -       1       postlogd
maildrop   unix  -       n       n       -       -       pipe flags=DRhu
    user=vmail argv=/usr/bin/maildrop -d ${recipient}
uucp       unix  -       n       n       -       -       pipe flags=Fqhu
    user=uucp argv=uux -r -n -z -a$sender - $nexthop!rmail ($recipient)
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}
submission inet  n       -       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 content_filter=smtp-amavis:[127.0.0.1]:10026
dovecot    unix  -       n       n       -       -       pipe flags=DRh
    user=vmail:vmail argv=/usr/lib/dovecot/deliver -f ${sender} -d
    ${user}@${domain} -m ${extension}
mlmmj      unix  -       n       n       -       -       pipe flags=ORhu
    user=mlmmj:mlmmj argv=/usr/bin/mlmmj-amime-receive -L
    /var/vmail/mlmmj/${nexthop}
smtp-amavis unix -       -       n       -       4       smtp
    -o syslog_name=postfix/amavis
    -o smtp_data_done_timeout=1200
    -o smtp_send_xforward_command=yes
    -o disable_dns_lookups=yes
    -o max_use=20
127.0.0.1:10025 inet n   -       n       -       -       smtpd
    -o syslog_name=postfix/10025
    -o content_filter=
    -o mynetworks_style=host
    -o mynetworks=127.0.0.0/8
    -o local_recipient_maps=
    -o relay_recipient_maps=
    -o strict_rfc821_envelopes=yes
    -o smtp_tls_security_level=none
    -o smtpd_tls_security_level=none
    -o smtpd_restriction_classes=
    -o smtpd_delay_reject=no
    -o smtpd_client_restrictions=permit_mynetworks,reject
    -o smtpd_helo_restrictions=
    -o smtpd_sender_restrictions=
    -o smtpd_recipient_restrictions=permit_mynetworks,reject
    -o smtpd_end_of_data_restrictions=
    -o smtpd_error_sleep_time=0
    -o smtpd_soft_error_limit=1001
    -o smtpd_hard_error_limit=1000
    -o smtpd_client_connection_count_limit=0
    -o smtpd_client_connection_rate_limit=0
    -o 
receive_override_options=no_header_body_checks,no_unknown_recipient_checks,no_address_mappings
127.0.0.1:10028 inet n   -       n       -       -       smtpd
    -o syslog_name=postfix/10028
    -o content_filter=
    -o mynetworks_style=host
    -o mynetworks=127.0.0.0/8
    -o local_recipient_maps=
    -o relay_recipient_maps=
    -o strict_rfc821_envelopes=yes
    -o smtp_tls_security_level=none
    -o smtpd_tls_security_level=none
    -o smtpd_restriction_classes=
    -o smtpd_delay_reject=no
    -o smtpd_client_restrictions=permit_mynetworks,reject
    -o smtpd_helo_restrictions=
    -o smtpd_sender_restrictions=
    -o smtpd_recipient_restrictions=permit_mynetworks,reject
    -o smtpd_end_of_data_restrictions=
    -o smtpd_error_sleep_time=0
    -o smtpd_soft_error_limit=1001
    -o smtpd_hard_error_limit=1000
    -o smtpd_client_connection_count_limit=0
    -o smtpd_client_connection_rate_limit=0
    -o 
receive_override_options=no_header_body_checks,no_unknown_recipient_checks
465        inet  n       -       n       -       -       smtpd
    -o syslog_name=postfix/submissions
    -o smtpd_tls_wrappermode=yes
    -o smtpd_sasl_auth_enable=yes
    -o smtpd_reject_unlisted_recipient=no
    -o smtpd_client_restrictions=
    -o smtpd_helo_restrictions=
    -o smtpd_sender_restrictions=
    -o smtpd_relay_restrictions=
    -o smtpd_recipient_restrictions=permit_sasl_authenticated,reject
    -o milter_macro_daemon_name=ORIGINATING

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