Michael W. Lucas via Postfix-users:
> Hi,
> 
> Running 3.8 on FreeBSD 14, with postfixadmin 3.4.
> 
> I'm trying to send a message and got this bounce message.
> 
> <gid...@secluded.site>: host mx.nixnet.email[5.161.67.119] said: 530 5.7.0
> Must issue a STARTTLS command first (in reply to MAIL FROM command)
> 
> 
> The default maillog is not any more helpful.
> 
> Feb 15 14:52:05 mail postfix/smtp[71197]: 3C900C012: 
> to=<gid...@secluded.site>, relay=mx.
> nixnet.email[5.161.67.119]:25, delay=0.56, delays=0.12/0.01/0.37/0.06, 
> dsn=5.7.0, status=
> bounced (host mx.nixnet.email[5.161.67.119] said: 530 5.7.0 Must issue a 
> STARTTLS command first (in reply to MAIL FROM command))
> 
> It seems to be saying that I'm not even trying STARTTLS?  My
> understanding was that smtpd_tls_security_level=may would enable

That is for RECEIVING mail. Use smtp_tls_security_level
fdor SENDING mail.

        Wietse

> opportunistic STARTTLS if present, but that doesn't seem to be
> happening? Out-of-band communication with the other site shows I
> disconnect and immediately hang up.
> 
> Any suggestions on how to debug this? postfinger and debug log
> below. (I *think* the debug log includes only this session, but tried
> to err on the side of including stuff.)
> 
> Thanks,
> ==ml
> 
> 
> postfinger - postfix configuration on Thu Feb 15 18:18:02 EST 2024
> version: 1.30
> 
> Warning: postfinger output may show private configuration information,
> such as ip addresses and/or domain names which you do not want to show
> to the public.  If this is the case it is your responsibility to modify
> the output to hide this private information.  [Remove this warning with
> the --nowarn option.]
> 
> --System Parameters--
> mail_version = 3.8.4
> hostname = mail.ratoperatedvehicle.com
> uname = FreeBSD mail.ratoperatedvehicle.com 14.0-RELEASE-p5 FreeBSD 
> 14.0-RELEASE-p5 #0: Tue Feb 13 23:37:36 UTC 2024     
> r...@amd64-builder.daemonology.net:/usr/obj/usr/src/amd64.amd64/sys/GENERIC 
> amd64
> 
> --Packaging information--
> 
> --main.cf non-default parameters--
> compatibility_level = 3.7
> debug_peer_list = 5.161.67.119
> debugger_command = PATH=/bin:/usr/bin:/usr/local/bin:/usr/X11R6/bin ddd 
> $daemon_directory/$process_name $process_id & sleep 5
> home_mailbox = Maildir/
> mailbox_command = /usr/local/libexec/dovecot/dovecot-lda -f "$SENDER" -a 
> "$RECIPIENT"
> mynetworks = hash:/etc/postfix/relay-clients.cidr
> postscreen_access_list = permit_mynetworks, 
> cidr:/etc/postfix/postscreen_spf_allowlist.cidr
> postscreen_bare_newline_enable = yes
> postscreen_dnsbl_action = drop
> postscreen_dnsbl_sites = zen.spamhaus.org*2 all.spamrats.com dnsbl.sorbs.net
> postscreen_dnsbl_threshold = 2
> postscreen_forbidden_commands = yes
> postscreen_greet_action = drop
> postscreen_pipelining_enable = yes
> smtp_tls_CApath = /etc/ssl/certs
> smtpd_sasl_auth_enable = yes
> smtpd_sasl_local_domain = $myhostname
> smtpd_sasl_path = private/dovecot-sasl
> smtpd_sender_login_maps = $virtual_alias_maps
> smtpd_sender_restrictions = hash:/etc/postfix/bad-domains
> smtpd_tls_chain_files = /etc/certs/mail.ratoperatedvehicle.com/privkey.pem, 
> /etc/certs/mail.ratoperatedvehicle.com/fullchain.pem
> smtpd_tls_ciphers = high
> smtpd_tls_mandatory_ciphers = high
> smtpd_tls_mandatory_protocols = $smtpd_tls_protocols
> smtpd_tls_protocols = >=TLSv1.2
> smtpd_tls_security_level = may
> transport_maps = hash:/etc/postfix/transport
> virtual_alias_maps = 
> proxy:mysql:/etc/postfix/sql/mysql_virtual_alias_maps.cf, 
> proxy:mysql:/etc/postfix/sql/mysql_virtual_alias_domain_maps.cf, 
> proxy:mysql:/etc/postfix/sql/mysql_virtual_alias_domain_catchall_maps.cf
> virtual_gid_maps = static:5000
> virtual_mailbox_base = /vhosts
> virtual_mailbox_domains = 
> proxy:mysql:/etc/postfix/sql/mysql_virtual_domains_maps.cf
> virtual_mailbox_maps = 
> proxy:mysql:/etc/postfix/sql/mysql_virtual_mailbox_maps.cf, 
> proxy:mysql:/etc/postfix/sql/mysql_virtual_alias_domain_mailbox_maps.cf
> virtual_minimum_uid = 1000
> virtual_transport = lmtp:unix:private/dovecot-lmtp
> virtual_uid_maps = static:5000
> 
> --master.cf--
> smtp      inet  n       -       n       -       1       postscreen
> smtpd     pass  -       -       n       -       -       smtpd
>   -o 
> smtpd_milters=unix:/var/run/pyspf-milter/pyspf-milter.sock,unix:/var/run/opendkim/opendkim.sock,inet:localhost:11332
> dnsblog   unix  -       -       n       -       0       dnsblog
> tlsproxy  unix  -       -       n       -       0       tlsproxy
> pickup    unix  n       -       n       60      1       pickup
> 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
> submission inet n - n - - smtpd
>   -o smtpd_tls_security_level=encrypt
>   -o smtpd_sasl_auth_enable=yes
>   -o 
> smtpd_client_restrictions=permit_mynetworks,permit_sasl_authenticated,reject
>   -o smtpd_sender_restrictions=reject_sender_login_mismatch
>   -o 
> smtpd_recipient_restrictions=reject_non_fqdn_recipient,reject_unknown_recipient_domain,permit_sasl_authenticated,reject
>   -o smtpd_milters=unix:/var/run/opendkim/opendkim.sock
> trickle    unix - - n - - smtp
>   -o syslog_name=postfix-trickle
>   -o trickle_destination_concurrency_limit=1
>   -o trickle_destination_rate_delay=1m
>   -o trickle_destination_recipient_limit=5
>   -o trickle_destination_concurrency_failed_cohort_limit=10
> 
> -- end of postfinger output --
> 
> 
> debug_peer log:
> 
> Feb 15 18:14:53 mail postfix/qmgr[45613]: 49EC181FB: from=<m...@mwl.io>, 
> size=817, nrcpt=1 (queue active)
> Feb 15 18:14:53 mail postfix/smtp[52971]: smtp_stream_setup: maxtime=300 
> enable_deadline=0 min_data_rate=0
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 220 mx.nixnet.email ESMTP Postfix (Debian/GNU)
> Feb 15 18:14:53 mail postfix/smtp[52971]: > mx.nixnet.email[5.161.67.119]:25: 
> EHLO mail.ratoperatedvehicle.com
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 250-mx.nixnet.email
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 250-PIPELINING
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 250-SIZE 10240000
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 250-VRFY
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 250-ETRN
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 250-STARTTLS
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 250-ENHANCEDSTATUSCODES
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 250-8BITMIME
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 250-DSN
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 250-SMTPUTF8
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 250 CHUNKING
> Feb 15 18:14:53 mail postfix/smtp[52971]: server features: 0x20901f size 
> 10240000
> Feb 15 18:14:53 mail postfix/smtp[52971]: Using ESMTP PIPELINING, TCP send 
> buffer size is 33580, PIPELINING buffer size is 4096
> Feb 15 18:14:53 mail postfix/smtp[52971]: smtp_stream_setup: maxtime=300 
> enable_deadline=0 min_data_rate=0
> Feb 15 18:14:53 mail postfix/smtp[52971]: > mx.nixnet.email[5.161.67.119]:25: 
> MAIL FROM:<m...@mwl.io> SIZE=817
> Feb 15 18:14:53 mail postfix/smtp[52971]: > mx.nixnet.email[5.161.67.119]:25: 
> RCPT TO:<gid...@secluded.site> ORCPT=rfc822;gid...@secluded.site
> Feb 15 18:14:53 mail postfix/smtp[52971]: > mx.nixnet.email[5.161.67.119]:25: 
> DATA
> Feb 15 18:14:53 mail postfix/smtp[52971]: smtp_stream_setup: maxtime=300 
> enable_deadline=0 min_data_rate=0
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 530 5.7.0 Must issue a STARTTLS command first
> Feb 15 18:14:53 mail postfix/smtp[52971]: connect to subsystem private/bounce
> Feb 15 18:14:53 mail postfix/smtp[52971]: private/bounce socket: wanted 
> attribute: protocol
> Feb 15 18:14:53 mail postfix/smtp[52971]: input attribute name: protocol
> Feb 15 18:14:53 mail postfix/smtp[52971]: input attribute value: 
> delivery_status_protocol
> Feb 15 18:14:53 mail postfix/smtp[52971]: private/bounce socket: wanted 
> attribute: (list terminator)
> Feb 15 18:14:53 mail postfix/smtp[52971]: input attribute name: (end)
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr nrequest = 0
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr flags = 0
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr queue_id = 49EC181FB
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr original_recipient = 
> gid...@secluded.site
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr recipient = 
> gid...@secluded.site
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr offset = 915
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr dsn_orig_rcpt = 
> rfc822;gid...@secluded.site
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr notify_flags = 0
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr status = 5.7.0
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr diag_type = smtp
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr diag_text = 530 5.7.0 
> Must issue a STARTTLS command first
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr mta_type = dns
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr mta_mname = 
> mx.nixnet.email
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr action = failed
> Feb 15 18:14:53 mail postfix/smtp[52971]: send attr reason = host 
> mx.nixnet.email[5.161.67.119] said: 530 5.7.0 Must issue a STARTTLS command 
> first (in reply to MAIL FROM command)
> Feb 15 18:14:53 mail postfix/smtp[52971]: private/bounce socket: wanted 
> attribute: status
> Feb 15 18:14:53 mail postfix/smtp[52971]: input attribute name: status
> Feb 15 18:14:53 mail postfix/smtp[52971]: input attribute value: 0
> Feb 15 18:14:53 mail postfix/smtp[52971]: private/bounce socket: wanted 
> attribute: (list terminator)
> Feb 15 18:14:53 mail postfix/smtp[52971]: input attribute name: (end)
> Feb 15 18:14:53 mail postfix/smtp[52971]: 49EC181FB: 
> to=<gid...@secluded.site>, relay=mx.nixnet.email[5.161.67.119]:25, 
> delay=0.44, delays=0.09/0.01/0.28/0.06, dsn=5.7.0, status=bounced (host 
> mx.nixnet.email[5.161.67.119] said: 530 5.7.0 Must issue a STARTTLS command 
> first (in reply to MAIL FROM command))
> Feb 15 18:14:53 mail postfix/smtp[52971]: smtp_stream_setup: maxtime=300 
> enable_deadline=0 min_data_rate=0
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 530 5.7.0 Must issue a STARTTLS command first
> Feb 15 18:14:53 mail postfix/smtp[52971]: smtp_stream_setup: maxtime=120 
> enable_deadline=0 min_data_rate=0
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 530 5.7.0 Must issue a STARTTLS command first
> Feb 15 18:14:53 mail postfix/smtp[52971]: > mx.nixnet.email[5.161.67.119]:25: 
> RSET
> Feb 15 18:14:53 mail postfix/smtp[52971]: > mx.nixnet.email[5.161.67.119]:25: 
> QUIT
> Feb 15 18:14:53 mail postfix/smtp[52971]: smtp_stream_setup: maxtime=20 
> enable_deadline=0 min_data_rate=0
> Feb 15 18:14:53 mail postfix/smtp[52971]: < mx.nixnet.email[5.161.67.119]:25: 
> 530 5.7.0 Must issue a STARTTLS command first
> Feb 15 18:14:53 mail postfix/smtp[52971]: name_mask: resource
> Feb 15 18:14:53 mail postfix/smtp[52971]: name_mask: software
> Feb 15 18:14:53 mail postfix/cleanup[52642]: C36BC83C1: 
> message-id=<20240215231453.c36bc8...@mail.ratoperatedvehicle.com>
> Feb 15 18:14:53 mail postfix/bounce[53616]: 49EC181FB: sender non-delivery 
> notification: C36BC83C1
> Feb 15 18:14:53 mail postfix/qmgr[45613]: C36BC83C1: from=<>, size=3416, 
> nrcpt=1 (queue active)
> Feb 15 18:14:53 mail postfix/qmgr[45613]: 49EC181FB: removed
> 
> 
> 
> 
> 
> 
> -- 
> Michael W. Lucas        https://mwl.io/
> author of: Absolute OpenBSD, SSH Mastery, git commit murder,
>  Absolute FreeBSD, Butterfly Stomp Waltz, TLS Mastery, etc...
> ### New books: DNSSEC Mastery, Letters to ed(1), $ git sync murder ###
> _______________________________________________
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> To unsubscribe send an email to postfix-users-le...@postfix.org
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