O relé OpenSMTPd pessoal falha ao usar "tls-require", funciona bem apenas com "tls"

O relé OpenSMTPd pessoal falha ao usar "tls-require", funciona bem apenas com "tls"

Atualmente estou configurando um servidor de e-mail pessoal exclusivo usando OpenSMTPd. Tenho um servidor local (Raspberry Pi) e um servidor remoto (VPS). Os e-mails enviados para mim são enviados para o servidor remoto e então retransmitidos para o meu servidor local. Quando envio um e-mail, ele vai do servidor local para o servidor remoto e é retransmitido ao destinatário. Atualmente estou testando apenas e-mails recebidos e funciona principalmente, com apenas um problema, tls.

Se eu tiver "tls-require" definido em meu servidor local, meus servidores remotos parecem conseguir se conectar, mas depois se desconectam e tentam fazer o downgrade para simples (smtp + notls), o que obviamente falha. Se eu usar apenas "tls" em vez de "tls-require", a mesma coisa acontece, mas a tentativa smtp+notls funciona.

As mensagens de erro não parecem tão úteis. No servidor remoto, recebo "Falha no TLS oportunista, fazendo downgrade para simples". Como eu disse antes, no servidor local parece que a conexão FOI bem-sucedida (pelo menos acho que sim), mas depois desconecta:

smtp connected address=redacted.remote.ip.address host=mx1.mydomain.tld
smtp tls ciphers=TLSv1.3:TLS_AES_256_GCM_SHA384:256
smtp disconnected reason=disconnect

Recebo uma mensagem de erro um pouco mais informativa se tento enviar o email usando o openssl (do servidor remoto).

openssl s_client -debug -starttls smtp -crlf -connect redacted.local.ip.address:25

No servidor remoto tudo corre bem até eu inserir um destinatário, momento em que recebo um erro de SSL:

RCPT TO:<[email protected]>
RENEGOTIATING
17412933263728:error:1404C042:SSL routines:ST_OK:called a function you should not call:/usr/src/lib/libssl/ssl_lib.c:2529:

Esse erro parece me dizer mais, mas não consigo encontrar nada relevante sobre isso. O servidor local mostra exatamente o mesmo erro de antes.


Eu sei que muitas pessoas não usam TLS imposto com e-mail, mas para este caso de uso eu realmente gostaria que funcionasse.

Meu servidor local está executando "Raspberry Pi OS 11 bullseye 64 bits" e OpenSMTPD 6.8.0p2 (a versão mais recente no apt).

Meu servidor remoto está executando "OpenBSD 7.0 GENERIC#224 amd64" e OpenSMTPD 7.0.0.

Qualquer conselho seria muito apreciado. Por favor, deixe-me saber se você precisar de mais informações.


Aqui estão minhas configurações:

SERVIDOR LOCAL smtpd.conf:

table aliases "/etc/smtpd/aliases"
table domains "/etc/smtpd/domains"
table passwds "/etc/smtpd/passwds"
table remote-servers "/etc/smtpd/remote-servers"

pki "mydomain.tld" cert "/etc/letsencrypt/live/mydomain.tld/fullchain.pem"
pki "mydomain.tld" key "/etc/letsencrypt/live/mydomain.tld/privkey.pem"

# Do I want srs here, on the remote, or both?
srs key "redacted key"

filter   "rdns" phase connect match   !rdns disconnect "550 DNS error"
filter "fcrdns" phase connect match !fcrdns disconnect "550 DNS error"
filter "rspamd" proc-exec "/etc/smtpd/filter-rspamd"

# Inbound
listen on eth0 port 25 tls-require pki "mydomain.tld" filter { "rdns", "fcrdns" "rspamd" }
#listen on eth0 port 25 tls pki "mydomain.tld" filter { "rdns", "fcrdns" "rspamd" }
action "RECV" lmtp "/var/run/dovecot/lmtp" rcpt-to virtual <aliases>
match from src <remote-servers> for domain <domains> action "RECV"
match !from src <remote-servers> for domain <domains> reject

# Outbound
listen on eth0 port 465 smtps       pki "mydomain.tld" auth <passwds> filter "rspamd" mask-src
listen on eth0 port 587 tls-require pki "mydomain.tld" auth <passwds> filter "rspamd" mask-src
action "SEND" relay host mx1.mydomain.tld:465
match from any auth for any action "SEND"

SERVIDOR REMOTO smtpd.conf:

table aliases "/etc/smtpd/aliases"
table domains "/etc/smtpd/domains"

pki "mydomain.tld" cert "/etc/letsencrypt/live/mydomain.tld/fullchain.pem"
pki "mydomain.tld" key "/etc/letsencrypt/live/mydomain.tld/privkey.pem"

# Do I want srs here, on the remote, or both?
srs key "same redacted key"

filter   "rdns" phase connect match   !rdns disconnect "550 DNS error"
filter "fcrdns" phase connect match !fcrdns disconnect "550 DNS error"

# Inbound
listen on eth0 port 25 tls pki "mydomain.tld" filter { "rdns", "fcrdns" }
action "RECV" relay host redacted.local.ip.address:25
match from any for domain <domains> action "RECV"

# Outbound
listen on eth0 port 465 smtps pki "mydomain.tld" mask-src
action "SEND" relay srs
match from src redacted.local.ip.address for any action "SEND"
match !from src redacted.local.ip.address for any reject

Aqui estão os maillogs, se eu tiver"tls-exige"definir:

Log de correio do SERVIDOR LOCAL:

Apr  3 11:57:26 LocalHostname smtpd[3614276]: 3c3d3943d2bc7134 smtp connected address=redacted.remote.ip.address host=mx1.mydomain.tld
Apr  3 11:57:26 LocalHostname smtpd[3614276]: 3c3d3943d2bc7134 smtp tls ciphers=TLSv1.3:TLS_AES_256_GCM_SHA384:256
Apr  3 11:57:26 LocalHostname smtpd[3614276]: 3c3d3943d2bc7134 smtp disconnected reason=disconnect
Apr  3 11:57:26 LocalHostname smtpd[3614276]: 3c3d39441db05cc1 smtp connected address=redacted.remote.ip.address host=mx1.mydomain.tld
Apr  3 11:57:26 LocalHostname smtpd[3614276]: 3c3d39441db05cc1 smtp failed-command command="MAIL FROM:<[email protected]>" result="530 5.5.1 Invalid command: Must issue a STARTTLS command first"
Apr  3 11:57:43 LocalHostname smtpd[3614276]: 3c3d39441db05cc1 smtp disconnected reason=quit

Log de correio do SERVIDOR REMOTO:

Apr  3 11:57:19 RemoteHostname smtpd[94758]: 7349563019b45aeb smtp connected address=209.85.128.178 host=mail-yw1-f178.google.com
Apr  3 11:57:19 RemoteHostname smtpd[94758]: 7349563019b45aeb smtp tls ciphers=TLSv1.3:AEAD-AES256-GCM-SHA384:256
Apr  3 11:57:20 RemoteHostname smtpd[94758]: 7349563019b45aeb smtp message msgid=f8226363 size=2682 nrcpt=1 proto=ESMTP
Apr  3 11:57:20 RemoteHostname smtpd[94758]: 7349563019b45aeb smtp envelope evpid=f822636342a8821f from=<[email protected]> to=<[email protected]>
Apr  3 11:57:20 RemoteHostname smtpd[94758]: 734956336de69e03 mta connecting address=smtp://redacted.local.ip.address:25 host=redacted-local-ip-address.isp.tld
Apr  3 11:57:20 RemoteHostname smtpd[94758]: 734956336de69e03 mta connected
Apr  3 11:57:20 RemoteHostname smtpd[94758]: 7349563019b45aeb smtp disconnected reason=quit
Apr  3 11:57:20 RemoteHostname smtpd[94758]: smtp-out: Error on session 734956336de69e03: opportunistic TLS failed, downgrading to plain
Apr  3 11:57:20 RemoteHostname smtpd[94758]: 734956336de69e03 mta connecting address=smtp+notls://redacted.local.ip.address:25 host=redacted-local-ip-address.isp.tld
Apr  3 11:57:20 RemoteHostname smtpd[94758]: 734956336de69e03 mta connected
Apr  3 11:57:20 RemoteHostname smtpd[94758]: 734956336de69e03 mta delivery evpid=f822636342a8821f from=<[email protected]> to=<[email protected]> rcpt=<-> source="redacted.remote.ip.address" relay="redacted.local.ip.address (redacted-local-ip-address.isp.tld)" delay=1s result="PermFail" stat="530 5.5.1 Invalid command: Must issue a STARTTLS command first"
Apr  3 11:57:22 RemoteHostname smtpd[94758]: 73495634e55adfe9 smtp connected address=local host=mx1.mydomain.tld
Apr  3 11:57:22 RemoteHostname smtpd[94758]: 73495634e55adfe9 smtp failed-command command="RCPT TO: <[email protected]>" result="550 Invalid recipient: <[email protected]>"
Apr  3 11:57:22 RemoteHostname smtpd[11238]: warn: PermFail injecting failure report on message f8226363 to <[email protected]> for 1 envelope: 550 Invalid recipient: <[email protected]>
Apr  3 11:57:22 RemoteHostname smtpd[94758]: 73495634e55adfe9 smtp disconnected reason=quit
Apr  3 11:57:37 RemoteHostname smtpd[94758]: 734956336de69e03 mta disconnected reason=quit messages=0

E estes são os maillogs se eu tiver"tl"definir:

Log de correio do SERVIDOR LOCAL:

Apr  3 12:07:09 LocalHostname smtpd[3849290]: b981307e92d2eeac smtp connected address=redacted.remote.ip.address host=mx1.mydomain.tld
Apr  3 12:07:09 LocalHostname smtpd[3849290]: b981307e92d2eeac smtp tls ciphers=TLSv1.3:TLS_AES_256_GCM_SHA384:256
Apr  3 12:07:09 LocalHostname smtpd[3849290]: b981307e92d2eeac smtp disconnected reason=disconnect
Apr  3 12:07:09 LocalHostname smtpd[3849290]: b981307ff6e18ae3 smtp connected address=redacted.remote.ip.address host=mx1.mydomain.tld
Apr  3 12:07:10 LocalHostname smtpd[3849290]: b981307ff6e18ae3 smtp message msgid=082c7a5e size=2850 nrcpt=1 proto=ESMTP
Apr  3 12:07:10 LocalHostname smtpd[3849290]: b981307ff6e18ae3 smtp envelope evpid=082c7a5e9dec905f from=<[email protected]> to=<[email protected]>
Apr  3 12:07:11 LocalHostname dovecot: lmtp(3967460): Connect from local
Apr  3 12:07:11 LocalHostname dovecot: lmtp([email protected])<3967460><hmVpIN9/SWLkiTwAmV7YnQ>: msgid=<CACebY1Hm4jdhjFKoZ2374zbEq1MZV-yTxsUauV4gzxXqNBVeaQ@mail.gmail.com>: saved mail to INBOX
Apr  3 12:07:11 LocalHostname dovecot: lmtp(3967460): Disconnect from local: Client has quit the connection (state=READY)
Apr  3 12:07:11 LocalHostname smtpd[3849290]: b981308066da2115 mda delivery evpid=082c7a5e9dec905f from=<[email protected]> to=<[email protected]> rcpt=<[email protected]> user=vmail delay=2s result=Ok stat=Delivered
Apr  3 12:07:27 LocalHostname smtpd[3849290]: b981307ff6e18ae3 smtp disconnected reason=quit

Log de correio do SERVIDOR REMOTO:

Apr  3 12:06:59 RemoteHostname smtpd[94758]: 73495635c8c7456b smtp connected address=209.85.219.174 host=mail-yb1-f174.google.com
Apr  3 12:06:59 RemoteHostname smtpd[94758]: 73495635c8c7456b smtp tls ciphers=TLSv1.3:AEAD-AES256-GCM-SHA384:256
Apr  3 12:07:00 RemoteHostname smtpd[94758]: 73495635c8c7456b smtp message msgid=b912e335 size=2670 nrcpt=1 proto=ESMTP
Apr  3 12:07:00 RemoteHostname smtpd[94758]: 73495635c8c7456b smtp envelope evpid=b912e33501250790 from=<[email protected]> to=<[email protected]>
Apr  3 12:07:00 RemoteHostname smtpd[94758]: 7349563834c66e1a mta connecting address=smtp://redacted.local.ip.address:25 host=redacted-local-ip-address.isp.tld
Apr  3 12:07:00 RemoteHostname smtpd[94758]: 7349563834c66e1a mta connected
Apr  3 12:07:00 RemoteHostname smtpd[94758]: 73495635c8c7456b smtp disconnected reason=quit
Apr  3 12:07:00 RemoteHostname smtpd[94758]: smtp-out: Error on session 7349563834c66e1a: opportunistic TLS failed, downgrading to plain
Apr  3 12:07:00 RemoteHostname smtpd[94758]: 7349563834c66e1a mta connecting address=smtp+notls://redacted.local.ip.address:25 host=redacted-local-ip-address.isp.tld
Apr  3 12:07:00 RemoteHostname smtpd[94758]: 7349563834c66e1a mta connected
Apr  3 12:07:02 RemoteHostname smtpd[94758]: 7349563834c66e1a mta delivery evpid=b912e33501250790 from=<[email protected]> to=<[email protected]> rcpt=<-> source="redacted.remote.ip.address" relay="redacted.local.ip.address (redacted-local-ip-address.isp.tld)" delay=2s result="Ok" stat="250 2.0.0 082c7a5e Message accepted for delivery"
Apr  3 12:07:19 RemoteHostname smtpd[94758]: 7349563834c66e1a mta disconnected reason=quit messages=1

SERVIDOR REMOTO pf.conf:

#       $OpenBSD: pf.conf,v 1.55 2017/12/03 20:40:04 sthen Exp $
#
# See pf.conf(5) and /etc/examples/pf.conf

set skip on lo

block return    # block stateless traffic
pass            # establish keep-state

# By default, do not permit remote connections to X11
block return in on ! lo0 proto tcp to port 6000:6010

# Port build user does not need network
block return out log proto {tcp udp} user _pbuild

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