hi
i'm playing with a nas i've installed debian stable on, and i used to
have some scripts with mailx work to send me messages through external
providers/servers/etc till i upgraded debian: now i can't send mails
through mailx but i can through telnet and swaks: here are mailx and
swaks logs, please treat me as a true noob

echo “Subject: sendmail test” | mail -v [email protected]
LOG: MAIN
  <= [email protected] U=root P=local S=479
➜  ~ delivering 1mk3js-0006Jf-IB
R: smarthost for [email protected]
T: remote_smtp_smarthost for [email protected]
Connecting to mail.federcasapescara.it [185.4.142.93]:25 ...  TFO mode
sendto, no data: EINPROGRESS
 connected
  SMTP<< 220 directadmin30.fastnom.com ESMTP Exim 4.94.2 Mon, 08 Nov
2021 13:27:05 +0100
  SMTP>> EHLO ilmionasone.fritz.box
  SMTP<< 250-directadmin30.fastnom.com Hello
host-95-247-26-164.retail.telecomitalia.it [95.247.26.164]
         250-SIZE 52428800
         250-8BITMIME
         250-PIPELINING
         250-PIPE_CONNECT
         250-AUTH PLAIN LOGIN
         250-STARTTLS
         250 HELP
  SMTP>> STARTTLS
  SMTP<< 220 TLS go ahead
  SMTP(close)>>
LOG: MAIN
  TLS session: (certificate verification failed): delivering
unencrypted to H=mail.federcasapescara.it [185.4.142.93] (not in
hosts_require_tls)
Connecting to mail.federcasapescara.it [185.4.142.93]:25 ...  TFO mode
sendto, no data: EINPROGRESS
 connected
  SMTP<< 220 directadmin30.fastnom.com ESMTP Exim 4.94.2 Mon, 08 Nov
2021 13:27:05 +0100
  SMTP>> EHLO ilmionasone.fritz.box
  SMTP<< 250-directadmin30.fastnom.com Hello
host-95-247-26-164.retail.telecomitalia.it [95.247.26.164]
         250-SIZE 52428800
         250-8BITMIME
         250-PIPELINING
         250-PIPE_CONNECT
         250-AUTH PLAIN LOGIN
         250-STARTTLS
         250 HELP
  SMTP>> MAIL FROM:<[email protected]> SIZE=1515
  SMTP>> RCPT TO:<[email protected]>
  SMTP>> DATA
  SMTP<< 250 OK
  SMTP<< 550 authentication required
  SMTP<< 503-All RCPT commands were rejected with this error:
         503-authentication required
         503 Valid RCPT command must precede DATA
  SMTP>> QUIT
  SMTP(close)>>
LOG: MAIN
  ** [email protected] R=smarthost T=remote_smtp_smarthost
H=mail.federcasapescara.it [185.4.142.93]: SMTP error from remote mail
server after RCPT TO:<[email protected]>: 550 authentication
required
LOG: MAIN
  <= <> R=1mk3js-0006Jf-IB U=Debian-exim P=local S=2021
delivering 1mk3jv-0006Jl-Th
R: system_aliases for [email protected]
LOG: MAIN
  ** [email protected]: Unrouteable address
LOG: MAIN
  Frozen (delivery error message)
LOG: MAIN
  Completed



swaks --tls --auth --to [email protected] --server
mail.federcasapescara.it
Username: [email protected]
Password: xxx
=== Trying mail.federcasapescara.it:25...
=== Connected to mail.federcasapescara.it.
<-  220 directadmin30.fastnom.com ESMTP Exim 4.94.2 Mon, 08 Nov 2021
22:22:41 +0100
 -> EHLO ilmionasone.fritz.box
<-  250-directadmin30.fastnom.com Hello
host-95-247-26-164.retail.telecomitalia.it [95.247.26.164]
<-  250-SIZE 52428800
<-  250-8BITMIME
<-  250-PIPELINING
<-  250-PIPE_CONNECT
<-  250-AUTH PLAIN LOGIN
<-  250-STARTTLS
<-  250 HELP
 -> STARTTLS
<-  220 TLS go ahead
=== TLS started with cipher TLSv1.2:ECDHE-RSA-AES128-GCM-SHA256:128
=== TLS no local certificate set
=== TLS peer DN="/CN=directadmin30.fastnom.com"
 ~> EHLO ilmionasone.fritz.box
<~  250-directadmin30.fastnom.com Hello
host-95-247-26-164.retail.telecomitalia.it [95.247.26.164]
<~  250-SIZE 52428800
<~  250-8BITMIME
<~  250-PIPELINING
<~  250-PIPE_CONNECT
<~  250-AUTH PLAIN LOGIN
<~  250 HELP
 ~> AUTH LOGIN
<~  334 VXNlcm5hbWU6
 ~> bmFzb25lQGZlZGVyY2FzYXBlc2NhcmEuaXQ=
<~  334 UGFzc3dvcmQ6
 ~> Tmd1bGFtbWFtbXQxIQ==
<~  235 Authentication succeeded
 ~> MAIL FROM:<[email protected]>
<~  250 OK
 ~> RCPT TO:<[email protected]>
<~  250 Accepted
 ~> DATA
<~  354 Enter message, ending with "." on a line by itself
 ~> Date: Mon, 08 Nov 2021 22:21:39 +0100
 ~> To: [email protected]
 ~> From: [email protected]
 ~> Subject: test Mon, 08 Nov 2021 22:21:39 +0100
 ~> Message-Id: <[email protected]>
 ~> X-Mailer: swaks v20201014.0 jetmore.org/john/code/swaks/
 ~>
 ~> This is a test mailing
 ~>
 ~>
 ~> .
<~  250 OK id=1mkC6D-000Vj8-Sr
 ~> QUIT
<~  221 directadmin30.fastnom.com closing connection
=== Connection closed with remote host.

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