Your logs contain valid login and password. Also, note, that AUTH LOGIN (as 
well as AUTH PLAIN) is just base64, so password may be recovered in plain text.

# telnet mail.federcasapescara.it  25
Trying 185.4.142.93...
Connected to mail.federcasapescara.it.
Escape character is '^]'.
220 directadmin30.fastnom.com ESMTP Exim 4.94.2 Wed, 10 Nov 2021 12:17:45
+0100
EHLO test
250-directadmin30.fastnom.com Hello test [213.108.248.159]
250-SIZE 52428800
250-8BITMIME
250-PIPELINING
250-PIPE_CONNECT
250-AUTH PLAIN LOGIN
250-STARTTLS
250 HELP
AUTH LOGIN
334 VXNlcm5hbWU6
bmFzb25lQGZlZGVyY2FzYXBlc2NhcmEuaXQ=
334 UGFzc3dvcmQ6
Tmd1bGFtbWFtbXQxIQ==
235 Authentication succeeded

2021/11/10 11:20:15 Carlo via Exim-users <[email protected]>:

> 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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