jek@jeknote:~$ swaks --from info@hackerspace.by --to jekhor@gmail.com --auth PLAIN --auth-user info@hackerspace.by -s smtp.yandex.com -tls
Password: ****************
=== Trying smtp.yandex.com:25...
=== Connected to smtp.yandex.com.
<-  220 smtp1p.mail.yandex.net ESMTP (Want to use Yandex.Mail for your domain? Visit http://pdd.yandex.ru)
 -> EHLO localhost.localdomain
<-  250-smtp1p.mail.yandex.net
<-  250-8BITMIME
<-  250-PIPELINING
<-  250-SIZE 42991616
<-  250-STARTTLS
<-  250-AUTH LOGIN PLAIN XOAUTH2
<-  250-DSN
<-  250 ENHANCEDSTATUSCODES
 -> STARTTLS
<-  220 Go ahead
=== TLS started with cipher TLSv1.2:ECDHE-RSA-AES128-GCM-SHA256:128
=== TLS no local certificate set
=== TLS peer DN="/C=RU/O=Yandex LLC/OU=ITO/L=Moscow/ST=Russian Federation/CN=smtp.yandex.ru"
 ~> EHLO localhost.localdomain
<~  250-smtp1p.mail.yandex.net
<~  250-8BITMIME
<~  250-PIPELINING
<~  250-SIZE 42991616
<~  250-AUTH LOGIN PLAIN XOAUTH2
<~  250-DSN
<~  250 ENHANCEDSTATUSCODES
 ~> AUTH PLAIN AGluZm9AaGFja2Vyc3BhY2UuYnkAenV4ZnpsZnRmcGJmZGRqdQ==
<~  235 2.7.0 Authentication successful.
 ~> MAIL FROM:<info@hackerspace.by>
<~  250 2.1.0 <info@hackerspace.by> ok
 ~> RCPT TO:<jekhor@gmail.com>
<~  250 2.1.5 <jekhor@gmail.com> recipient ok
 ~> DATA
<~  354 Enter mail, end with "." on a line by itself
 ~> Date: Sun, 26 Aug 2018 23:44:47 +0300
 ~> To: jekhor@gmail.com
 ~> From: info@hackerspace.by
 ~> Subject: test Sun, 26 Aug 2018 23:44:47 +0300
 ~> Message-Id: <20180826234447.009028@localhost.localdomain>
 ~> X-Mailer: swaks v20170101.0 jetmore.org/john/code/swaks/
 ~>
 ~> This is a test mailing
 ~>
 ~> .
<~  250 2.0.0 Ok: queued on smtp1p.mail.yandex.net as 1535316290-P7v4CLO7ie-inniaxq7
 ~> QUIT
<~  221 2.0.0 Closing connection.
=== Connection closed with remote host.