How to send email using simple SMTP commands via Gmail?

Question

For educational purposes, I need to send an email through an SMTP server, using SMTP\'s fundamental and simple rules.

I was able to do that using smtp4dev. I

Answer 1

As no one has mentioned - I would suggest to use great tool for such purpose - swaks

# yum info swaks
Installed Packages
Name        : swaks
Arch        : noarch
Version     : 20130209.0
Release     : 3.el6
Size        : 287 k
Repo        : installed
From repo   : epel
Summary     : Command-line SMTP transaction tester
URL         : http://www.jetmore.org/john/code/swaks
License     : GPLv2+
Description : Swiss Army Knife SMTP: A command line SMTP tester. Swaks can test
            : various aspects of your SMTP server, including TLS and AUTH.

It has a lot of options and can do almost everything you want.

GMAIL: STARTTLS, SSLv3 (and yes, in 2016 gmail still support sslv3)

$ echo "Hello world" | swaks -4 --server smtp.gmail.com:587 --from user@gmail.com --to user@example.net -tls --tls-protocol sslv3 --auth PLAIN --auth-user user@gmail.com --auth-password 7654321 --h-Subject "Test message" --body -
=== Trying smtp.gmail.com:587...
=== Connected to smtp.gmail.com.
<-  220 smtp.gmail.com ESMTP h8sm76342lbd.48 - gsmtp
 -> EHLO www.example.net
<-  250-smtp.gmail.com at your service, [193.243.156.26]
<-  250-SIZE 35882577
<-  250-8BITMIME
<-  250-STARTTLS
<-  250-ENHANCEDSTATUSCODES
<-  250-PIPELINING
<-  250-CHUNKING
<-  250 SMTPUTF8
 -> STARTTLS
<-  220 2.0.0 Ready to start TLS
=== TLS started with cipher SSLv3:RC4-SHA:128
=== TLS no local certificate set
=== TLS peer DN="/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com"
 ~> EHLO www.example.net
<~  250-smtp.gmail.com at your service, [193.243.156.26]
<~  250-SIZE 35882577
<~  250-8BITMIME
<~  250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
<~  250-ENHANCEDSTATUSCODES
<~  250-PIPELINING
<~  250-CHUNKING
<~  250 SMTPUTF8
 ~> AUTH PLAIN AGFhQxsZXguaGhMGdATGV4X2hoYtYWlsLmNvbQBS9TU1MjQ=
<~  235 2.7.0 Accepted
 ~> MAIL FROM:
<~  250 2.1.0 OK h8sm76342lbd.48 - gsmtp
 ~> RCPT TO:
<~  250 2.1.5 OK h8sm76342lbd.48 - gsmtp
 ~> DATA
<~  354  Go ahead h8sm76342lbd.48 - gsmtp
 ~> Date: Wed, 17 Feb 2016 09:49:03 +0000
 ~> To: user@example.net
 ~> From: user@gmail.com
 ~> Subject: Test message
 ~> X-Mailer: swaks v20130209.0 jetmore.org/john/code/swaks/
 ~>
 ~> Hello world
 ~>
 ~>
 ~> .
<~  250 2.0.0 OK 1455702544 h8sm76342lbd.48 - gsmtp
 ~> QUIT
<~  221 2.0.0 closing connection h8sm76342lbd.48 - gsmtp
=== Connection closed with remote host.

YAHOO: TLS aka SMTPS, tlsv1.2

$ echo "Hello world" | swaks -4 --server smtp.mail.yahoo.com:465 --from user@yahoo.com --to user@gmail.com --tlsc --tls-protocol tlsv1_2 --auth PLAIN --auth-user user@yahoo.com --auth-password 7654321 --h-Subject "Test message" --body -
=== Trying smtp.mail.yahoo.com:465...
=== Connected to smtp.mail.yahoo.com.
=== TLS started with cipher TLSv1.2:ECDHE-RSA-AES128-GCM-SHA256:128
=== TLS no local certificate set
=== TLS peer DN="/C=US/ST=California/L=Sunnyvale/O=Yahoo Inc./OU=Information Technology/CN=smtp.mail.yahoo.com"
<~  220 smtp.mail.yahoo.com ESMTP ready
 ~> EHLO www.example.net
<~  250-smtp.mail.yahoo.com
<~  250-PIPELINING
<~  250-SIZE 41697280
<~  250-8 BITMIME
<~  250 AUTH PLAIN LOGIN XOAUTH2 XYMCOOKIE
 ~> AUTH PLAIN AGFhQxsZXguaGhMGdATGV4X2hoYtYWlsLmNvbQBS9TU1MjQ=
<~  235 2.0.0 OK
 ~> MAIL FROM:
<~  250 OK , completed
 ~> RCPT TO:
<~  250 OK , completed
 ~> DATA
<~  354 Start Mail. End with CRLF.CRLF
 ~> Date: Wed, 17 Feb 2016 10:08:28 +0000
 ~> To: user@gmail.com
 ~> From: user@yahoo.com
 ~> Subject: Test message
 ~> X-Mailer: swaks v20130209.0 jetmore.org/john/code/swaks/
 ~>
 ~> Hello world
 ~>
 ~>
 ~> .
<~  250 OK , completed
 ~> QUIT
<~  221 Service Closing transmission
=== Connection closed with remote host.

I have been using swaks to send email notifications from nagios via gmail for last 5 years without any problem.