#
# Wesleyan University
# COMP 360, Section 1, Fall 2016
# V. Manfredi
#
# Sending email using openssl
#

#=========================================================
# Connect to mail server. E.g.,
#=========================================================

# Wesleyan mail server:

    openssl s_client -crlf -connect exchange2010.wesleyan.edu:465

# Gmail mail server

    openssl s_client -crlf -connect smtp.gmail.com:465

# From the server you should see something like

    220 exchcas3.wesad.wesleyan.edu Microsoft ESMTP MAIL Service ready at Wed, 21 Sep 2016 12:19:27 -0400

	OR

    220 smtp.gmail.com ESMTP 44sm19281105qtt.5 - gsmtp

#=========================================================
# Say hello
#=========================================================

# Type at hanging prompt a HELO or Extended HELO (EHLO)
# including your sending domain (although not clear it matters
# what you type here), and I've just been typing my email username

    EHLO vumanfredi

# From the server you should see something like the following in response

    250-exchcas3.wesad.wesleyan.edu Hello [129.133.7.96]

	OR

    250-smtp.gmail.com at your service, [129.133.188.219]

#=========================================================
# Authentication time
#=========================================================

# First convert your username and password to binary. Type
# these commands in a separate terminal, using your username
# and replacing password with your password. You'll get
# back some base64 encoded strings that you will enter at the
# hanging SMTP prompt. If you're using gmail (and 2-factor
# authentication you may need to generate an app password,
# see the following website for more details

    https://support.google.com/accounts/answer/185833?p=InvalidSecondFactor&visit_id=1-636100677231869734-2558592835&rd=1

    perl -MMIME::Base64 -e 'print encode_base64("username\@wesleyan.edu")'
    perl -MMIME::Base64 -e 'print encode_base64("password")'

# Enter those base64 encoded strings at the SMTP prompt
# To do so, first type

    auth login

# You should see in response, something like

334 VXNlcm5hbWU6

# Paste your username string and press enter. You should see in response
# something like,

334 UGFzc3dvcmQ6

# Now paste your password string. You should see in response:

250 2.1.5 Recipient OK

#=========================================================
# Generate the email
#=========================================================

# Specify the sender by typing the following at prompt.
# Note the use of brackets: < >

    MAIL FROM: <username@wesleyan.edu>

# You should see in response

    250 2.1.0 Sender OK

# Specify the receiver by typing the following at prompt.
# Note that "rcpt to:" is in lower case. The "r" is really
# all that needs to be lower case. Upper case R tells openssl
# you want to renegotiate, which you do not want to do. So
# this is just a hack for dealing with openssl

    rcpt to: <username@gmail.com>

# You should see in response

    250 2.1.5 Recipient OK

# Now generate and send the data. Type at the prompt

    DATA

# You should see in response

    354 Start mail input; end with <CRLF>.<CRLF>

	OR

    354  Go ahead qkg.23 - gsmtp

# Enter the data to send. E.g.,

    From: me
    To: you
    Subject: test
    .

# You should see in response, something like

     250 2.6.0 <exchcas3.wesad.wesleyan.edu> [InternalId=37375198] Queued mail for delivery

	OR

    250 2.0.0 OK qkg.23 - gsmtp

#=========================================================
# Done. Close connection
#=========================================================

    QUIT