#!/usr/bin/env python3

# Code credit to PyMoTW3

# This is not an exact copy, and was only used as a

# study aid in the process of understanding `smtplib`

# and its use.

import sys

import smtplib

import email.utils

import getpass

from email.mime.text import MIMEText

recipient = input("Recipient address: ")

server_name = input("Mail Server Name: ")

try:

server_port = int(input("Mail Server Port: "))

except ValueError:

sys.exit("Expecting an integer as Port number!")

use_tls = input("Use TLS? [Y/N]").lower()

username = input("Username: ")

# Get the password without echoing

password = getpass.getpass(f"Password for {username}: ")

message = MIMEText("Hello, how are you?")

message.set_unixfrom("Author")

message["To"] = email.utils.format(("Recipient", "recipient"))

message["From"] = email.utils.format(("Author", "arvimal@yahoo.in"))

message["Subject"] = "Test mail"

if use_tls == "y":

print("Setting up a secure connection.")

else:

print("TLS not activated, connection insecure!")

mail_server = smtplib.SMTP(server_name, server_port)

# Activate the debuglevel

mail_server.set_debuglevel(True)

# The EHLO flag send from the client, will prompt the

# server to send back the features it support, to the

# client.

mail_server.ehlo()

# The `has_extn()` method can be used to list the features

# the server supports. Here, if the server supports TLS, we

# try to use it.

if mail_server.has_extn("STARTTLS"):

print("Connecting using TLS.")

mail_server.starttls()

# We need to use the `EHLO` method once again,

# to identify ourself for the TLS session

mail_server.ehlo()

else:

print(f"{server_name} does not support TLS")

if mail_server.has_extn("AUTH"):

print("Trying to authenticate using username/password")

mail_server.login(username, password)

else:

print(f"{server_name} does not support authentication")

mail_server.sendmail("arvimal@yahoo.in", [recipient], message.as_string())

# Quit once the message has been send

mail_server.quit()