# -*- mode: python; indent-tabs-mode: nil; py-indent-offset: 4; coding: utf-8 -*-
# https://stackoverflow.com/questions/5239797/python-smtplib-proxy-support
# https://stackoverflow.com/questions/19642726/testing-python-smtp-email-service
import socket
import smtplib

import socks

class ProxySMTP(smtplib.SMTP):
    def __init__(self, host='', port=0, local_hostname=None,
                 timeout=socket._GLOBAL_DEFAULT_TIMEOUT,
                 source_address=None, proxy_addr=None, proxy_port=None):
        """Initialize a new instance.

        If specified, `host' is the name of the remote host to which to
        connect.  If specified, `port' specifies the port to which to connect.
        By default, smtplib.SMTP_PORT is used.  If a host is specified the
        connect method is called, and if it returns anything other than a
        success code an SMTPConnectError is raised.  If specified,
        `local_hostname` is used as the FQDN of the local host in the HELO/EHLO
        command.  Otherwise, the local hostname is found using
        socket.getfqdn(). The `source_address` parameter takes a 2-tuple (host,
        port) for the socket to bind to as its source address before
        connecting. If the host is '' and port is 0, the OS default behavior
        will be used.

        """
        self._host = host
        self.timeout = timeout
        self.esmtp_features = {}
        self.command_encoding = 'ascii'
        self.source_address = source_address
        self.proxy_addr = proxy_addr
        self.proxy_port = proxy_port

        if host:
            (code, msg) = self.connect(host, port)
            if code != 220:
                self.close()
                raise smtplib.SMTPConnectError(code, msg)
        if local_hostname is not None:
            self.local_hostname = local_hostname
        else:
            # RFC 2821 says we should use the fqdn in the EHLO/HELO verb, and
            # if that can't be calculated, that we should use a domain literal
            # instead (essentially an encoded IP address like [A.B.C.D]).
            fqdn = socket.getfqdn()
            if '.' in fqdn:
                self.local_hostname = fqdn
            else:
                # We can't find an fqdn hostname, so use a domain literal
                addr = '127.0.0.1'
                try:
                    addr = socket.gethostbyname(socket.gethostname())
                except socket.gaierror:
                    pass
                self.local_hostname = '[%s]' % addr

    def _get_socket(self, host, port, timeout):
        # This makes it simpler for SMTP_SSL to use the SMTP connect code
        # and just alter the socket connection bit.
        if self.debuglevel > 0:
            self._print_debug('connect: to', (host, port), self.source_address)
        return socks.create_connection((host, port),
                                       proxy_type=socks.PROXY_TYPE_SOCKS5,
                                       timeout=timeout,
                                       proxy_addr=self.proxy_addr,
                                       proxy_port=self.proxy_port)

# And to use:

if __name__ == '__main__':
    user_email, user_pass = 'foo', 'bar'
    email_server = ProxySMTP('smtp.gmail.com', 587,
                             proxy_addr='127.0.0.1',
                             proxy_port=9050,
                             timeout=20)
    email_server.starttls()
    try:
        email_server.login(user_email, user_pass)
    except smtplib.SMTPAuthenticationError as e:
        if len(e.args) > 1:
            code = e.args[0]
            if code = 535:
                # 5.7.8 Username and Password not accepted
                pass
        raise
    email_server.sendmail(user_email, recipient_list, msg.as_string())
    email_server.quit()