Send smtp message

[barry]

I am stumped with trying to use the Python smtplib module. I have followed the instructions via https://pymotw.com/2/smtplib/. I am using the example from the second part "Authentication and Encryption":

import smtplib
import email.utils
from email.mime.text import MIMEText
import getpass

# Prompt the user for connection info
to_email = raw_input('Recipient: ')
servername = raw_input('Mail server name: ')
username = raw_input('Mail user name: ')
password = getpass.getpass("%s's password: " % username)

# Create the message
msg = MIMEText('Test message from PyMOTW.')
msg.set_unixfrom('author')
msg['To'] = email.utils.formataddr(('Recipient', to_email))
msg['From'] = email.utils.formataddr(('Author', '[email protected]'))
msg['Subject'] = 'Test from PyMOTW'

server = smtplib.SMTP(servername)
try:
    server.set_debuglevel(True)

    # identify ourselves, prompting server for supported features
    server.ehlo()

    # If we can encrypt this session, do it
    if server.has_extn('STARTTLS'):
        server.starttls()
        server.ehlo() # re-identify ourselves over TLS connection

    server.login(username, password)
    server.sendmail('[email protected]', [to_email], msg.as_string())
finally:
    server.quit()

But, I only get so far:

Recipient: [email protected]
Mail server name: smtpauth.isp.net
Mail user name: [email protected]
[email protected]'s password:
send: 'ehlo 70WLKG105279.houtx.lcl\r\n'
reply: '250-smtp.gmail.com at your service, [50.58.210.12]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-STARTTLS\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-CHUNKING\r\n'
reply: '250 SMTPUTF8\r\n'
reply: retcode (250); Msg: smtp.gmail.com at your service, [50.58.210.12]
SIZE 35882577
8BITMIME
STARTTLS
ENHANCEDSTATUSCODES
PIPELINING
CHUNKING
SMTPUTF8
send: 'STARTTLS\r\n'
reply: '220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: 2.0.0 Ready to start TLS

Any suggestions would be much appreciated.

Barry
Python 2.7.13 on Win32

[barry]

Have also tried a slightly modified version (https://pymotw.com/3/smtplib/), using Python 3.5.3:

import smtplib
import email.utils
from email.mime.text import MIMEText
import getpass

# Prompt the user for connection info
to_email = input('Recipient: ')
servername = input('Mail server name: ')
serverport = input('Server port: ')
if serverport:
    serverport = int(serverport)
else:
    serverport = 25
use_tls = input('Use TLS? (yes/no): ').lower()
username = input('Mail username: ')
password = getpass.getpass("%s's password: " % username)

# Create the message
msg = MIMEText('Test message from PyMOTW.')
msg.set_unixfrom('author')
msg['To'] = email.utils.formataddr(('Recipient', to_email))
msg['From'] = email.utils.formataddr(('Author',
                                      '[email protected]'))
msg['Subject'] = 'Test from PyMOTW'

if use_tls == 'yes':
    print('starting with a secure connection')
    server = smtplib.SMTP_SSL(servername, serverport)
else:
    print('starting with an insecure connection')
    server = smtplib.SMTP(servername, serverport)
try:
    server.set_debuglevel(True)

    # identify ourselves, prompting server for supported features
    server.ehlo()

    # If we can encrypt this session, do it
    if server.has_extn('STARTTLS'):
        print('(starting TLS)')
        server.starttls()
        server.ehlo()  # reidentify ourselves over TLS connection
    else:
        print('(no STARTTLS)')

    if server.has_extn('AUTH'):
        print('(logging in)')
        server.login(username, password)
    else:
        print('(no AUTH)')

    server.sendmail('[email protected]',
                    [to_email],
                    msg.as_string())
finally:
    server.quit()

Resulting in:

Python 3.5.3 |Continuum Analytics, Inc.| (default, Feb 22 2017, 21:28:42) [MSC v.1900 64 bit (AMD64)] on win32
Type "copyright", "credits" or "license()" for more information.
>>> 
============== RESTART: C:/temp/Barry/Scripts/PyMOTW_example.py ==============
Recipient: [email protected]
Mail server name: smtp.mailserver.com
Server port: 895
Use TLS? (yes/no): yes
Mail username: myusername

Warning (from warnings module):
  File "C:\Program Files\ArcGIS\Pro\bin\Python\envs\arcgispro-py3\lib\getpass.py", line 101
    return fallback_getpass(prompt, stream)
GetPassWarning: Can not control echo on the terminal.
Warning: Password input may be echoed.
e166615's password: mypassword
starting with a secure connection
Traceback (most recent call last):
  File "C:/temp/Barry/Scripts/PyMOTW_example.py", line 28, in <module>
    server = smtplib.SMTP_SSL(servername, serverport)
  File "C:\Program Files\ArcGIS\Pro\bin\Python\envs\arcgispro-py3\lib\smtplib.py", line 1021, in __init__
    source_address)
  File "C:\Program Files\ArcGIS\Pro\bin\Python\envs\arcgispro-py3\lib\smtplib.py", line 251, in __init__
    (code, msg) = self.connect(host, port)
  File "C:\Program Files\ArcGIS\Pro\bin\Python\envs\arcgispro-py3\lib\smtplib.py", line 335, in connect
    self.sock = self._get_socket(host, port, self.timeout)
  File "C:\Program Files\ArcGIS\Pro\bin\Python\envs\arcgispro-py3\lib\smtplib.py", line 1027, in _get_socket
    self.source_address)
  File "C:\Program Files\ArcGIS\Pro\bin\Python\envs\arcgispro-py3\lib\socket.py", line 712, in create_connection
    raise err
  File "C:\Program Files\ArcGIS\Pro\bin\Python\envs\arcgispro-py3\lib\socket.py", line 703, in create_connection
    sock.connect(sa)
TimeoutError: [WinError 10060] A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond

[shapeg]

Hi Barry, did you get it working? I have code that works fine with the Gmail server, but I can't get it to work with other email servers such as mail.com or outlook.co.nz. regards Shane