Sending mail with through python with roundcube

Question

Am trying to send mail with python using my rouncube webmail but when i run it outputs this error 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

I checked in my mail and my port is "290" which have provided but when i run the function the mail doesn't send. I know how to send with gmail by turning on less secure app access but don't know how to work around to send with my webmail.

I need your suggestion to work around it.

from smtplib import SMTP_SSL as SMTP
import logging, logging.handlers, sys
from email.mime.text import MIMEText



def send_message():
    text = '''
            Hello,

            Trying to send mail from my webmail in python 3. 

            Sincerely,

            My name
            '''

    message = MIMEText(text, 'plain')
    message['Subject'] = "Email Subject"
    my_email = 'joe@mycompany.com'

    # Email that you want to send a message
    message['To'] = my_email

    # You need to change here, depending on the email that you use.
    # For example, Gmail and Yahoo have different smtp. You need to know what it is.
    connection = SMTP('smtp.roundcube.com', 290)
    connection.set_debuglevel(True)

    # Attention: You can't put for example: 'your_address@email.com'.
    #            You need to put only the address. In this case, 'your_address'.
    connection.login('fred.kings', 'fredsw321a')

    try:
        # sendemail(<from address>, <to address>, <message>)
        connection.sendmail(my_email, my_email, message.as_string())
    finally:
        connection.close()



send_message()

Answer 1

I'm using:

• Ubuntu 18.04.4 LTS.
• Python 3.7.4
• Jupyter-Notebook 6.0.1
• Anaconda 1.7.2

I can successfully send an email through Python with Roundcube, executing the following script in a jupyter-notebook cell:

import smtplib

email = "myemail@mycompany.com"
password = "mypassword"
to = ["destination@dest.com"]

with smtplib.SMTP_SSL('mail.mycompany.com', 465) as smtp:

    smtp.login(email, password)

    subject = "testing mail sending"
    body = "the mail itself"

    msg = "Subject: {}\n\n{}".format(subject, body)

    smtp.sendmail(email, to, msg)

I found this information as follows (so you can find yours):

• Log into you company email.
• Look for the following image and click on it (Webmail Home).

• You'll see something like the following:

• Scroll down, looking for the following image and click on it (Configure Mail...).

• Look for the info at mail server section.

If there are using port 465 (such as in my case) it means that you want to use smtplib.SMTP_SSL instead of smtplib.SMTP.

NOTE: The previous worked for me from my personal computer, however, when I tried to use the same code, from my "virtual machine" at office, it does not work, which makes me think that there is a system limitation, and that the problem is not code-related.

Hope it helps, regards.