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Python Sending email using SMTP - target machine actively refused connection

I am trying to send email internally within work using the smtplib package in Python. I am running this script behind a VPN using the same proxy settings for R and Spyder.
I use the following code which was adapted from mkyoung.com
import smtplib
to = 'foo#foo-corporate.com'
corp_user = 'foo#foo-corporate.com'
corp_pwd = 'password'
smtpserver = smtplib.SMTP_SSL(local_hostname="smtp://foo-corporate.com", port = 25)
smtpserver.connect()
Once i try the last line smtpserver.connect(), I get the error message:
[WinError 10061] No connection could be made because the target machine actively refused it
This would suggest that the server is not accepting SMTP requests.
However if i execute the same script in R using the Blastula package It works fine.
Can anyone suggest how I can trouble shoot this?
library(blastula)
create_smtp_creds_key(
id = "email_creds",
user = "foo#foo-corporate.com",
host = "smtp://foo-corporate.com",
port = 25,
use_ssl = TRUE
)
email <-
compose_email(
body = md(" Hello,
This is a test email
"))
# Sending email by SMTP using a credentials file
email %>%
smtp_send(
to = "foo#foo-corporate.com",
from = "foo#foo-corporate.com",
subject = "Testing the `smtp_send()` function",
credentials = creds_key("email_creds")
)

Seems like the context is not needed at all.
This is an example using TLS. Give it a try, at least in my environment, this worked.
import smtplib
smtp_server = 'mail.example.com'
port = 587 # For starttls
sender_email = "from#mail.com"
receiver_email = 'to#mail.com'
password = r'password'
message = f'''\
From: from-name <from#mail.com>
To: to-name <to#mail.com>
Subject: testmail
testmail
'''
try:
server = smtplib.SMTP(smtp_server, port)
server.ehlo()
server.starttls()
server.ehlo()
server.login(sender_email, password)
server.sendmail(sender_email, receiver_email, message)
except Exception as e:
# Print any error messages to stdout
print(e)
finally:
server.quit()

Hi #user99999 and #Ovski
Thank you for investigating this for me.
I managed to finally get it working with the below code
import smtplib
import ssl
to = 'foo#foo-corporate.com'
corp_user = 'foo#foo-corporate.com'
corp_pwd = 'password'
smtpserver = smtplib.SMTP_SSL("smtp://foo-corporate.com")
smtp_server.ehlo()
smtp_server.login(corp_user, corp_pwd)
msg_to_send = '''
hello world!
'''
smtp_server.sendmail(user,to,msg_to_send)
smtp_server.quit()

Error in sending email from a Amazon Lambda function using python SMTP library

I am trying to send an email from an Amazon Lambda function using python's SMTP library. Here is my code so far:
import smtplib
from_addr = 'fromemailid#company.com'
username = 'user1'
password = 'pwd'
def send_email():
to_addrs = "user1#company.com"
msg = "\r\n".join([
"From: fromemailid#company.com",
"To: "+to_addrs,
"Subject: Test Email ",
"",
"Hello" + ", \n This is a test email"
])
server = smtplib.SMTP('123.45.678.9')
server.ehlo()
server.starttls()
server.login(username, password)
server.sendmail(from_addr, to_addrs, msg)
server.quit()
if __name__ == '__main__':
send_email()
In my code above the hostname is of the format of an ip_address. When I execute this code I get error as TimeoutError: 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 tried server = smtplib.SMTP('123.45.678.9', local_hostname = 'mail.company.com') as well but same error. If I try server = smtplib.SMTP('mail.company.com') then I get following error - [Errno -2] Name or service not known. How can send an email from within the lambda function?

TimeoutError trying to send an email with smtplib

I am trying to use Python's smtplib module to send an email but I keep receiving a TimeoutError.
import smtplib
def send():
try:
server = smtplib.SMTP('smtp.gmail.com', 587)
server.ehlo()
server.starttls()
server.login(email, password) # Email and password are already defined
print('Enter recipient: ')
recipient = input()
print('Enter subject:')
subject = input() + '\n'
print('Enter body:')
body = input()
server.sendmail(email, recipient, body)
server.quit()
except TimeoutError as e:
print (str(e))
This code recieves a:
[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

It looks like you have not enabled "Allow Less Secure Apps" option in your GMail account.
Here's more officially from Google,
https://support.google.com/accounts/answer/6010255?hl=en

If you are using a VPN connection, disable it first. It worked for me.

Use port 587. I was getting the same error but when I entered 587 as port it worked
smtplib.SMTP("smtp.gmail.com", 587)

Open relay python

#!/usr/bin/python
import smtplib
message = """From: Test <test#fromdomain.com>
To: test<test#todomain.com>
Subject: SMTP test
This is test
"""
try:
smtpObj = smtplib.LMTP('exhange.intranet',25)
smtpObj.sendmail(sender, receivers, message)
print "Successfully sent email"
except SMTPException:
print "Error: unable to send email"
Hello basiclly im testing open relay server and here is question is there other method to send mail without any authetication than LMTP ?How i can implement this with SMTP which paramter is that ?
Sending a mail with only smtp is getting blocked on exhange easyli, there must be included NOT authetication information for exhange to pass it through.

To use SMTP without authentication, use code like the following:
smtpObj = smtplib.SMTP('exhange.intranet',25)
smtpObj.sendmail(sender, receivers, message)
smtpObj.quit()

No email sending using smtplib - python

import smtplib
sender = 'den.callanan#gmail.com'
receiver = ['callanden#gmail.com']
message = """From: From Person <den.callanan#gmail.com>
To: To Person <callanden#gmail.com>
Subject: SMTP e-mail test
This is a test e-mail message.
"""
try:
print("trying host and port...")
smtpObj = smtplib.SMTP('smtp.gmail.com', 465)
print("sending mail...")
smtpObj.sendmail(sender, receiver, message)
print("Succesfully sent email")
except SMTPException:
print("Error: unable to send email")
I've created two new email accounts (above), both on the same server (gmail) to test this.
It reaches the point in which it prints "trying host and port..." and does not go any further. So the problem should be with the address and port number I entered. But according to gmail's outgoing mail server details i've inputted them correctly. Any ideas what's wrong?
If I remove the port number or try a different port number such as 587 i'm provided with an error.

Sending email via Gmail's SMTP servers requires TLS and authentication. To authenticate, you will need to make an application-specific password for your account.
This script worked for me (though I used my own GMail email address and my own application-specific password). In the code below, replace APPLICATION_SPECIFIC_PASSWORD with the password you generated.
import smtplib
sender = 'den.callanan#gmail.com'
receiver = ['callanden#gmail.com']
message = """From: From Person <den.callanan#gmail.com>
To: To Person <callanden#gmail.com>
Subject: SMTP e-mail test
This is a test e-mail message.
"""
try:
print("trying host and port...")
smtpObj = smtplib.SMTP_SSL('smtp.gmail.com', 465)
smtpObj.login("den.callanan#gmail.com", "APPLICATION_SPECIFIC_PASSWORD")
print("sending mail...")
smtpObj.sendmail(sender, receiver, message)
print("Succesfully sent email")
except smtplib.SMTPException:
print("Error: unable to send email")
import traceback
traceback.print_exc()
(To debug the problem, I added the print-traceback code in the except statement. The exceptions had specific information on how to get it to work. The code hung when accessing port 465, I think because of problems with TLS negotiation, so I had to try using port 587; then I got good debugging info that explained what to do.)
You can see info on the SMTP_SSL object here.