Develop Reference

Sending mail with through python with roundcube

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()

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.

Google SMTP less secure applications

I am trying to send email via Google SMTP server using the following simple python and mailclient.
I am a bit confused about the part where Google flags this script as insecure and requires me to allow less secure applications to access the sender's gmail account.
Is there any way to solve this problem without having to allow less secure applications to access my gmail account.
#Make necessary imports
import mailclient
#Craft the message
msg = mailclient.Message("This will be the subject", "This will be the body content", 'sender#gmail.com', 'recipient#domain.com')
#Create server object with gmail
s = mailclient.Server('smtp.gmail.com', '587', 'sender#gmail.com', 'senderpassword', True)
#Send email
s.send(msg)

Hard to say, because Google is not very explicit for what they call unsecure applications, but I guess that they are applications that use ports 25 or 587. On those ports, the connection is initially established on an unencrypted channel, and becomes encrypted only when (and if) the STARTTLS command is issued.
So I guess that you should try to establish a connection directly over SSL on port 465. I do not know whether it is possible using mailclient but with the standard library modules, it should be as simple as:
import smtplib
from email.message import EmailMessage
msg = EmailMessage()
msg['Subject'] = "This will be the subject"
msg['From'] = 'sender#gmail.com'
msg['To'] = [ 'recipient#domain.com' ]
msg.set_content("This will be the body content")
server = smtplib.SMTP_SSL('smtp.gmail.com')
server.login('sender#gmail.com', 'senderpassword')
server.send_message(msg)
server.quit()

AOL mail rejected using smtplib

I'm using smtplib to send email via AOL account, but after successful authentication it gets rejected with following error.
reply: '521 5.2.1 : AOL will not accept delivery of this message.\r\n'
reply: retcode (521); Msg: 5.2.1 : AOL will not accept delivery of this message.
data: (521, '5.2.1 : AOL will not accept delivery of this message.')
Here's explanation for this error.
The SMTP reply code 521 indicates an Internet mail host DOES NOT ACCEPT
incoming mail. If you are receiving this error it indicates a configuration
error on the part of the recipient organisation, i.e. inbound e-mail traffic
is being routed through a mail server which has been explicitly configured
(intentionally or not) to NOT ACCEPT incoming e-mail.
Recipient mail (in my script) is valid (gmail) address and after this debug message mail gets rejected.
send: 'Content-Type: text/plain; charset="us-ascii"\r\nMIME-Version: 1.0\r\nContent-Transfer-Encoding: 7bit\r\nSubject: My reports\r\nFrom: myAOLmail#aol.com\r\nTo: reportmail#gmail.com\r\n\r\nDo you have my reports?\r\n.\r\n'
Here's short version of code:
r_mail = MIMEText('Do you have my reports?')
r_mail['Subject'] = 'My reports'
r_mail['From'] = e_mail
r_mail['To'] = 'reportmail#gmail.com'
mail = smtplib.SMTP("smtp.aol.com", 587)
mail.set_debuglevel(True)
mail.ehlo()
mail.starttls()
mail.login(e_mail, password)
mail.sendmail(e_mail, ['reportmail#gmail.com'] , r_mail.as_string())
Is this some kind of permission problem because I'm successfully sending same email with Yahoo account without any problems?

I guess that AOL doesn't allow relay access by default or you have not configured it manually. The error you get says that aol doesn't have recipient you want to send message. In this case if you want to send email to gmail account try to connect to gmail SMPT server instead of AOL.
Change smpt server to gmail-smtp-in.l.google.com for example and turn off authentication.

Was running into 5.2.1 : AOL will not accept delivery of this message. from the AOL SMTP relay myself. What I ended up needing was valid From and To headers in the MIME message body, as opposed to just the SMTP connection.
In your particular case there could be any number of reasons for getting this 5.2.1 bounce. The postmaster.aol.com site has some helpful tools to diagnose, as well as some pretty vague documentation for this specific error message. In my case I ended up packet sniffing the SMTP messages that my Thunderbird email client was sending vs. the Python script, and eventually spotted the difference.
postmaster.aol.com documentation:
https://postmaster.aol.com/error-codes
AOL will not accept delivery of this message
This is a permanent bounce due to:
RFC2822 From domain does not match the rDNS of sending server.
RFC 2822 FROM address does not have an A record and is not a valid domain.
IP has a poor reputation and mail is sent to multiple recipients.
There are multiple From address in the mail headers and the IP reputation is poor.
My Python function for sending mail through smtp.aol.com:
import smtplib
from email.mime.multipart import MIMEMultipart
from email.mime.text import MIMEText
def genEmail(user, passwd, to, subject, message):
smtp=smtplib.SMTP_SSL('smtp.aol.com',465)
smtp.login(user, passwd)
msg = MIMEMultipart()
msg['Subject'] = subject
msg['From'] = user # This has to exist, and can't be forged
msg['To'] = to
msg.attach(MIMEText(message, 'plain'))
smtp.sendmail(user, to, msg.as_string())
smtp.quit()

Python 2: SMTPServerDisconnected: Connection unexpectedly closed

I have a small problem with sending an email in Python:
#me == my email address
#you == recipient's email address
me = "some.email#gmail.com"
you = "some_email2#gmail.com"
# Create message container - the correct MIME type is multipart/alternative.
msg = MIMEMultipart('alternative')
msg['Subject'] = "Alert"
msg['From'] = me
msg['To'] = you
# Create the body of the message (a plain-text and an HTML version).
html = '<html><body><p>Hi, I have the following alerts for you!</p></body></html>'
# Record the MIME types of both parts - text/plain and text/html.
part2 = MIMEText(html, 'html')
# Attach parts into message container.
# According to RFC 2046, the last part of a multipart message, in this case
# the HTML message, is best and preferred.
msg.attach(part2)
# Send the message via local SMTP server.
s = smtplib.SMTP('aspmx.l.google.com')
# sendmail function takes 3 arguments: sender's address, recipient's address
# and message to send - here it is sent as one string.
s.sendmail(me, you, msg.as_string())
s.quit()
So before now, my program didn't give me an error, but it also didn't send me an email. And now python gives me an error:
SMTPServerDisconnected: Connection unexpectedly closed
How can I fix this?

TLDR: switch to authenticated connection over TLS.
Most probably the gmail server rejected the connection after the data command (very nasty of them to do so at this stage :). The actual message is most probably this one:
retcode (421); Msg: 4.7.0 [ip.octets.listed.here 15] Our system has detected an unusual rate of
4.7.0 unsolicited mail originating from your IP address. To protect our
4.7.0 users from spam, mail sent from your IP address has been temporarily
4.7.0 rate limited. Please visit
4.7.0 https://support.google.com/mail/answer/81126 to review our Bulk Email
4.7.0 Senders Guidelines. qa9si9093954wjc.138 - gsmtp
How do I know that? Because I've tried it :) with the s.set_debuglevel(1), which prints the SMTP conversation and you can see firsthand what's the issue.
You've got two options here:
Continue using that relay; as explained by Google, it's unencrypted gmail-to-gmail only, and you have to un-blacklist your ip through their procedure
The most fool-proof option is to switch to TLS with authentication
Here's how the changed source looks like:
# skipped your comments for readability
import smtplib
from email.mime.multipart import MIMEMultipart
from email.mime.text import MIMEText
me = "some.email#gmail.com"
my_password = r"your_actual_password"
you = "some.email2#gmail.com"
msg = MIMEMultipart('alternative')
msg['Subject'] = "Alert"
msg['From'] = me
msg['To'] = you
html = '<html><body><p>Hi, I have the following alerts for you!</p></body></html>'
part2 = MIMEText(html, 'html')
msg.attach(part2)
# Send the message via gmail's regular server, over SSL - passwords are being sent, afterall
s = smtplib.SMTP_SSL('smtp.gmail.com')
# uncomment if interested in the actual smtp conversation
# s.set_debuglevel(1)
# do the smtp auth; sends ehlo if it hasn't been sent already
s.login(me, my_password)
s.sendmail(me, you, msg.as_string())
s.quit()
Now, if try to 'cheat' the system and send with a different (non-gmail) address it's gonna a) require you to connect to a different hostname (some of the MX records for gmail), then b) stop you and close the connection on the grounds of blacklisted ip, and c) do reverse DNS, DKIM and lots of other countermeasures to make sure you're actually in control of the domain you presented in the MAIL FROM: address.
Finally, there's also option 3) - use any other email relaying service, there are tons of good ones :)

I Had the same issue and solved it just by specifying the right port like this:
smtplib.SMTP('smtp.gmail.com', 587)

Using smtplib.SMTP_SSL() instead of smtplib.SMTP() works for me. Try this.

I have realised a strange behavior. I have used similar codes mentioned both the question and answers. My code has been working for the last days. However, today I encountered the error message mentioned in the question.
My solution:
I had tried my successful attempt via library network. Today I have tried it via Starbucks network (over captive portal). I changed it to my mobile network. It started working again.
Possibly, Google rejects requests from unreliable networks.

I was facing the same problem. In my case, password was changed just few days back. So, it was giving the error. As I updated the password in code, its working like a charm...!!!

Googlers: I had a test smtp server running locally. I was getting this error because I was shutting down the local smtp server before closing the client smtp.

with smtplib.SMTP_SSL("smtp.mail.yahoo.com", port=465) as connection:
connection.login(
user=my_email,
password=my_password
)
connection.sendmail(
from_addr=my_email,
to_addrs=friend_address,
msg=f"Subject:Text\n\n"
f"Body of the text"
)
This is my code. I hope it will be helpful.

python smtp gmail authentication error (sending email through gmail smtp server)

I have the following code
import smtplib
from email.mime.text import MIMEText
smtpserver = 'smtp.gmail.com'
AUTHREQUIRED = 1 # if you need to use SMTP AUTH set to 1
smtpuser = 'admin#myhost.com' # for SMTP AUTH, set SMTP username here
smtppass = '123456' # for SMTP AUTH, set SMTP password here
RECIPIENTS = ['online8#gmail.com']
SENDER = 'admin#myhost.com'
msg = MIMEText('dsdsdsdsds\n')
msg['Subject'] = 'The contents of iii'
msg['From'] = 'admin#myhost.com'
msg['To'] = ''online8#gmail.com''
mailServer = smtplib.SMTP('smtp.gmail.com',587)
mailServer.ehlo()
mailServer.starttls()
mailServer.ehlo()
mailServer.login(smtpuser, smtppass)
mailServer.sendmail(smtpuser,RECIPIENTS,msg.as_string())
mailServer.close()
this code works fine on my desktop. but it failed with this error
smtplib.SMTPAuthenticationError: (535, '5.7.1 Username and Password not accepted. Learn more at\n5.7.1 http://mail.google.com/support/bin/answer.py?answer=14257 21sm4713429agd.11')
on my linux server.
Not sure what went wrong, should i open some port on my linux server?

Port 587 obviously needs to be open, but it probably is (or you wouldn't have gotten the detailed error msg in question). Python 2.5 vs 2.6 should make no difference. I think the issue has to do with "solving a captcha" once on the computer for which logins are currently getting rejected; follow the detailed instructions at the URL in the error message, i.e., http://mail.google.com/support/bin/answer.py?answer=14257

import random,time
for i in range(1,100):
y=random.randint(30,300)
time.sleep(y)
print ("Mailing for fun, Mail No: " + str(i))
msg = MIMEText('Testing mailing \n Mail No:' + str(i))
msg['Subject'] = 'Mail Number: ' + str(i)
Randomizing the mail interval to check smtp behavior :)
With a bit addition n modification, I got this to work to check our intermittent mail bouncing.