Error trying to send email to gmail python

Question

Hi all I am new to python. I am trying to send an image to my gmail account and getting the below error can someone help me with this. I have searched and searched and can't find an answer I have tried changing the port.

I have turned on the google less secure apps and not sure what else to do.

import smtplib
from email.mime.multipart import MIMEMultipart
from email.mime.base import MIMEBase
from email.mime.text import MIMEText
from email import encoders
import os

gmail_user = "you@gmail.com"
gmail_pwd = "pass"

to = "you@gmail.com"
subject = "Report"
text = "Picture report"
attach = 'web.png'

msg = MIMEMultipart()

msg['From'] = gmail_user
msg['To'] = to
msg['Subject'] = subject

msg.attach(MIMEText(text))

part = MIMEBase('application', 'octet-stream')
part.set_payload(open(attach, 'rb').read())
encoders.encode_base64(part)
part.add_header('Content-Disposition',
   'attachment; filename="%s"' % os.path.basename(attach))
msg.attach(part)

mailServer = smtplib.SMTP("smtp.gmail.com", 465)
mailServer.ehlo()
mailServer.starttls()
mailServer.ehlo()
mailServer.login(gmail_user, gmail_pwd)
mailServer.sendmail(gmail_user, to, msg.as_string())
# Should be mailServer.quit(), but that crashes...
mailServer.close()  

  Traceback (most recent call last):
  File "C:\Users\scott\Desktop\PYTHON NEW\newemail.py", line 31, in <module>
    mailServer = smtplib.SMTP("smtp.gmail.com", 465)
  File "C:\Users\scott\AppData\Local\Programs\Python\Python36-32\lib\smtplib.py", line 251, in __init__
    (code, msg) = self.connect(host, port)
  File "C:\Users\scott\AppData\Local\Programs\Python\Python36-32\lib\smtplib.py", line 337, in connect
    (code, msg) = self.getreply()
  File "C:\Users\scott\AppData\Local\Programs\Python\Python36-32\lib\smtplib.py", line 393, in getreply
    raise SMTPServerDisconnected("Connection unexpectedly closed")
smtplib.SMTPServerDisconnected: Connection unexpectedly closed

i have changed the port to 587 and got a different error

Traceback (most recent call last):
  File "C:\Users\scott\Desktop\PYTHON NEW\newemail.py", line 35, in <module>
    mailServer.login(gmail_user, gmail_pwd)
  File "C:\Users\scott\AppData\Local\Programs\Python\Python36-32\lib\smtplib.py", line 729, in login
    raise last_exception
  File "C:\Users\scott\AppData\Local\Programs\Python\Python36-32\lib\smtplib.py", line 720, in login
    initial_response_ok=initial_response_ok)
  File "C:\Users\scott\AppData\Local\Programs\Python\Python36-32\lib\smtplib.py", line 641, in auth
    raise SMTPAuthenticationError(code, resp)
smtplib.SMTPAuthenticationError: (534, b'5.7.14 <https://accounts.google.com/signin/continue?sarp=1&scc=1&plt=AKgnsbt4\n5.7.14 ah5smKPNBMdR8EDhHji_lOLermVkofD0XZiYZtx04cUZGJIvjm6scA9FeCEhJhB--aeW58\n5.7.14 O3uS9IVuNfqKe4HYqXgdBMbvtMSOSSMM4oGYwlvDIoXpIK0IJYKSyAfvPyPcjiF8Q_Es4n\n5.7.14 33gUceqr9ZjlNI066kXt-uTq2V39X6YUS2-ixCCKfoozS9zoQ1KJuLSWU1IhB3gTsGtB9m\n5.7.14 N-AEdgucbByvuI7zr2KG-DZwlvrWw> Please log in via your web browser and\n5.7.14 then try again.\n5.7.14  Learn more at\n5.7.14  https://support.google.com/mail/answer/78754 b65sm27550600wrd.26 - gsmtp')

Answer 1

Your code can be shortened down to just two lines:

import smtplib
mailServer = smtplib.SMTP("smtp.gmail.com", 465)

And if you get smtplib.SMTPServerDisconnected, this means that your question is not about the code. Something is blocking your network connection to port 465.

Answer 2

A SMTP server on port 465 is listening for encrypted TLS connections. The client is not supposed to start the encryption with STARTTLS, because TLS is active from the beginning. That SMTP command is used on port 587 where SMTP servers are listening for plaintext connections.

Answer 3

you can use flask_mail library for sending mail.Here is just quick review.. '

from flask_mail import Mail, Message
app.config['SECRET_KEY'] = 'your secretkey'
app.config['MAIL_SERVER'] = 'smtp.gmail.com'
app.config['MAIL_PORT'] = 465
app.config['MAIL_USE_TLS'] = False
app.config['MAIL_USE_SSL'] = True
app.config['MAIL_USERNAME'] = 'your gmail id'
app.config['MAIL_PASSWORD'] = 'and its password'
mail = Mail(app)
msg = Message(subject=subject, sender=(master().user(), 
app.config['MAIL_USERNAME']), recipients=[recipients])
msg.body = "%s %s" % (body, msg.sender)
if html is not None:
    msg.html = str(html)
mail.connect()
mail.send(msg)

'

***Note :- do not forget to turn off 2-step verification and also turn on Allow less secure apps from sign-in & security > device activity & security events