def send_email(user, pwd, recipient, subject, body):
 import smtplib
 FROM = user
 TO = recipient if isinstance(recipient, list) else [recipient]
 SUBJECT = subject
 TEXT = body
 # Prepare actual message
 message = """From: %s\nTo: %s\nSubject: %s\n\n%s
 """ % (FROM, ", ".join(TO), SUBJECT, TEXT)
 try:
 server = smtplib.SMTP("smtp.gmail.com", 587)
 server.ehlo()
 server.starttls()
 server.login(user, pwd)
 server.sendmail(FROM, TO, message)
 server.close()
 print 'successfully sent the mail'
 except:
 print "failed to send mail"

if you want to use Port 465 you have to create an SMTP_SSL object:

# SMTP_SSL Example
server_ssl = smtplib.SMTP_SSL("smtp.gmail.com", 465)
server_ssl.ehlo() # optional, called by login()
server_ssl.login(gmail_user, gmail_pwd) 
# ssl server doesn't support or need tls, so don't call server_ssl.starttls() 
server_ssl.sendmail(FROM, TO, message)
#server_ssl.quit()
server_ssl.close()
print 'successfully sent the mail'

You need to say EHLO before just running straight into STARTTLS:

server = smtplib.SMTP('smtp.gmail.com:587')
server.ehlo()
server.starttls()

Also you should really create From:, To: and Subject: message headers, separated from the message body by a blank line and use CRLF as EOL markers.

E.g.

msg = "\r\n".join([
 "From: [email protected]",
 "To: [email protected]",
 "Subject: Just a message",
 "",
 "Why, oh why"
 ])

Note:

In order for this to work you need to enable "Allow less secure apps" option in your gmail account configuration. Otherwise you will get a "critical security alert" when gmail detects that a non-Google apps is trying to login your account.

As of 2024, this is what works:

Go to https://myaccount.google.com/security and make sure 2-step verification in enabled on your account. So for this you can setup an app on your phone like Google Authenticator, authy etc..

Once you have setup "2-Step Verification", from security go to "2-Step verification" again and scroll down to "App Passwords":

enter image description here

Now give your app a name and you will be given a password for your device.

Finally save your password somewhere safe and plugin your email and password into the following script:

import smtplib
YOUR_GOOGLE_EMAIL = '<[email protected]>' # The email you setup to send the email using app password
YOUR_GOOGLE_EMAIL_APP_PASSWORD = '<your-app-password>' # The app password you generated
smtpserver = smtplib.SMTP_SSL('smtp.gmail.com', 465)
smtpserver.ehlo()
smtpserver.login(YOUR_GOOGLE_EMAIL, YOUR_GOOGLE_EMAIL_APP_PASSWORD)
# Test send mail
sent_from = YOUR_GOOGLE_EMAIL
sent_to = sent_from # Send it to self (as test)
email_text = 'This is a test'
smtpserver.sendmail(sent_from, sent_to, email_text)
# Close the connection
smtpserver.close()

For more details see Google Auth Passwords.

OLD Answer: (This no longer works) I ran into a similar problem and stumbled on this question. I got an SMTP Authentication Error but my user name / pass was correct. Here is what fixed it. I read this:

https://support.google.com/accounts/answer/6010255

In a nutshell, google is not allowing you to log in via smtplib because it has flagged this sort of login as "less secure", so what you have to do is go to this link while you're logged in to your google account, and allow the access:

https://www.google.com/settings/security/lesssecureapps

Once that is set (see my screenshot below), it should work.

enter image description here

Login now works:

smtpserver = smtplib.SMTP("smtp.gmail.com", 587)
smtpserver.ehlo()
smtpserver.starttls()
smtpserver.ehlo()
smtpserver.login('[email protected]', 'me_pass')

Response after change:

(235, '2.7.0 Accepted')

Response prior:

smtplib.SMTPAuthenticationError: (535, '5.7.8 Username and Password not accepted. Learn more at\n5.7.8 http://support.google.com/mail/bin/answer.py?answer=14257 g66sm2224117qgf.37 - gsmtp')

Still not working? If you still get the SMTPAuthenticationError but now the code is 534, its because the location is unknown. Follow this link:

https://accounts.google.com/DisplayUnlockCaptcha

Click continue and this should give you 10 minutes for registering your new app. So proceed to doing another login attempt now and it should work.

UPDATE: This doesn't seem to work right away you may be stuck for a while getting this error in smptlib:

235 == 'Authentication successful'
503 == 'Error: already authenticated'

The message says to use the browser to sign in:

SMTPAuthenticationError: (534, '5.7.9 Please log in with your web browser and then try again. Learn more at\n5.7.9 https://support.google.com/mail/bin/answer.py?answer=78754 qo11sm4014232igb.17 - gsmtp')

After enabling 'lesssecureapps', go for a coffee, come back, and try the 'DisplayUnlockCaptcha' link again. From user experience, it may take up to an hour for the change to kick in. Then try the sign-in process again.

You many now also need create an app password by following the steps under section "Create & use app passwords" here: support.google.com/accounts/answer/185833

This Works

Create Gmail APP Password!

After you create that then create a file called sendgmail.py

Then add this code:

#!/usr/bin/env python3
# -*- coding: utf-8 -*-
# =============================================================================
# Created By : Jeromie Kirchoff
# Created Date: Mon Aug 02 17:46:00 PDT 2018
# =============================================================================
# Imports
# =============================================================================
import smtplib
# =============================================================================
# SET EMAIL LOGIN REQUIREMENTS
# =============================================================================
gmail_user = '[email protected]'
gmail_app_password = 'YOUR-GOOGLE-APPLICATION-PASSWORD!!!!'
# =============================================================================
# SET THE INFO ABOUT THE SAID EMAIL
# =============================================================================
sent_from = gmail_user
sent_to = ['[email protected]', '[email protected]']
sent_subject = "Hey Friends!"
sent_body = ("Hey, what's up? friend!\n\n"
 "I hope you have been well!\n"
 "\n"
 "Cheers,\n"
 "Jay\n")
email_text = """\
From: %s
To: %s
Subject: %s
%s
""" % (sent_from, ", ".join(sent_to), sent_subject, sent_body)
# =============================================================================
# SEND EMAIL OR DIE TRYING!!!
# Details: http://www.samlogic.net/articles/smtp-commands-reference.htm
# =============================================================================
try:
 server = smtplib.SMTP_SSL('smtp.gmail.com', 465)
 server.ehlo()
 server.login(gmail_user, gmail_app_password)
 server.sendmail(sent_from, sent_to, email_text)
 server.close()
 print('Email sent!')
except Exception as exception:
 print("Error: %s!\n\n" % exception)

So, if you are successful, will see an image like this:

I tested by sending an email from and to myself.

Successful email sent.

Note: I have 2-Step Verification enabled on my account. App Password works with this! (for gmail smtp setup, you must go to https://support.google.com/accounts/answer/185833?hl=en and follow the below steps)

This setting is not available for accounts with 2-Step Verification enabled. Such accounts require an application-specific password for less secure apps access.

Less secure app access... This setting is not available for accounts with 2-Step Verification enabled.

Clarification

Navigate to https://myaccount.google.com/apppasswords and create an APP Password as stated above.

https://myaccount.google.com/apppasswords

Here is a Gmail API example. Although more complicated, this is the only method I found that works in 2019. This example was taken and modified from:

https://developers.google.com/gmail/api/guides/sending

You'll need create a project with Google's API interfaces through their website. Next you'll need to enable the GMAIL API for your app. Create credentials and then download those creds, save it as credentials.json.

import pickle
import os.path
from googleapiclient.discovery import build
from google_auth_oauthlib.flow import InstalledAppFlow
from google.auth.transport.requests import Request
from email.mime.text import MIMEText
import base64
#pip install --upgrade google-api-python-client google-auth-httplib2 google-auth-oauthlib
# If modifying these scopes, delete the file token.pickle.
SCOPES = ['https://www.googleapis.com/auth/gmail.readonly', 'https://www.googleapis.com/auth/gmail.send']
def create_message(sender, to, subject, msg):
 message = MIMEText(msg)
 message['to'] = to
 message['from'] = sender
 message['subject'] = subject
 # Base 64 encode
 b64_bytes = base64.urlsafe_b64encode(message.as_bytes())
 b64_string = b64_bytes.decode()
 return {'raw': b64_string}
 #return {'raw': base64.urlsafe_b64encode(message.as_string())}
def send_message(service, user_id, message):
 #try:
 message = (service.users().messages().send(userId=user_id, body=message).execute())
 print( 'Message Id: %s' % message['id'] )
 return message
 #except errors.HttpError, error:print( 'An error occurred: %s' % error )
def main():
 """Shows basic usage of the Gmail API.
 Lists the user's Gmail labels.
 """
 creds = None
 # The file token.pickle stores the user's access and refresh tokens, and is
 # created automatically when the authorization flow completes for the first
 # time.
 if os.path.exists('token.pickle'):
 with open('token.pickle', 'rb') as token:
 creds = pickle.load(token)
 # If there are no (valid) credentials available, let the user log in.
 if not creds or not creds.valid:
 if creds and creds.expired and creds.refresh_token:
 creds.refresh(Request())
 else:
 flow = InstalledAppFlow.from_client_secrets_file(
 'credentials.json', SCOPES)
 creds = flow.run_local_server(port=0)
 # Save the credentials for the next run
 with open('token.pickle', 'wb') as token:
 pickle.dump(creds, token)
 service = build('gmail', 'v1', credentials=creds)
 # Example read operation
 results = service.users().labels().list(userId='me').execute()
 labels = results.get('labels', [])
 if not labels:
 print('No labels found.')
 else:
 print('Labels:')
 for label in labels:
 print(label['name'])
 # Example write
 msg = create_message("[email protected]", "[email protected]", "Subject", "Msg")
 send_message( service, 'me', msg)
if __name__ == '__main__':
 main()

You down with OOP?

#!/usr/bin/env python
import smtplib
class Gmail(object):
 def __init__(self, email, password):
 self.email = email
 self.password = password
 self.server = 'smtp.gmail.com'
 self.port = 587
 session = smtplib.SMTP(self.server, self.port) 
 session.ehlo()
 session.starttls()
 session.ehlo
 session.login(self.email, self.password)
 self.session = session
 def send_message(self, subject, body):
 ''' This must be removed '''
 headers = [
 "From: " + self.email,
 "Subject: " + subject,
 "To: " + self.email,
 "MIME-Version: 1.0",
 "Content-Type: text/html"]
 headers = "\r\n".join(headers)
 self.session.sendmail(
 self.email,
 self.email,
 headers + "\r\n\r\n" + body)
gm = Gmail('Your Email', 'Password')
gm.send_message('Subject', 'Message')

Not directly related but still worth pointing out is that my package tries to make sending gmail messages really quick and painless. It also tries to maintain a list of errors and tries to point to the solution immediately.

It would literally only need this code to do exactly what you wrote:

import yagmail
yag = yagmail.SMTP('[email protected]')
yag.send('[email protected]', 'Why,Oh why!')

Or a one liner:

yagmail.SMTP('[email protected]').send('[email protected]', 'Why,Oh why!')

For the package/installation please look at git or pip, available for both Python 2 and 3.

You can find it here: http://jayrambhia.com/blog/send-emails-using-python

smtp_host = 'smtp.gmail.com'
smtp_port = 587
server = smtplib.SMTP()
server.connect(smtp_host,smtp_port)
server.ehlo()
server.starttls()
server.login(user,passw)
fromaddr = raw_input('Send mail by the name of: ')
tolist = raw_input('To: ').split()
sub = raw_input('Subject: ')
msg = email.MIMEMultipart.MIMEMultipart()
msg['From'] = fromaddr
msg['To'] = email.Utils.COMMASPACE.join(tolist)
msg['Subject'] = sub 
msg.attach(MIMEText(raw_input('Body: ')))
msg.attach(MIMEText('\nsent via python', 'plain'))
server.sendmail(user,tolist,msg.as_string())

Dec, 2022 Update:

You need to use an app password to allow your app to access your google account.

Sign in with App Passwords:

An App Password is a 16-digit passcode that gives a less secure app or device permission to access your Google Account. App Passwords can only be used with accounts that have 2-Step Verification turned on.

In addition, google hasn't allowed your app to access your google account with username(email address) and password since May 30, 2022. So now, you need username(email address) and an app password to access your google account.

Less secure apps & your Google Account:

To help keep your account secure, from May 30, 2022, ​​Google no longer supports the use of third-party apps or devices which ask you to sign in to your Google Account using only your username and password.

How to generate an app password:

First, click on Account from 9 dots:

enter image description here

Then, click on App passwords from Security. *Don't forget to turn on 2-Step Verification before generating an app password otherwise you cannot generate an app password:

enter image description here

Then, click on Other (Custom name):

enter image description here

Then, put your app name, then click on GENERATE:

enter image description here

Finally, you could generate the app password xylnudjdiwpojwzm:

enter image description here

So, your code with the app password above is as shown below:

import smtplib
fromaddr = '[email protected]'
toaddrs = '[email protected]'
msg = 'Why,Oh why!'
username = '[email protected]'
password = 'xylnudjdiwpojwzm' # Here
server = smtplib.SMTP('smtp.gmail.com:587')
server.starttls()
server.login(username,password)
server.sendmail(fromaddr, toaddrs, msg)
server.quit()

In addition, settings.py with the app password above in Django is as shown below:

# "settings.py"
EMAIL_BACKEND = 'django.core.mail.backends.smtp.EmailBackend'
EMAIL_HOST = 'smtp.gmail.com'
EMAIL_PORT = 587
EMAIL_USE_TLS = True
EMAIL_HOST_USER = '[email protected]'
EMAIL_HOST_PASSWORD = 'xylnudjdiwpojwzm' # Here

Realized how painful many of the things are with sending emails via Python thus I made an extensive library for it. It also has Gmail pre-configured (so you don't have to remember Gmail's host and port):

from redmail import gmail
gmail.user_name = "[email protected]"
gmail.password = "<YOUR APPLICATION PASSWORD>"
# Send an email
gmail.send(
 subject="An example email",
 receivers=["[email protected]"],
 text="Hi, this is text body.",
 html="<h1>Hi, this is HTML body.</h1>"
)

Of course you need to configure your Gmail account (don't worry, it's simple):

1. Set up 2-step-verification (if not yet set up)
2. Create an Application password
3. Put the Application password to the gmail object and done!

Red Mail is actually pretty extensive (include attachments, embed images, send with cc and bcc, template with Jinja etc.) and should hopefully be all you need from an email sender. It is also well tested and documented. I hope you find it useful.

To install:

pip install redmail

Documentation: https://red-mail.readthedocs.io/en/latest/

Source code: https://github.com/Miksus/red-mail

Note that Gmail don't allow changing the sender. The sender address is always you.

Enable less secure apps on your gmail account and use (Python>=3.6):

import smtplib
from email.mime.multipart import MIMEMultipart
from email.mime.text import MIMEText
gmailUser = '[email protected]'
gmailPassword = 'XXXXX'
recipient = '[email protected]'
message = f"""
Type your message here...
"""
msg = MIMEMultipart()
msg['From'] = f'"Your Name" <{gmailUser}>'
msg['To'] = recipient
msg['Subject'] = "Subject here..."
msg.attach(MIMEText(message))
try:
 mailServer = smtplib.SMTP('smtp.gmail.com', 587)
 mailServer.ehlo()
 mailServer.starttls()
 mailServer.ehlo()
 mailServer.login(gmailUser, gmailPassword)
 mailServer.sendmail(gmailUser, recipient, msg.as_string())
 mailServer.close()
 print ('Email sent!')
except:
 print ('Something went wrong...')

There is a gmail API now, which lets you send email, read email and create drafts via REST. Unlike the SMTP calls, it is non-blocking which can be a good thing for thread-based webservers sending email in the request thread (like python webservers). The API is also quite powerful.

• Of course, email should be handed off to a non-webserver queue, but it's nice to have options.

It's easiest to setup if you have Google Apps administrator rights on the domain, because then you can give blanket permission to your client. Otherwise you have to fiddle with OAuth authentication and permission.

Here is a gist demonstrating it:

https://gist.github.com/timrichardson/1154e29174926e462b7a

great answer from @David, here is for Python 3 without the generic try-except:

def send_email(user, password, recipient, subject, body):
 gmail_user = user
 gmail_pwd = password
 FROM = user
 TO = recipient if type(recipient) is list else [recipient]
 SUBJECT = subject
 TEXT = body
 # Prepare actual message
 message = """From: %s\nTo: %s\nSubject: %s\n\n%s
 """ % (FROM, ", ".join(TO), SUBJECT, TEXT)
 server = smtplib.SMTP("smtp.gmail.com", 587)
 server.ehlo()
 server.starttls()
 server.login(gmail_user, gmail_pwd)
 server.sendmail(FROM, TO, message)
 server.close()

Seems like problem of the old smtplib. In python2.7 everything works fine.

Update: Yep, server.ehlo() also could help.

This will help you. I use this method

1. First of all, you must activate "2-step verification" from your Google account. follow the below path:

go to google account -> "security" tab (from left menu) -> find "How you sign in to Google" and then enable "2-step verification"

2. click on "2-step verification" and then click on "App passwords" at the bottom of the page. Then, click on "select app" and chose "other (custom name)". Then, write a name and click on generate.

3. save the password which displays on the screen.enter image description here

4. I used below code, you can confiq and use it.

import os
from email.message import EmailMessage
import ssl
import smtplib
email_sender = '[email protected]' #only gmail
email_password = 'Your password from section 3'
email_receiver = '[email protected]' #any type of email
subject = 'check my website (Mohsennavazani.ir)'
body = """
Hello,
this is a test 
"""
em = EmailMessage()
em['From'] = email_sender
em['To'] = email_receiver
em['Subject'] = subject
em.set_content(body)
#add a layer of security
context = ssl.create_default_context()
#sending the email
with smtplib.SMTP_SSL('smtp.gmail.com', 465, context=context) as smtp: 
 smtp.login(email_sender,email_password)
 smtp.sendmail(email_sender,email_receiver, em.as_string())

5- (optional) if you need to send an email to more that 1 email address, you can use the below code in the last part.

li = ["[email protected]", "[email protected]"] 
with smtplib.SMTP_SSL('smtp.gmail.com',465,context=context) as smtp: 
 smtp.login(email_sender,email_password)
 smtp.sendmail(email_sender,li, em.as_string())

 import smtplib
 fromadd='[email protected]'
 toadd='[email protected]'
 msg='''hi,how r u'''
 username='[email protected]'
 passwd='password'
 try:
 server = smtplib.SMTP('smtp.gmail.com:587')
 server.ehlo()
 server.starttls()
 server.login(username,passwd)
 server.sendmail(fromadd,toadd,msg)
 print("Mail Send Successfully")
 server.quit()
 except:
 print("Error:unable to send mail")
 NOTE:https://www.google.com/settings/security/lesssecureapps that should be enabled

import smtplib
server = smtplib.SMTP('smtp.gmail.com', 587)
server.ehlo()
server.starttls()
server.login("fromaddress", "password")
msg = "HI!"
server.sendmail("fromaddress", "receiveraddress", msg)
server.quit()

• python
• email
• smtp
• gmail
• smtp-auth