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Sending email with python. Google disables less secure apps

I am trying to send email using python. My code was working fine before Google disabled 'less secure apps'. My email address and password are both correct.
server = smtplib.SMTP_SSL("smtp.gmail.com", 465)
serverEmail = "EMAILADDRESS"
serverPw = "QWERTY"
server.login(serverEmail, serverPw)
subject = "Rejection"
body = "Hi! You've been unfortunately declined access to our system."
message = f'Subject: {subject}\n\n{body}'
server.sendmail("EMAILADDRESS", doctorEmail['email'], message)
server.quit()
I get this error now:
smtplib.SMTPAuthenticationError: (535, b'5.7.8 Username and Password not accepted.
I get this error when i use server.starttls():
smtplib.SMTPNotSupportedError: STARTTLS extension not supported by server.

2-step verification turn on then head over to App password
After is generated passwords
import smtplib
with smtplib.SMTP_SSL('smtp.gmail.com', 465) as connection:
email_address = 'your_email_sender#gmail.com'
email_password = 'App_Passwords_is_generated'
connection.login(email_address, email_password )
connection.sendmail(from_addr=email_address, to_addrs='receiver_email#something.com',
msg="subject:hi \n\n this is my message")

This is working for me. You need to generate an app password for this. See https://support.google.com/accounts/answer/185833?hl=en
import smtplib as smtp
connection = smtp.SMTP_SSL('smtp.gmail.com', 465)
email_addr = 'my_email#gmail.com'
email_passwd = 'app_password_generated_in_Google_Account_Settings'
connection.login(email_addr, email_passwd)
connection.sendmail(from_addr=email_addr, to_addrs='recipient#something.com', msg="Sent from my IDE. Hehe")
connection.close()
For some reason, all of my emails are ending up in SPAM folder of the recipient account though.

Google disabled access for 'less secure apps' for a time on June 2, but around 7 PM US Eastern Time they re-enabled it. So if you just waited a few hours, you didn't have to do anything.
I suspect that somehow they got smacked with the 'law of unintended consequences' but it won't surprise me if they turn this access off again at some point.

Why is gmail rejecting my SMTP connection?

I set my gmail account to allow "Less secure apps access" and I use server.starttls() in smtplib in python to make sure the session is encrypted so why is google still periodically rejecting my login with "Please log in via your web browser and then try again. Learn more at https://support.google.com/mail/answer/78754 "
server = smtplib.SMTP(GMAIL_SERVER, GMAIL_PORT)
server.ehlo()
server.starttls()
server.login(GMAIL_USER, GMAIL_PASS)
server.sendmail(GMAIL_USER, [to_address], mime_msg.as_string())
server.close()
logger.info("Email successfully sent")

When using the Gmail SMTP from a programming a lot of times you will get an error with it rejecting your login. It wants you to use the browser using Xoauth2.
A alternative would be to try and use an apps password infested of your true password. In my experience this tends to fix the issue, its often the case when the user has 2fa enabled.

Using proxy on Python SMTP

I want to try hiding my main IP and send email using Hotmail SMTP via Python SMTP Lib. I'm using the following code to send email but its sent from my IP (Originally it sends from Hotmail SMTP but it still shows my IP in the header if can see).
import smtplib
SMTP = "smtp.live.com"
s = smtplib.SMTP(SMTP,587)
s.ehlo()
s.starttls()
s.ehlo()
s.login("username#hotmail.com", "Password")
s.sendmail("username#hotmail.com", "recipient#hotmail.com","Hello World")
Let me know if there's any thing possible from which I can hide my IP and use the proxy IP to send the email. Furthermore, I think playing with socket/socks library might do the trick but still unsure.
Thank you very much.

Sending an email using Python

I'm trying to send myself an email using Python's smtplib module. Here's the code I'm trying to execute:
import smtplib
sender = 'manas.oid#gmail.com'
receivers = ['manas.oid#gmail.com']
message = """From: From Person <manas.oid#gmail.com>
To: To Person <manas.oid#gmail.com>
Subject: SMTP e-mail test
This is a test e-mail message.
"""
try:
smtpObj = smtplib.SMTP('smtp.gmail.com', 587)
smtpObj.sendmail(sender, receivers, message)
print "Successfully sent email"
except smtplib.SMTPException:
print "Error: unable to send email"
However, I get a 'Error:unable to send email' message when I try to execute this script. What seems to be wrong with my script?

You did not login and you did not start the connection with smtpObj.starttls().

To add on to what #Malik says, below are the steps you need to perform before you'll be able to do anything with GMail (provided less secure apps can access your account, see below).
conn = SMTP('smtp.gmail.com',587)
conn.ehlo()
conn.starttls()
conn.ehlo()
conn.login(username,pwd)
conn.sendmail(username, emailID, message)
Note that after recent changes to GMail, you'll need to explicitly allow less secure apps to access your account. GMail would block your request to login until you enable it. Link to enable less secure apps to access: https://support.google.com/accounts/answer/6010255?hl=en

Gmail wouldn't let you send an unauthenticated email from an account.
Instead, use the Gmail API to send emails. Some useful links below:
Authentication: https://developers.google.com/gmail/api/auth/web-server
Email: https://developers.google.com/gmail/api/guides/sending

Sending an email via gmail through a python application

as indicated by the title I am having trouble sending an email via my gmail account through a python application.I have searched online for a solution but nothing seems to solve it and I thought I might ask here.
My code is the following:
FROMADDR = "myemail#gmail.com"
LOGIN = FROMADDR
PASSWORD = "mypass"
TOADDRS = "varis81#hotmail.com"
msg = "Test message"
server = smtplib.SMTP('smtp.gmail.com', 587)
server.set_debuglevel(1)
server.ehlo()
server.starttls()
server.login(LOGIN, PASSWORD)
server.sendmail(FROMADDR, TOADDRS, msg)
server.quit()
print "E-mail succesfully sent"
I get the message:
socket.error: [Errno 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 tried different ports but it doesn't work also.I also tried hotmail but it causes the same problem.I am using Python 2.7 (don't ask :) ) on a Windows 7 machine developing on Eclipse using PyDev.
Any help would be great!
Thank you in advance.

I'm using the same construct on one of my servers. My code is below.
The only difference is the extra .ehlo() after '.starttls()`. This should not be the issue; from the RFC:
5.2 Result of the STARTTLS Command
The client SHOULD send an EHLO command as the first
command after a successful TLS negotiation.
According to the RFC, the server should not sever a connection if the client does not send ehlo after starttls, but Google could be more restrictive on their SMTP server. I'd check that first. (I've seen providers tighten down on these kinds of conditions to reduce spam, see Mailinator's 2007 writeup for instance.)
It could also be filtered ports - try running the code in the REPL and confirm which line is exceptioning, if it's the connect() you'll know it's network. If it's after, it's likely your usage of smtplib.
Of note, I also experienced occasional unclean shutdowns, resulting in the try/except around .close().
import smtplib
s = smtplib.SMTP()
s.connect("smtp.gmail.com")
s.ehlo()
s.starttls()
s.ehlo()
s.login("from#gmail.com", "frompass")
s.sendmail("fromname#gmail.com", toAddr, bytes)
try:
s.close()
except: pass

Well, since I cant post comments yet I'll have to attempt an answer..
Judging by this: Python SMTP Errno 10060
Perhaps a timeout would help?