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python 3.9.0 smtplib.SMTPNotSupportedError: STARTTLS extension not supported by server

I am trying to send emails with gmail using the smtp module for an amazon price tracker. A few days ago, it was working perfectly but today it came up with this error:
File "C:\Users\61409\AppData\Local\Programs\Python\Python39\lib\smtplib.py", line 755, in starttls
raise SMTPNotSupportedError(
smtplib.SMTPNotSupportedError: STARTTLS extension not supported by server.
This is the code that originally worked but gives the error:
import smtplib
def send_email():
server = smtplib.SMTP('smtp.gmail.com', 587)
server.ehlo()
server.starttls()
server.ehlo()
server.login('xxxxxxxx#gmail.com', '*password*')
subject = f'The price of your product has fallen'
body = f'Check the amazon link - {URL}'
msg = f"Subject: {subject}\n\n{body}"
server.sendmail(
'xxxxxxx#gmail.com',
'xxxxxxx#gmail.com',
msg
)
print('The email has been sent')
server.quit()
I have tried making another gmail account and using SSL (importing ssl too) but the other gmail account comes up with the same problem and when using SSL, it comes up with a SMTP AUTH problem (unable to solve this too). I have allowed less secure apps but the same problem still occurs. I have also tried removing the first server.ehlo() and I have also tried using the server.set_debuglevel(1) but both do not work. I have also tried using with stmplib.SMTP(*Host*, *Port*) as server: and I have tried just using SMTP without using SSl and TLS at all but both answers do not work. Most of the answers removed the smtplib.SMTPNotSupportedError: STARTTLS extension not supported by server. but other problems occured such as smtplib.SMTPServerDisconnected: Connection unexpectedly closed which happened numerous times with other answers. I tried researching on solutions to the connection unexpectedly closing but none of those answers worked too.
These are the answers I have tried:
SMTPException: STARTTLS extension not supported by server
smtplib.SMTPNotSupportedError: STARTTLS extension not supported by server
Python 2: SMTPServerDisconnected: Connection unexpectedly closed
Python3 SMTP 'Connection unexpectedly closed'
https://www.reddit.com/r/Python/comments/5grxy8/python_smtplib_connection_unexpectedly_closed/daumi2m/
How to send an email with Python?
How can I fix this problem?, am I missing something?? Will I need to use another module or library to send emails??? I apologise if this is a repeat question with a viable answer. I also apologise if one of the answers I mentioned as not working does actual work except I screwed up the code.

smtplib.SMTPNotSupportedError: STARTTLS extension not supported by server.
The SMTP connection to the server does not seem to offer the STARTTLS extension, at least as seen from the perspective of the client. This extension is announced inside the response to the initial EHLO command of the client:
$ telnet smtp.gmail.com 587
...
Connected to smtp.gmail.com.
Escape character is '^]'.
220 smtp.gmail.com ESMTP h9sm19557267wre.24 - gsmtp
EHLO mail.example.com
250-smtp.gmail.com at your service, ...
250-SIZE 35882577
250-8BITMIME
250-STARTTLS <<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<
...
Given that smtp.gmail.com definitely supports this extension it is likely that there is some man in the middle somewhere in path of the connection, which rewrites the traffic to something like this:
220 smtp.gmail.com ESMTP h9sm19557267wre.24 - gsmtp
EHLO mail.example.com
250-smtp.gmail.com at your service, ...
250-SIZE 35882577
250-8BITMIME
250-XXXXXXXA <<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<
...
Here the response of the server is changed to no longer show support for STARTTLS, in the hope that the client continues without encryption and thus the mail can be analyzed be the man in the middle. Such man in the middle are typically corporate firewalls like Cisco ASA but can also be ISP or local antivirus products.
A few days ago, it was working perfectly but today it came up with this error:
Check if there were any changes regarding local security products (antivirus) or its settings or if there are changes to your environment (corporate firewall, different network you use ...).

I had the same problem: smtplib working properly and then returning this same error, without any change in the server (outlook).
It just so happens that I had refactored my code, and the function that sent the email was deeper in the modules.
If I used the old way, it worked!
When I turned off the anti-virus (AVG in my case), all worked just fine!
So, for some reason, the code refactoring made the sending procedure to be caught by anti-virus.

SMTP Authentication Error had occured. How to resolve that?

Code is provided below:
import smtplib
s=smtplib.SMTP('127.0.0.1',587)
s.starttls()
s.login("EMAIL_ADDRESS#gmail.com","PASSWORD")
messsage="congrats"
s.sendmail('EMAIL_ADDRESS#gmail.com','RECIPIENT_ADDRESS#gmail.com',message)
s.quit()
Error:
SMTPAuthenticationError:
(535, b'5.7.8 Username and Password not accepted.

The SMTP server should be smtp.gmail.com, not 127.0.0.1. 127.0.0.1 refers to localhost or the current server you are running on. So unless you happen to be running on Gmail's SMTP server, this will not work as you currently have it. Of course, you must also use a correct email/password combination.

Send mail with smtplib using proxy

I have a very basic piece of Python code:
import smtplib
server = smtplib.SMTP(host, port)
problems = server.sendmail(from_addr, to_addr, message)
Is there solution to run it behind an HTTP proxy? I am using Python 3.4.1 on Linux with the http_proxy variable set.
Now I am getting a timeout from SMTP, but if I run this code from a proxy-free network, it works OK.

Is there solution to run it behind an HTTP proxy?
No, HTTP is a different protocol than SMTP and the proxy is for HTTP only. If you are very lucky you might be able to create a tunnel using the CONNECT command to the outside SMTP server, but usually the ports used for CONNECT are restricted so that you will not be able to create a tunnel to an outside host port 25 (i.e. SMTP).

Connect to SMTP (SSL or TLS) using Python

I am attempting to connect to the Gmail SMTP mail server and perform tasks as outlined by the skeleton code given to me. Only the use of sockets is allowed (so not the smtplib). I need to: send HELO command, MAIL FROM, RCPT TO, and DATA.
There are many cases of similar problems posted, but they haven't received the proper answer. For example:
Implementing Transport Layer Security in Python - Simple Mail Client
The program is required to connect to smtp.gmail.com over port 587. I've taken two different approaches:
Using STARTTLS:
mailserver = 'smtp.gmail.com'
clientSocket = socket(AF_INET, SOCK_STREAM)
clientSocket.connect((mailserver, 587))
recv = clientSocket.recv(1024)
print recv
if recv[:3] != '220':
print '220 reply not received from server.'
#Send HELO command and print server response
heloCommand = 'HELO Alice\r\n'
clientSocket.send(heloCommand)
recv1 = clientSocket.recv(1024)
print recv1
if recv1[:3] != '250':
print '250 reply not received from server.'
#Send MAIL FROM command and print server response.
command = "STARTTLS\r\n"
clientSocket.send(command)
recvdiscard = clientSocket.recv(1024)
print recvdiscard
clientSocket.send("MAIL From: email\r\n")
recv2 = clientSocket.recv(1024)
print recv2
if recv2[:3] != '250':
print '250 reply not received from server.'
Using SSL:
clientSocketSSL = ssl.wrap_socket(clientSocket)
Then clientSocketSSL replaces all instances of clientSocket. The STARTTLS lines are also removed and import ssl is added to the top.
When using the first method, the MAIL FROM: command isn't returning anything. I'm getting the following output:
250 mx.google.com at your service
220 2.0.0 Ready to start TLS
250 reply not received from server.
When using SSL, I'm getting the same as the linked post:
ssl.SSLError: [Errno 1] _ssl.c:504: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol
Am I missing something here? I guess my best option is to use TLS but I have no idea how to go about that... is there something wrong with my MAIL FROM command?

When using SSL, you need to connect to port 465 instead of port 587. If you use STARTTLS, you still need to use ssl.wrap_socket, you just do it later - specifically, after receiving the 220 response to the STARTTLS command. After doing STARTTLS, you're supposed to do HELO again, since the server is supposed to forget anything that happened before the STARTTLS.
In either case, the servers at smtp.google.com ports 465 and 587 still won't return a 250 response to the MAIL command, since they require that you are authenticated before you send mail. You'll get a 530 response instead. You'll need to use the AUTH command with your gmail.com credentials to authenticate before you can use MAIL successfully on those servers.
If you don't want to authenticate, and depending on the details of what you need to do, you could try using port 25 of the server found in gmail.com's MX record. At the moment, the server is gmail-smtp-in.l.google.com and supports STARTTLS.

After STARTTLS, call
clientSocket = ssl.wrap_socket(clientSocket)

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?