SSL error while sending email using smtp with Python - python-3.x

I want to send an email using outlook. The code is as follows:
import smtplib
from email.message import EmailMessage
msg = EmailMessage()
msg['From'] = '*******'
msg['Subject'] = 'Some subject here'
msg['To'] = '********'
msg.set_content('Some text here')
with smtplib.SMTP_SSL('smtp-mail.outlook.com', 587) as smtp:
smtp.login('******', '****')
smtp.send_message(msg)
print('Email sent!')
I get the following error:
---------------------------------------------------------------------------
SSLError Traceback (most recent call last)
<ipython-input-8-4d5956f55c88> in <module>
6 msg.set_content('Some text here')
7
----> 8 with smtplib.SMTP_SSL('smtp-mail.outlook.com', 587) as smtp:
9 smtp.login('sender_email', 'password')
10 smtp.send_message(msg)
~/anaconda/envs/quant2/lib/python3.6/smtplib.py in __init__(self, host, port, local_hostname, keyfile, certfile, timeout, source_address, context)
1029 self.context = context
1030 SMTP.__init__(self, host, port, local_hostname, timeout,
-> 1031 source_address)
1032
1033 def _get_socket(self, host, port, timeout):
~/anaconda/envs/quant2/lib/python3.6/smtplib.py in __init__(self, host, port, local_hostname, timeout, source_address)
249
250 if host:
--> 251 (code, msg) = self.connect(host, port)
252 if code != 220:
253 self.close()
~/anaconda/envs/quant2/lib/python3.6/smtplib.py in connect(self, host, port, source_address)
334 if self.debuglevel > 0:
335 self._print_debug('connect:', (host, port))
--> 336 self.sock = self._get_socket(host, port, self.timeout)
337 self.file = None
338 (code, msg) = self.getreply()
~/anaconda/envs/quant2/lib/python3.6/smtplib.py in _get_socket(self, host, port, timeout)
1037 self.source_address)
1038 new_socket = self.context.wrap_socket(new_socket,
-> 1039 server_hostname=self._host)
1040 return new_socket
1041
~/anaconda/envs/quant2/lib/python3.6/ssl.py in wrap_socket(self, sock, server_side, do_handshake_on_connect, suppress_ragged_eofs, server_hostname, session)
405 suppress_ragged_eofs=suppress_ragged_eofs,
406 server_hostname=server_hostname,
--> 407 _context=self, _session=session)
408
409 def wrap_bio(self, incoming, outgoing, server_side=False,
~/anaconda/envs/quant2/lib/python3.6/ssl.py in __init__(self, sock, keyfile, certfile, server_side, cert_reqs, ssl_version, ca_certs, do_handshake_on_connect, family, type, proto, fileno, suppress_ragged_eofs, npn_protocols, ciphers, server_hostname, _context, _session)
815 # non-blocking
816 raise ValueError("do_handshake_on_connect should not be specified for non-blocking sockets")
--> 817 self.do_handshake()
818
819 except (OSError, ValueError):
~/anaconda/envs/quant2/lib/python3.6/ssl.py in do_handshake(self, block)
1075 if timeout == 0.0 and block:
1076 self.settimeout(None)
-> 1077 self._sslobj.do_handshake()
1078 finally:
1079 self.settimeout(timeout)
~/anaconda/envs/quant2/lib/python3.6/ssl.py in do_handshake(self)
687 def do_handshake(self):
688 """Start the SSL/TLS handshake."""
--> 689 self._sslobj.do_handshake()
690 if self.context.check_hostname:
691 if not self.server_hostname:
SSLError: [SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:852)

Microsoft Outlook uses STARTTLS when sending an email. So you need to replace smtplib.SMTP_SSL with smtplib.SMTP and you need to call starttls
reference: smtplib.SMTP.starttls
import smtplib
from email.message import EmailMessage
sender = 'somename#outlook.com'
recipient = 'somename#gmail.com'
msg = EmailMessage()
msg.set_content('this is a test')
msg['From'] = 'somename#outlook.com'
msg['To'] = 'somename#gmail.com'
msg['Subject'] = 'test email'
with smtplib.SMTP('smtp.office365.com', 587) as server:
server.ehlo()
server.starttls()
server.ehlo()
server.ehlo()
server.login('your_login', "your_password", initial_response_ok=True)
server.ehlo()
server.sendmail(sender, recipient, msg.as_string())
print('Email sent!')
server.close()
Here is the Outlook message in my Gmail account.
I noted that I had to change my Outlook password, because it had a \n, which Python read as a new line.
----------------------------------------
My system information
----------------------------------------
Platform: macOS
OS Version: 10.15.7
Python Version: 3.9
----------------------------------------
Your question didn't identity the type of Outlook account you have.
Free account
Corporate account
You stated in the comments below that your error message included ask your email administrator. I haven't seem this message with the Free account so I'm assuming that you might have a Corporate account. If you do have the latter please review this Enable or disable authenticated client SMTP submission, because an email administrator would need to enable Authenticated SMTP on your corporate account.

The answer from user "Life is complex" is almost right. I would like to add few more things from myside which might help. I am not very sure which python version you are using here. I am guessing it as Python 3.X. You need to go through based on actual version of python you are using in your case.
From Python smtplib documents, link. Please check which python version you are using with below guide line.
class smtplib.SMTP_SSL(host='', port=0, local_hostname=None,
keyfile=None, certfile=None, [timeout, ]context=None,
source_address=None) An SMTP_SSL instance behaves exactly the same as
instances of SMTP. SMTP_SSL should be used for situations where SSL is
required from the beginning of the connection and using starttls() is
not appropriate. If host is not specified, the local host is used. If
port is zero, the standard SMTP-over-SSL port (465) is used. The
optional arguments local_hostname, timeout and source_address have the
same meaning as they do in the SMTP class. context, also optional, can
contain a SSLContext and allows configuring various aspects of the
secure connection. Please read Security considerations for best
practices.
keyfile and certfile are a legacy alternative to context, and can
point to a PEM formatted private key and certificate chain file for
the SSL connection.
Changed in version 3.3: context was added.
Changed in version 3.3: source_address argument was added.
Changed in version 3.4: The class now supports hostname check with
ssl.SSLContext.check_hostname and Server Name Indication (see
ssl.HAS_SNI).
Deprecated since version 3.6: keyfile and certfile are deprecated in
favor of context. Please use ssl.SSLContext.load_cert_chain() instead,
or let ssl.create_default_context() select the system’s trusted CA
certificates for you.
Changed in version 3.9: If the timeout parameter is set to be zero, it
will raise a ValueError to prevent the creation of a non-blocking
socket
You need to check that SSLV3 is enabled at Server end or not. Check out this link to see which client version can connect to which server version SSL Version Compatibility first.
import smtplib
import ssl
context = ssl.SSLContext(ssl.PROTOCOL_TLS)
#Above line is required to switch default SSLV3 protocol to TLS, recommended by python docs
# If you want to use SSLV3 and you are sure that it is enabled on server end then use
#context = ssl.SSLContext(ssl.PROTOCOL_SSLv3)
connection = smtplib.SMTP('smtp-mail.outlook.com', 587)
connection.ehlo()
connection.starttls(context=context)
connection.ehlo()
connection.login('now_your_real_login_data#outlook.com', 'otherwise_SMTPServerDisconnect')

The accepted answer didn't work for me, I kept getting this error:
smtplib.SMTPNotSupportedError: STARTTLS extension not supported by server.
I also tried SMTP_SSL instead of SMTP:
context = ssl.SSLContext(ssl.PROTOCOL_TLS)
with smtplib.SMTP_SSL('smtp-mail.outlook.com', 587, context=context) as server:
server.ehlo()
server.starttls(context=context)
but got this error:
[SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:1131)
Fortunately this post (thanks #dhruv-gami) helped me find my issue.
I found out that my hostname (using WSL on windows) is uppercase, but Outlook servers do not accept uppercase host names.
The solution is to just add a lowercase string in the ehlo commands:
with smtplib.SMTP('smtp.office365.com', 587) as server:
server.ehlo('lowercase')
server.starttls()
server.ehlo('lowercase')
server.login('your_login', "your_password", initial_response_ok=True)

Related

Unable to Send an email via python- Error- smtplib.SMTPServerDisconnected: Connection unexpectedly closed

port = 465 # For SSL
smtp_server = "smtp.mail.yahoo.com"
sender_email = "c.junction#yahoo.com" # Enter your address
password = input("Type your password and press enter:")
receiver_email = "jawoneb660#jobsfeel.com" # Enter receiver address
Subject = "Hi there"
message = """Hello World!!!
This message is sent from Python."""
context = ssl.create_default_context()
with smtplib.SMTP_SSL(smtp_server, port, context=context) as smtp:
smtp.login(sender_email, password)
smtp.sendmail(sender_email, receiver_email, Subject, message)
I tried checking if there is any auth failure.Email could not be sent. I got following error msg.
raise SMTPServerDisconnected("Connection unexpectedly closed")
smtplib.SMTPServerDisconnected: Connection unexpectedly
closed`
import smtplib ##Import needed modules
import ssl
port = 465 # For SSL
smtp_server = "smtp.mail.yahoo.com"
sender_email = "c.junction#yahoo.com" # Enter your address
password = input("Type your password and press enter:")
receiver_email = "jawoneb660#jobsfeel.com" # Receiver address
Subject = "Hi there"
message = """Hello World!!!
This message is sent from Python."""
context = ssl.create_default_context()
try:
print("Connecting to server...")
yahoo_server = smtplib.SMTP(smtp_server, port)
yahoo_server.starttls(context=context)
yahoo_server.login(sender_email, password)
print("Connected to server!")
print(f"Sending email to - {receiver_email}")
yahoo_server.sendmail(sender_email, receiver_email, Subject, message)
print("Email successfully sent to - {receiver_email}")
except Exception as e:
print(e)
finally:
yahoo_server.quit
I added a couple of modules that I didn't see. But you need those in order to use the ssl methods as well as the smtplib.
I also added a couple of print statements to help with seeing where in the process this might be getting hung up. You also want to close the connection as best practice.
lastly I added a variable to use with the steps of logging into the smtp server. I did this for Gmail recently so I don't know if this will work offhand, but at the very least the print statements and additional variables should hopefully help with that as well.

"Connection unexpectedly closed" error while sending email using SES from AWS

So I'm trying to send an email to my self using SMTP and AWS. The email I'm using on my configuration is verified since I'm still using sandbox mode in SES. While running the script I keep getting the error Connection unexpectedly closed even dough I tried to connect with OpenSSL and it connected but it showed a Didn't find STARTTLS in server response, trying anyway... error after connecting.
Here is my code:
MAIL = {}
MAIL['USERNAME'] = 'AKIAXARHTFGFKCDAO7PD'
MAIL['PASSWORD'] = 'BE0tXPq8wteiKZYtgD2TgtfFTGhgFGOhUp3F0lG0uqn'
MAIL['HOST'] = 'email-smtp.eu-central-1.amazonaws.com'
MAIL['PORT'] = 465
# Set user code
code = random.randrange(000000, 999999)
# Send email to user
print(code)
print(current_user.email)
msg = MIMEMultipart('alternative')
msg['Subject'] = 'Ruby - Verification code'
msg['From'] = 'amng835#gmail.com'
msg['To'] = current_user.email
msg.attach(MIMEText(f'Your verification code is: {code}', 'plain'))
try:
server = smtplib.SMTP(MAIL['HOST'], MAIL['PORT'])
server.ehlo()
server.starttls()
server.ehlo()
server.login(MAIL('MAIL_USERNAME'), MAIL('MAIL_PASSWORD'))
server.sendmail('amng835#gmail.com', current_user.email, msg.as_string())
server.close()
except Exception as error:
print('Failed to send message to user')
print(error)
OpenSSL output:
The command:
openssl s_client -connect email-smtp.eu-central-1.amazonaws.com:465 -starttls smtp
The output:
CONNECTED(00000005)
Didn't find STARTTLS in server response, trying anyway...
write:errno=0
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 0 bytes and written 372 bytes
Verification: OK
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
Early data was not sent
Verify return code: 0 (ok)
---
My documentation source:
https://docs.aws.amazon.com/ses/latest/DeveloperGuide/examples-send-using-smtp.html
There seems to have some issue with port 465.Change the code to below and it will work fine.
MAIL['PORT'] = 587

Issue when trying to send emails through Python

OS: MacCatalinva V10.15.3
Python: 3.7.7
PiP: 20.0.2
Hey,
I'm new to coding so I'm not sure what this really means.
I'm trying to send emails via Python through Gmail, I've set my account to accept "Less secure app access" and followed the steps in this guide, but all I get is the following:
`[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: unable to get local issuer certificate (_ssl.c:1076)
Traceback (most recent call last):
File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/smtplib.py", line 354, in send
self.sock.sendall(s)
OSError: [Errno 9] Bad file descriptor
During handling of the above exception, another exception occurred:
Traceback (most recent call last):
File "/Users/mymac/Desktop/Test2.py", line 34, in
server.quit()
File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/smtplib.py", line 984, in quit
res = self.docmd("quit")
File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/smtplib.py", line 420, in docmd
self.putcmd(cmd, args)
File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/smtplib.py", line 367, in putcmd
self.send(str)
File "/Library/Frameworks/Python.framework/Versions/3.7/lib/python3.7/smtplib.py", line 357, in send
raise SMTPServerDisconnected('Server not connected')
smtplib.SMTPServerDisconnected: Server not connected`
And this is my Code:
import smtplib
import ssl
sender_email = "myemailadress#gmail.com"
receiver_email = "myadress#hotmail.com"
message = """\
Subject: Hi there
This message is sent from Python."""
# Send email here
smtp_server = "smtp.gmail.com"
port = 587 # For starttls
sender_email = "myemailadress#gmail.com"
password = input("Type your password and press enter: ")
# Create a secure SSL context
context = ssl.create_default_context()
# Try to log in to server and send email
try:
server = smtplib.SMTP(smtp_server, port)
server.ehlo() # Can be omitted
server.starttls(context=context) # Secure the connection
server.ehlo() # Can be omitted
server.login(sender_email, password)
# TODO: Send email here
except Exception as e:
# Print any error messages to stdout
print(e)
finally:
server.quit()
1)After this line:
server.login(sender_email, password)
make sure to send the message you have it.
For that:
server.sendmail(sender_email,receiver_email,message)
that's it, I hope.

Python module that will handle connections and add in a Proxy? [duplicate]

I'd like to manually (using the socket and ssl modules) make an HTTPS request through a proxy which itself uses HTTPS.
I can perform the initial CONNECT exchange just fine:
import ssl, socket
PROXY_ADDR = ("proxy-addr", 443)
CONNECT = "CONNECT example.com:443 HTTP/1.1\r\n\r\n"
sock = socket.create_connection(PROXY_ADDR)
sock = ssl.wrap_socket(sock)
sock.sendall(CONNECT)
s = ""
while s[-4:] != "\r\n\r\n":
s += sock.recv(1)
print repr(s)
The above code prints HTTP/1.1 200 Connection established plus some headers, which is what I expect. So now I should be ready to make the request, e.g.
sock.sendall("GET / HTTP/1.1\r\n\r\n")
but the above code returns
<!DOCTYPE HTML PUBLIC "-//IETF//DTD HTML 2.0//EN">
<html><head>
<title>400 Bad Request</title>
</head><body>
<h1>Bad Request</h1>
<p>Your browser sent a request that this server could not understand.<br />
Reason: You're speaking plain HTTP to an SSL-enabled server port.<br />
Instead use the HTTPS scheme to access this URL, please.<br />
</body></html>
This makes sense too, since I still need to do an SSL handshake with the example.com server to which I'm tunneling. However, if instead of immediately sending the GET request I say
sock = ssl.wrap_socket(sock)
to do the handshake with the remote server, then I get an exception:
Traceback (most recent call last):
File "so_test.py", line 18, in <module>
ssl.wrap_socket(sock)
File "/usr/lib/python2.6/ssl.py", line 350, in wrap_socket
suppress_ragged_eofs=suppress_ragged_eofs)
File "/usr/lib/python2.6/ssl.py", line 118, in __init__
self.do_handshake()
File "/usr/lib/python2.6/ssl.py", line 293, in do_handshake
self._sslobj.do_handshake()
ssl.SSLError: [Errno 1] _ssl.c:480: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol
So how can I do the SSL handshake with the remote example.com server?
EDIT: I'm pretty sure that no additional data is available before my second call to wrap_socket because calling sock.recv(1) blocks indefinitely.
This should work if the CONNECT string is rewritten as follows:
CONNECT = "CONNECT %s:%s HTTP/1.0\r\nConnection: close\r\n\r\n" % (server, port)
Not sure why this works, but maybe it has something to do with the proxy I'm using. Here's an example code:
from OpenSSL import SSL
import socket
def verify_cb(conn, cert, errun, depth, ok):
return True
server = 'mail.google.com'
port = 443
PROXY_ADDR = ("proxy.example.com", 3128)
CONNECT = "CONNECT %s:%s HTTP/1.0\r\nConnection: close\r\n\r\n" % (server, port)
s = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
s.connect(PROXY_ADDR)
s.send(CONNECT)
print s.recv(4096)
ctx = SSL.Context(SSL.SSLv23_METHOD)
ctx.set_verify(SSL.VERIFY_PEER, verify_cb)
ss = SSL.Connection(ctx, s)
ss.set_connect_state()
ss.do_handshake()
cert = ss.get_peer_certificate()
print cert.get_subject()
ss.shutdown()
ss.close()
Note how the socket is first opened and then open socket placed in SSL context. Then I manually initialize SSL handshake. And output:
HTTP/1.1 200 Connection established
<X509Name object '/C=US/ST=California/L=Mountain View/O=Google Inc/CN=mail.google.com'>
It's based on pyOpenSSL because I needed to fetch invalid certificates too and Python built-in ssl module will always try to verify the certificate if it's received.
Judging from the API of the OpenSSL and GnuTLS library, stacking a SSLSocket onto a SSLSocket is actually not straightforwardly possible as they provide special read/write functions to implement the encryption, which they are not able to use themselves when wrapping a pre-existing SSLSocket.
The error is therefore caused by the inner SSLSocket directly reading from the system socket and not from the outer SSLSocket. This ends in sending data not belonging to the outer SSL session, which ends badly and for sure never returns a valid ServerHello.
Concluding from that, I would say there is no simple way to implement what you (and actually myself) would like to accomplish.
Finally I got somewhere expanding on #kravietz and #02strich answers.
Here's the code
import threading
import select
import socket
import ssl
server = 'mail.google.com'
port = 443
PROXY = ("localhost", 4433)
CONNECT = "CONNECT %s:%s HTTP/1.0\r\nConnection: close\r\n\r\n" % (server, port)
class ForwardedSocket(threading.Thread):
def __init__(self, s, **kwargs):
threading.Thread.__init__(self)
self.dest = s
self.oursraw, self.theirsraw = socket.socketpair(socket.AF_UNIX, socket.SOCK_STREAM)
self.theirs = socket.socket(_sock=self.theirsraw)
self.start()
self.ours = ssl.wrap_socket(socket.socket(_sock=self.oursraw), **kwargs)
def run(self):
rl, wl, xl = select.select([self.dest, self.theirs], [], [], 1)
print rl, wl, xl
# FIXME write may block
if self.theirs in rl:
self.dest.send(self.theirs.recv(4096))
if self.dest in rl:
self.theirs.send(self.dest.recv(4096))
def recv(self, *args):
return self.ours.recv(*args)
def send(self, *args):
return self.outs.recv(*args)
def test():
s = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
s.connect(PROXY)
s = ssl.wrap_socket(s, ciphers="ALL:aNULL:eNULL")
s.send(CONNECT)
resp = s.read(4096)
print (resp, )
fs = ForwardedSocket(s, ciphers="ALL:aNULL:eNULL")
fs.send("foobar")
Don't mind custom cihpers=, that only because I didn't want to deal with certificates.
And there's depth-1 ssl output, showing CONNECT, my response to it ssagd and depth-2 ssl negotiation and binary rubbish:
[dima#bmg ~]$ openssl s_server -nocert -cipher "ALL:aNULL:eNULL"
Using default temp DH parameters
Using default temp ECDH parameters
ACCEPT
-----BEGIN SSL SESSION PARAMETERS-----
MHUCAQECAgMDBALAGQQgmn6XfJt8ru+edj6BXljltJf43Sz6AmacYM/dSmrhgl4E
MOztEauhPoixCwS84DL29MD/OxuxuvG5tnkN59ikoqtfrnCKsk8Y9JtUU9zuaDFV
ZaEGAgRSnJ81ogQCAgEspAYEBAEAAAA=
-----END SSL SESSION PARAMETERS-----
Shared ciphers: [snipped]
CIPHER is AECDH-AES256-SHA
Secure Renegotiation IS supported
CONNECT mail.google.com:443 HTTP/1.0
Connection: close
sagq
�u\�0�,�(�$��
�"�!��kj98���� �m:��2�.�*�&���=5�����
��/�+�'�#�� ����g#32��ED���l4�F�1�-�)�%���</�A������
�� ������
�;��A��q�J&O��y�l
It doesn't sound like there's anything wrong with what you're doing; it's certainly possible to call wrap_socket() on an existing SSLSocket.
The 'unknown protocol' error can occur (amongst other reasons) if there's extra data waiting to be read on the socket at the point you call wrap_socket(), for instance an extra \r\n or an HTTP error (due to a missing cert on the server end, for instance). Are you certain you've read everything available at that point?
If you can force the first SSL channel to use a "plain" RSA cipher (i.e. non-Diffie-Hellman) then you may be able to use Wireshark to decrypt the stream to see what's going on.
Building on #kravietz answer. Here is a version that works in Python3 through a Squid proxy:
from OpenSSL import SSL
import socket
def verify_cb(conn, cert, errun, depth, ok):
return True
server = 'mail.google.com'
port = 443
PROXY_ADDR = ("<proxy_server>", 3128)
CONNECT = "CONNECT %s:%s HTTP/1.0\r\nConnection: close\r\n\r\n" % (server, port)
s = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
s.connect(PROXY_ADDR)
s.send(str.encode(CONNECT))
s.recv(4096)
ctx = SSL.Context(SSL.SSLv23_METHOD)
ctx.set_verify(SSL.VERIFY_PEER, verify_cb)
ss = SSL.Connection(ctx, s)
ss.set_connect_state()
ss.do_handshake()
cert = ss.get_peer_certificate()
print(cert.get_subject())
ss.shutdown()
ss.close()
This works in Python 2 also.

Can't send e-mails using python script on digital ocean droplet

I am trying to send e-mails from a production server located on a digital ocean droplet using a office 356 mail server.
The operation executes correctly when I execute the python script on my test server (located on my mac) but fails with code 500 when on the production server.
I am using this code to achieve this:
def __init__(self, from_address="some#mail.com", from_password="somePassword",
smtp_server="smtp.office365.com", smtp_port=587):
self.from_address = from_address
self.from_password = from_password
self.smtp_server = smtp_server
self.smtp_port = smtp_port
def send_mail(self, recipients, subject, message, project_id, pdf_files):
client_id = ProjectClient.query.filter_by(project_id=project_id).first().client_id
client = Client.query.filter_by(client_id=client_id).first()
server = smtplib.SMTP(self.smtp_server, self.smtp_port)
server.ehlo()
server.starttls()
server.ehlo()
server.login(self.from_address, self.from_password)
...
try:
server.sendmail(self.from_address, recipients, message_body.as_string())
I am getting this error:
File "/usr/lib/python3.5/smtplib.py", line 730, in login
raise last_exception
File "/usr/lib/python3.5/smtplib.py", line 721, in login
initial_response_ok=initial_response_ok)
File "/usr/lib/python3.5/smtplib.py", line 627, in auth
initial_response = (authobject() if initial_response_ok else None)
File "/usr/lib/python3.5/smtplib.py", line 664, in auth_login
raise SMTPAuthenticationError(code, resp)
smtplib.SMTPAuthenticationError: (500, b"5.3.3 Unrecognized command 'cmFwcG9ydEBza2ltbWVsZnJpdC5kaw==' [AM5PR0701CA0011.eurprd07.prod.outlook.com]")
Stuff that I tried:
Opened port 587 on the production server
Contacted Office support to add the production server IP adress to the trusted list
This has been fixed by updating python to 3.5.1 (from 3.5.0).

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