Connect to SMTP (SSL or TLS) using Python - 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)

Related

Sending email(outlook as server) in azure databricks notebook in python?

I tried to configure using localhost. I ran this in my cmd line.
(python -m smtpd -c DebuggingServer -n localhost:1025)
import smtplib, ssl
smtp_server = "localhost"
port = 1025 # For starttls
sender_email = "my outlook email"
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)
print("server connected")
# TODO: Send email here
except Exception as e:
# Print any error messages to stdout
print(e)
finally:
server.quit()
But it is giving "connection refused" error.
To resolve connection refused error, you can try following ways:
Firewall might be blocking access to port 1025
Alternatively, you can try using port 25
As per documentation:
For Enterprise Dev/Test subscriptions, port 25 is blocked by default. It is possible to have this block removed. To request to have the block removed, go to the Cannot send email (SMTP-Port 25) section of the Diagnose and Solve blade in the Azure Virtual Network resource in the Azure portal and run the diagnostic. This will exempt the qualified enterprise dev/test subscriptions automatically.
You can refer to Send emails from Azure Databricks

python imaplib unexpected response 220

I have the following line of code using imaplib
M = imaplib.IMAP4('smtp.gmail.com', 587)
I get the following error from imaplib:
abort: unexpected response: '220 mx.google.com ESMTP o13sm12303588vde.21'
However from reading elsewhere, it seems that that response is the correct response demonstrating that the connection was made to the server successfully at that port.
Why is imaplib giving this error?
You are connecting to the wrong port. 587 is authenticated SMTP, not IMAP; the IMAP designated port number is 143 (or 993 for IMAPS).
I realized I needed to do IMAP4_SSL() - has to be SSL for IMAP and for using IMAP I need the IMAP server for gmail which is imap.googlemail.com. I ultimately got it work without specifying a port. So, final code is:
M = imaplib.IMAP4_SSL('imap.googlemail.com')

How to receive an email over smtpd and sockets

I have some code trying to receive an email sent from a server on a client. The email is definitively sent from the server to the client, and a SMTP server on the client should be able to receive this email. Here is my test implementation:
# define the SMTP server (with the real IP adress of the client of course)
server = smtpd.PureProxy(('XXX.XXX.XXX.XXX', 25), None)
inputs = [server]
outputs = []
message_queues = {}
readable, writable, exceptional = select.select(inputs, outputs, inputs)
# Only one socket in the list returned (there is exactly one)
socket = readable[0]
# Accept the connection or get it or whatever
connection, client_address = socket.accept()
# get the data
data = connection.recv(1024)
print data
After a considerably long time some data is received, which in no way resembles the content of the email. It is always
EHLO YYY.YYY.YYY.YYY
with the YYY the address of the server. I am no expert in SMTP and sockets, but what am I doing wrong to correctly receive the emai and its contents?
Thanks
Alex
The EHLO is part of the SMTP protocol exchange and it represents the client sending its greeting to your server which doesn't respond properly (because it doesn't respond at all). When the client gets tired of waiting for "a considerably long time" the session times out and your server shows what it received.
You seem to be confused as to which process is the server. The smtpd module creates servers or Mail Transport Agents, not clients. As noted in the smtpd documentation for SMTPServer:
Create a new SMTPServer object, which binds to local address
localaddr. It will treat remoteaddr as an upstream SMTP relayer. It
inherits from asyncore.dispatcher, and so will insert itself into
asyncore‘s event loop on instantiation.
You also seem to have the sense of localaddr and remoteaddr confused. The localaddr is not (as your comment claims) the address of the client, but where that server should accept connections from. You might want to try in place of your code:
server = smtpd.DebuggingServer(('localhost', 2525), None)
asyncore.loop()
Which can be tested with client code (in a separate process) of:
client smtplib.SMTP('localhost', 2525)
client.sendmail('from', 'to', 'body')
Finally, having a PureProxy with a remoteaddr of None, it if works at all, would proxy mail into nowhere which is probably not what you want in a proxy.
That is the proper start of the ESMTP protocol dialog. Your program needs to understand and handle at least the basic SMTP verbs; see RFC5321.

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?

xmpp with python: xmpp.protocol.InvalidFrom: (u'invalid-from', '')

cl = xmpp.Client('myserver.com')
if not cl.connect(server=('mysefver.com',5223)):
raise IOError('cannot connect to server')
cl.RegisterHandler('message',messageHandler)
cl.auth('myemail#myserver.com', 'mypassword', 'statusbot')
cl.sendInitPresence()
msgtext = formatToDo(cal, 'text')
message = xmpp.Message('anotheremail#myserver.com', msgtext)
message.setAttr('type', 'chat')
cl.send(message)
I get the following error message when I try to run it:
xmpp.protocol.InvalidFrom: (u'invalid-from', '')
Why is this happening :(
From the XMPP protocol specification:
If the value of the 'from'
address does not match the hostname represented by the Receiving
Server when opening the TCP connection (or any validated domain
thereof, such as a validated subdomain of the Receiving Server's
hostname or another validated domain hosted by the Receiving Server),
then the Authoritative Server MUST generate an stream
error condition and terminate both the XML stream and the underlying
TCP connection.
which basically means, that if the sender is not recognized by the xmpp-server, it'll reply with this message. XMPP supplies a registration mechanism: xmpp.features.register

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