Failing to send email with the Python example

Question

I've been trying (and failing) to figure out how to send email via Python.

Trying the example from here: http://docs.python.org/library/smtplib.html#smtplib.SMTP

but added the line server = smtplib.SMTP_SSL('smtp.gmail.com', 465) after I got a bounceback about not having an SSL connection.

Now I'm getting this:

Traceback (most recent call last):
  File "C:/Python26/08_emailconnects/12_29_EmailSendExample_NotWorkingYet.py", line 37, in <module>
    server = smtplib.SMTP('smtp.gmail.com', 65)
  File "C:\Python26\lib\smtplib.py", line 239, in __init__
    (code, msg) = self.connect(host, port)
  File "C:\Python26\lib\smtplib.py", line 295, in connect
    self.sock = self._get_socket(host, port, self.timeout)
  File "C:\Python26\lib\smtplib.py", line 273, in _get_socket
    return socket.create_connection((port, host), timeout)
  File "C:\Python26\lib\socket.py", line 512, in create_connection
    raise error, msg
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
>>> 

Thoughts?

---

server = smtplib.SMTP("smtp.google.com", 495) gives me a timeout error. just smtplib.smtp("smtp.google.com", 495) gives me "SSLError: [Errno 1] _ssl.c:480: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol" (see below).

I'm trying different ports and now I'm getting a completely new error. I'll just post the whole bit of code, I'm probably making some rookie mistake.

"

import smtplib

mailuser = 'MYEMAIL@gmail.com'

mailpasswd = 'MYPASSWORD'

fromaddr = 'MYEMAIL@gmail.com'

toaddrs = 'MYEMAIL2@gmail.com'

msg = 'Hooooorah!'

print msg

server = smtplib.SMTP_SSL('smtp.google.com')

server = smtplib.SMTP_SSL_PORT=587

server.user(mailuser)

server.pass_(mailpasswd)

server.set_debuglevel(1)

server.sendmail(fromaddr, toaddrs, msg)

server.quit()

"

and then I get this error message: "

Traceback (most recent call last):
  File "C:/Python26/08_emailconnects/12_29_eMAILSendtryin_stripped.py", line 16, in <module>
    server = smtplib.SMTP_SSL('smtp.google.com')
  File "C:\Python26\lib\smtplib.py", line 749, in __init__
    SMTP.__init__(self, host, port, local_hostname, timeout)
  File "C:\Python26\lib\smtplib.py", line 239, in __init__
    (code, msg) = self.connect(host, port)
  File "C:\Python26\lib\smtplib.py", line 295, in connect
    self.sock = self._get_socket(host, port, self.timeout)
  File "C:\Python26\lib\smtplib.py", line 755, in _get_socket
    self.sock = ssl.wrap_socket(self.sock, self.keyfile, self.certfile)
  File "C:\Python26\lib\ssl.py", line 350, in wrap_socket
    suppress_ragged_eofs=suppress_ragged_eofs)
  File "C:\Python26\lib\ssl.py", line 118, in __init__
    self.do_handshake()
  File "C:\Python26\lib\ssl.py", line 293, in do_handshake
    self._sslobj.do_handshake()
SSLError: [Errno 1] _ssl.c:480: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol

"

note that actually the which looks like "server = smtplib.SMTPSSLPORT=587" is actually "server = smtplib.SMTP underscore SSL underscore PORT=587", there's some sort of formatting thing going on here.

Answer 1

The following code works for me:

import smtplib

FROMADDR = "my.real.address@gmail.com"
LOGIN    = FROMADDR
PASSWORD = "my.real.password"
TOADDRS  = ["my.real.address@gmail.com"]
SUBJECT  = "Test"

msg = ("From: %s\r\nTo: %s\r\nSubject: %s\r\n\r\n"
       % (FROMADDR, ", ".join(TOADDRS), SUBJECT) )
msg += "some text\r\n"

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()

I'm using Python 2.5.2.

Edit: changed port from 25 to 587 as suggested by ΤΖΩΤΖΙΟΥ, and dropped the second ehlo(). Now I would love to know why port 25 works perfectly from my machine (and port 465 does not).

Answer 2

The correct way to connect to GMail using SSL is:

server = smtplib.SMTP('smtp.gmail.com', 587)

Port 465 seems to cause delays. Both ports are specified in a GMail FAQ.

Note that use of port 587 is more common for SMTP over SSL, although this is just trivial information, it has no other practical use.

This answer is provided as community wiki in order to be chosen as "the" answer. Please improve as needed.

Answer 3

Here's a simple throw away solution. Meant to paste this earlier, but fell asleep at my chair.

import smtplib
import email
import os

username = "user@gmail.com"
passwd = "password"

def mail(to, subject, text, attach):
   msg = MIMEMultipart()

   msg['From'] = username
   msg['To'] = to
   msg['Subject'] = subject

   msg.attach(MIMEText(text)) 

   part = MIMEBase('application', 'octet-stream')
   part.set_payload(open(attach, 'rb').read())
   Encoders.encode_base64(part)
   part.add_header('Content-Disposition',
           'attachment; filename="%s"' % os.path.basename(attach))
   msg.attach(part)

   server = smtplib.SMTP("smtp.gmail.com", 495)
   server.ehlo()
   server.starttls()
   server.ehlo()
   server.login(username, passwd)
   server.sendmail(username, to, msg.as_string())
   server.close()

mail("you", "hi", "hi", "webcam.jpg")

It's my assumption that most people on this thread that have had successful attempts with their code aren't on win32. ;)

*edit: See http://docs.python.org/library/email-examples.html for some good "official" examples.

Answer 4

The problem is due to a bug in Python. Trying to create a connection with SMTP_SSL will fail with "SMTPServerDisconnected: please run connect() first."

A fix has been committed, so you can patch your local copy. See the attachment named "smtplib_72551.diff".

(Note: SMTP_SSL is a new class added to Python 2.6/3.0 and later.)

Answer 5

Okay, found out that this line of code does the trick!

server = smtplib.SMTP('smtp.gmail.com', 587 )

Turned out to be GMAIL didn't support SSL on port 25 (and port 465 caused a hang for some reason).

Thanks guys!

Answer 6

from smtplib import SMTP_SSL as SMTP
from email.mime.text import MIMEText

HOST = 'smtp.gmail.com'
PORT = 465

USERNAME = 'oltjano13@gmail.com'
PASSWORD = ''

SENDER = 'oltjano13@gmail.com'
RECIPIENT = 'oltjano13@gmail.com'

text_subtype = 'plain'

with open('textfile', 'rb') as f:
    msg = MIMEText(f.read(), text_subtype)


msg['Subject'] = 'Python Script'
msg['From'] = SENDER
msg['To'] = RECIPIENT

try:
    connection = SMTP(HOST, PORT)
    connection.login(USERNAME, PASSWORD)
    connection.sendmail(SENDER, RECIPIENT, msg.as_string())
except Exception, e:
    print(e)

The above code works fine for me. As you can see the PORT = 465 is being used in this example since I am using SSL. If you plan to use the port 587 then TLS is required.

Answer 7

Incorrect port maybe? I'm using 587 for smtp.gmail.com and it works.

Answer 8

You should check your port, I'm not sure that google's SMTP port is 65, that would explain the timeout.

Modify your sources as such:

smtplib.SMTP_SSL('smtp.google.com', 465)

If, however, you are certain that it ought to work and it doesn't, it appears that there are some problems with smtplib.SMTP_SSL, and there's an available patch for it here.

Answer 9

import smtplib

content = 'example email stuff here'

mail = smtplib.SMTP('smtp.gmail.com', 587)

mail.ehlo()

mail.starttls()

mail.login('email@gmail.com','password')

mail.sendmail('email@gmail.com', 'email@yahoo.com', content)

mail.close()

Answer 10

Then I had trie to sent email through smtp.gmail.com, I had the same errors. In my case the Internet provider had close the port 25 (and also 587 and other) for outgoing connections from the IP addresses (from my network) to the external network, leaving open the 25th port only for its mail server. So, at first try:

telnet smtp.gmail.com 587

(587 it your port)

By doing this you can understand, if your port is closed by the Internet provider. You can contact your provider and ask them to open a port for you. My solution was connecting to other network (with open port) Here is the code I used:

gmailaddress = "youremailadress@gmail.com"
gmailpassword = "7777777"
mailto = "youremailadress@gmail.com"
msg = input("What is your message? \n ")
mailServer = smtplib.SMTP('smtp.gmail.com' , 587)
mailServer.starttls()
mailServer.login(gmailaddress , gmailpassword)
mailServer.sendmail(gmailaddress, mailto , msg)
print(" \n Sent!")
mailServer.quit()```

Answer 11

After a lot of fiddling with the examples e.g here this now works for me:

import smtplib
from email.mime.text import MIMEText

# SMTP sendmail server mail relay
host = 'mail.server.com'
port = 587 # starttls not SSL 465 e.g gmail,port 25 blocked by most ISPs & AWS
sender_email = 'name@server.com'
recipient_email = 'name@domain.com'
password = 'YourSMTPServerAuthenticationPass'
subject = "Server - "
body = "Message from server"

def sendemail(host, port, sender_email, recipient_email, password, subject, body):
    try:
        p1 = f'<p><HR><BR>{recipient_email}<BR>'
        p2 = f'<h2><font color="green">{subject}</font></h2>'
        p3 = f'<p>{body}'
        p4 = f'<p>Kind Regards,<BR><BR>{sender_email}<BR><HR>'
        
        message = MIMEText((p1+p2+p3+p4), 'html')  
        # servers may not accept non RFC 5321 / RFC 5322 / compliant TXT & HTML typos

        message['From'] = f'Sender Name <{sender_email}>'
        message['To'] = f'Receiver Name <{recipient_email}>'
        message['Cc'] = f'Receiver2 Name <>'
        message['Subject'] = f'{subject}'
        msg = message.as_string()

        server = smtplib.SMTP(host, port)
        print("Connection Status: Connected")
        server.set_debuglevel(1)
        server.ehlo()
        server.starttls()
        server.ehlo()
        server.login(sender_email, password)
        print("Connection Status: Logged in")
        server.sendmail(sender_email, recipient_email, msg)
        print("Status: Email as HTML successfully sent")

    except Exception as e:
            print(e)
            print("Error: unable to send email")

# Run
sendemail(host, port, sender_email, recipient_email, password, subject, body)
print("Status: Exit")