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 = '[email protected]'

mailpasswd = 'MYPASSWORD'

fromaddr = '[email protected]'

toaddrs = '[email protected]'

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 = "[email protected]"
LOGIN    = FROMADDR
PASSWORD = "my.real.password"
TOADDRS  = ["[email protected]"]
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

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.)