send email via hotmail in python

Question

I want to send an email from my server. I'm trying to send using a hotmail account that I already have.

user = "[e-mail]"
passwd = "xxxxxxxxx"

from_addr = "[e-mail]"
to_addr = "[e-mail]"
smtp_srv = "smtp.live.com"

subject = "Home Server Uptime"
message = "The server has been online for: %s" %(uptime)

smtp = smtplib.SMTP(smtp_srv,587)
smtp.ehlo()
smtp.starttls()
smtp.ehlo()
smtp.login(user, passwd)
smtp.sendmail(from_addr, to_addr, message)
smtp.quit()

I get this error:

Traceback (most recent call last):
  File "sendemail.py", line 23, in <module>
    smtp.starttls()
  File "/usr/lib/python2.7/smtplib.py", line 636, in starttls
    (resp, reply) = self.docmd("STARTTLS")
  File "/usr/lib/python2.7/smtplib.py", line 385, in docmd
    return self.getreply()
  File "/usr/lib/python2.7/smtplib.py", line 358, in getreply
    + str(e))
smtplib.SMTPServerDisconnected: Connection unexpectedly closed: [Errno 104] Connection reset by peer

I have no idea how to troubleshoot this.

Here is the output of set_debuglevel(1) as Nathan suggested:

send: 'ehlo [127.0.1.1]\r\n'
reply: '250-BLU0-SMTP190.blu0.hotmail.com Hello [my-ip-address]\r\n'
reply: '250-TURN\r\n'
reply: '250-SIZE 41943040\r\n'
reply: '250-ETRN\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-DSN\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250-8bitmime\r\n'
reply: '250-BINARYMIME\r\n'
reply: '250-CHUNKING\r\n'
reply: '250-VRFY\r\n'
reply: '250-TLS\r\n'
reply: '250-STARTTLS\r\n'
reply: '250 OK\r\n'
reply: retcode (250); Msg: BLU0-SMTP190.blu0.hotmail.com Hello [my-ip-address]
TURN
SIZE 41943040
ETRN
PIPELINING
DSN
ENHANCEDSTATUSCODES
8bitmime
BINARYMIME
CHUNKING
VRFY
TLS
STARTTLS
OK
send: 'STARTTLS\r\n'
Traceback (most recent call last):
  File "sendemail.py", line 24, in <module>
    smtp.starttls()
  File "/usr/lib/python2.7/smtplib.py", line 636, in starttls
    (resp, reply) = self.docmd("STARTTLS")
  File "/usr/lib/python2.7/smtplib.py", line 385, in docmd
    return self.getreply()
  File "/usr/lib/python2.7/smtplib.py", line 358, in getreply
    + str(e))
smtplib.SMTPServerDisconnected: Connection unexpectedly closed: [Errno 104] Connection reset by peer

Answer 1

It looks like your code is failing when trying to start TLS (smtp.starttls()). I just tested smtp.live.com and I was able to get to the line in your code where you attempt to login, so it might be something due to how your network is setup.

This is unrelated, but according to the smtplib docs, you have to add the from and to address headers at the beginning of the message:

parts = ("From: " + from_addr,
         "To: " + to_addr,
         "Subject: " + subject,
         "",
         message)    
msg = '\r\n'.join(parts)

Answer 2

try this

import email
import smtplib

msg = email.message_from_string('warning')
msg['From'] = "[e-mail]"
msg['To'] = "[e-mail]"
msg['Subject'] = "helOoooOo"

s = smtplib.SMTP("smtp.live.com",587)
s.ehlo() # Hostname to send for this command defaults to the fully qualified domain name of the local host.
s.starttls() #Puts connection to SMTP server in TLS mode
s.ehlo()
s.login('[e-mail]', 'pass')

s.sendmail("[e-mail]", "[e-mail]", msg.as_string())

s.quit()