On Sun, Nov 18, 2012 at 12:23 AM, Saad Javed <sbja...@gmail.com> wrote:

> import smtplib
>
> from_addr = "some_a...@hotmail.com"
> to_addr = "some_a...@gmail.com"
> smtp_srv = "smtp.live.com"
>
> subject = "Test"
> message = "Test"
>
> msg = "To:%s\nFrom:%s\nSubject: %s\n\n%s" % (to_addr, from_addr, subject,
> message)
>
> smtp = smtplib.SMTP(smtp_srv, 587)
> smtp.set_debuglevel(1)
> smtp.ehlo()
> smtp.starttls()
> smtp.ehlo()
> smtp.login(user, passwd)
> smtp.sendmail(from_addr, to_addr, msg)
> smtp.quit()
>
> When I run this code, I get this output:
> 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
>
> I can send email via browser. Why is my authentication being blocked by
> hotmail?
>
> P.S: I tried sending from gmail. Same error.
>
> Saad
>
> You start TLS but is the connection to the server secured using SSL?
Usually email providers have particular ports and types of encryption that
must be specified to authenticate before you can DL an entire inbox or send
a message from the address.
Alexander
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