smtplib and gmail - python script problems

Question

Here's my script:

#!/usr/bin/python

import smtplib
msg = 'Hello world.'

server = smtplib.SMTP('smtp.gmail.com',587) #port 465 or 587
server.ehlo()
server.starttls()
server.ehlo()
server.login('[email protected]','mypass')
server.sendmail('[email protected]','[email protected]',msg)
server.close()

I'm just trying to send an email from my gmail account. The script uses starttls because of gmail's requirement. I've tried this on two web hosts, 1and1 and webfaction. 1and1 gives me a 'connection refused' error and webfaction reports no error but just doesn't send the email. I can't see anything wrong with the script, so I'm thinking it might be related to the web hosts. Any thoughts and comments would be much appreciated.

EDIT: I turned on debug mode. From the output, it looks like it sent the message successfully...I just never receive it.

send: 'ehlo web65.webfaction.com\r\n'
reply: '250-mx.google.com at your service, [174.133.21.84]\r\n'
reply: '250-SIZE 35651584\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-STARTTLS\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250 PIPELINING\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [174.133.21.84]
SIZE 35651584
8BITMIME
STARTTLS
ENHANCEDSTATUSCODES
PIPELINING
send: 'STARTTLS\r\n'
reply: '220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: 2.0.0 Ready to start TLS
send: 'ehlo web65.webfaction.com\r\n'
reply: '250-mx.google.com at your service, [174.133.21.84]\r\n'
reply: '250-SIZE 35651584\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250 PIPELINING\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [174.133.21.84]
SIZE 35651584
8BITMIME
AUTH LOGIN PLAIN
ENHANCEDSTATUSCODES
PIPELINING
send: 'AUTH PLAIN *****\r\n'
reply: '235 2.7.0 Accepted\r\n'
reply: retcode (235); Msg: 2.7.0 Accepted
send: 'mail FROM:<[email protected]> size=12\r\n'
reply: '250 2.1.0 OK 4sm652580yxq.48\r\n'
reply: retcode (250); Msg: 2.1.0 OK 4sm652580yxq.48
send: 'rcpt TO:<[email protected]>\r\n'
reply: '250 2.1.5 OK 4sm652580yxq.48\r\n'
reply: retcode (250); Msg: 2.1.5 OK 4sm652580yxq.48
send: 'data\r\n'
reply: '354  Go ahead 4sm652580yxq.48\r\n'
reply: retcode (354); Msg: Go ahead 4sm652580yxq.48
data: (354, 'Go ahead 4sm652580yxq.48')
send: 'Hello world.\r\n.\r\n'
reply: '250 2.0.0 OK 1240421143 4sm652580yxq.48\r\n'
reply: retcode (250); Msg: 2.0.0 OK 1240421143 4sm652580yxq.48
data: (250, '2.0.0 OK 1240421143 4sm652580yxq.48')

Answer 1

I think that the GMail SMTP server does a reverse DNS lookup on the IP address that you connect from, and refuses the connection if no domain can be found. This is to avoid spammer from using their SMTP server as an open relay.

Answer 2

Have you tried constructing a valid message?

from email.MIMEText import MIMEText

msg = MIMEText('body')
msg['Subject'] = 'subject'
msg['From'] = "..."
msg['Reply-to'] = "..."
msg['To'] = "..."

Answer 3

You'll need to check your "Sent" folder in GMail, as that's where a message sent from your account to your account will most probably show up.