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

Answer 1

Some self-promotion here, but I feel on a valid ground.

You would literally only need this code to do exactly what you wrote:

import yagmail
yag = yagmail.SMTP('myname@gmail.com')
yag.send('somename@somewhere.com', subject = None, contents = 'Hello')

Or a one liner:

yagmail.SMTP('myname@gmail.com').send('somename@somewhere.com', None, 'Hello world.')

What is nice is that I propose to use keyring to store your password, so you never have a risk of people seeing your password in your script.

You can set this up by running once in your interpreter:

import yagmail
yagmail.register("my@gmail.com", "mypassword")

and exit. Then you can just use:

import yagmail
yagmail.SMTP("my@gmail.com") # without password

If you add .yagmail with "my@gmail.com" in your home dir, then you can just do: yagmail.SMTP(), but that's rather pointless by now.

Warning: If you get serious about sending a lot of messages, better set up OAuth2, yagmail can help with that.

yagmail.SMTP("my@gmail.com", oauth2_file="/path/to/save/creds.json")

The first time ran, it will guide you through the process of getting OAuth2 credentials and store them in the file so that next time you don't need to do anything with it. Do you suspect someone found your credentials? They'll have limited permissions, but you better invalidate their credentials through gmail.

For the package/installation please look at git or readthedocs, available for both Python 2 and 3.