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')

Solution 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.

Solution 2

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('[email protected]')
yag.send('[email protected]', subject = None, contents = 'Hello')

Or a one liner:

yagmail.SMTP('[email protected]').send('[email protected]', 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("[email protected]", "mypassword")

and exit. Then you can just use:

import yagmail
yagmail.SMTP("[email protected]") # without password

If you add .yagmail with "[email protected]" 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("[email protected]", 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.

Solution 3

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'] = "..."

Solution 4

I don't know if OP still cares about this answer, but having found myself here in an effort to troubleshoot a similar problem, hopefully someone else might find this useful. As it turns out, Google has changed the way that they allow their SMTP server to be used. You will want to check a couple of things:

1. That you are using the same address you used to authenticate as the 'from' address. If I am not mistaken it used to be the case that you could put pretty much whatever you wanted in the from field, but for security purposes many SMTP host sites (including google) now restrict this to the address that has authenticated with them.

2. Allow your account to be accessed by 'less secure apps' (read: apps we do not generate revenue from). To do that log into your account and navigate here: https://www.google.com/settings/security/lesssecureapps

3. Use port 587 with tls. Not really sure why but I could never get port 465 to play nice.

Hope this helps somebody else out.

Solution 5

save yourselves some headaches and use this:

http://mynthon.net/howto/-/python/python%20-%20logging.SMTPHandler-how-to-use-gmail-smtp-server.txt

Python SMTPHandler with GMail

Ss

View more solutions

Comments

[rohanlatimer]

You can send the mail via your normal SMTP relay, instead of calling gmail directly.

[trusktr]

How do you turn on debug mode to get those output messages?

[hd1]

smtplib.set_debuglevel(True) will sort you, @trusktr

[Charlie Parker]

I don't understand, how does the accepted answer solve your problem? What piece of code do I copy paste so that I can send an e-mail?

[hwiechers]

I think it's the ISP. I tried the code and it worked fine for me.

[Piotr Findeisen]

If GMail did reverse DNS lookup and refused connections, then how could i use my desktop email client, like thunderbird, to send mails via gmail's smtp?

[PascalVKooten]

Thanks for the upvote, I'm really trying to get more attention to the package!

[Amit Tripathi]

SMTPAuthenticationError: Please log in via your web browser and\n5.7.14 then try again.\n5.7.14 Learn more at\n5.7.14 https://support.google.com/mail/answer/78754 vl1sm48001045pbc.31 - gsmtp')

[PascalVKooten]

@Death-Stalker Seems like you made a mistake with writing your password?

[Amit Tripathi]

no. I tested it like 4-5 times and I am sure my password is right.

[O. Edholm]

Answer, where have you been?!

[Charlie Parker]

I'm confused, where are there a clear set of instructions for how to send an e-mail within python?

[Charlie Parker]

not that I am against your library or anything but why is it so difficult to send an e-mail in python?

[Charlie Parker]

can you explain in more details how to actually make it work? especially the part "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."

[PascalVKooten]

@CharlieParker it's optional though. You can also just have it in your script if you are too lazy to read the documentation. Or you can set up OAuth2. It's all in the docs: yagmail.readthedocs.io

[PascalVKooten]

I guess this was one of my earlier posts on stackoverflow. I'll add specifically the keyring part in the answer.

[krayzk]

@CharlieParker the instructions can be found in the original question, my answer was to point out possible reasons that what OP was doing wasn't working.

[sh37211]

@PascalVKooten Looks neat. Unfortunately running yagmail.register line produces NameError: name 'keyring' is not defined. I see your post is 6 years old so probably something changed.

[PascalVKooten]

@sh37211 I would recommend to set up an application specific password in gmail and just use that