I want to write a program that sends email using Python's smtplib. I searched through the document and the RFCs, but couldn't find anything related to attachments. Thus, I'm sure there's some higher-level concept I'm missing out on. Can someone clue me in on how attachments work in SMTP?
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3Just to be clear, there is nothing at all in SMTP to handle this, it's entirely handled by structuring the document being sent as a MIME document. The article on MIME on wikipedia seems to cover the basic pretty well. – jcoder Dec 27 '09 at 14:45
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3Including a link directly to the "email examples" section of the Python docs would make any answer complete: http://docs.python.org/library/email-examples.html – Peter Hansen Dec 27 '09 at 15:24
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1I believe @PeterHansen's link moved to https://docs.python.org/3/library/email.examples.html – ntc2 Mar 02 '21 at 07:28
6 Answers
Here is an example of a message with a PDF attachment, a text "body" and sending via Gmail.
# Import smtplib for the actual sending function
import smtplib
# For guessing MIME type
import mimetypes
# Import the email modules we'll need
import email
import email.mime.application
# Create a text/plain message
msg = email.mime.Multipart.MIMEMultipart()
msg['Subject'] = 'Greetings'
msg['From'] = 'xyz@gmail.com'
msg['To'] = 'abc@gmail.com'
# The main body is just another attachment
body = email.mime.Text.MIMEText("""Hello, how are you? I am fine.
This is a rather nice letter, don't you think?""")
msg.attach(body)
# PDF attachment
filename='simple-table.pdf'
fp=open(filename,'rb')
att = email.mime.application.MIMEApplication(fp.read(),_subtype="pdf")
fp.close()
att.add_header('Content-Disposition','attachment',filename=filename)
msg.attach(att)
# send via Gmail server
# NOTE: my ISP, Centurylink, seems to be automatically rewriting
# port 25 packets to be port 587 and it is trashing port 587 packets.
# So, I use the default port 25, but I authenticate.
s = smtplib.SMTP('smtp.gmail.com')
s.starttls()
s.login('xyz@gmail.com','xyzpassword')
s.sendmail('xyz@gmail.com',['xyz@gmail.com'], msg.as_string())
s.quit()

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2This solved my problem for emailing excel files as well which was awesome because it kept me out of os.system calling Ruby! Thanks Kevin! – Benjooster Aug 16 '13 at 18:38
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This solution also worked for me, after creating a .xls file using the Python xlwt module. Instead of sending over Gmail I used my company's mail server. Thanks, and +1 – nicholsonjf Dec 27 '13 at 19:34
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adding the header (in python2.7.9) didn't name the file properly. My fix was to change the line to: `att.add_header('Content-Disposition', 'attachment; filename=%s' % filename)` – wprins Dec 21 '15 at 17:14
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Greetings from 2017! I'm running this code (with one modification: `smtplib.SMTP('smtp.gmail.com', 587)` ) and it seems that whenever I run it my connection speed drops to 1996 levels. It's really strange. Any advice? TIA – Optimesh Oct 13 '17 at 18:45
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@Optimesh - in my opinion, there can be no connection between running this and your connection speed. Maybe you have antivirus sniffing your outgoing emails. – Kevin Buchs Oct 18 '17 at 11:50
Here's an example I snipped out of a work application we did. It creates an HTML email with an Excel attachment.
import smtplib,email,email.encoders,email.mime.text,email.mime.base
smtpserver = 'localhost'
to = ['email@somewhere.com']
fromAddr = 'automated@hi.com'
subject = "my subject"
# create html email
html = '<!DOCTYPE html PUBLIC "-//W3C//DTD XHTML 1.0 Transitional//EN" '
html +='"http://www.w3.org/TR/xhtml1/DTD/xhtml1-transitional.dtd"><html xmlns="http://www.w3.org/1999/xhtml">'
html +='<body style="font-size:12px;font-family:Verdana"><p>...</p>'
html += "</body></html>"
emailMsg = email.MIMEMultipart.MIMEMultipart('alternative')
emailMsg['Subject'] = subject
emailMsg['From'] = fromAddr
emailMsg['To'] = ', '.join(to)
emailMsg['Cc'] = ", ".join(cc)
emailMsg.attach(email.mime.text.MIMEText(html,'html'))
# now attach the file
fileMsg = email.mime.base.MIMEBase('application','vnd.ms-excel')
fileMsg.set_payload(file('exelFile.xls').read())
email.encoders.encode_base64(fileMsg)
fileMsg.add_header('Content-Disposition','attachment;filename=anExcelFile.xls')
emailMsg.attach(fileMsg)
# send email
server = smtplib.SMTP(smtpserver)
server.sendmail(fromAddr,to,emailMsg.as_string())
server.quit()

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6The multipart subtype should be 'mixed' instead of 'alternative' otherwise you won't see the attached file in some email clients. – rhyek Apr 07 '12 at 15:05
What you want to check out is the email
module. It lets you build MIME-compliant messages that you then send with smtplib.

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Well, attachments are not treated in any special ways, they are "just" leaves of the Message-object tree. You can find the answers to any questions regarding MIME-compliant mesasges in this section of the documentation on the email python package.
In general, any kind of attachment (read: raw binary data) can be represented by using base64
(or similar) Content-Transfer-Encoding
.

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Here's how to send e-mails with zip file attachments and utf-8 encoded subject+body.
It was not straightforward to figure this one out, due to lack of documentation and samples for this particular case.
Non-ascii characters in replyto needs to be encoded with, for instance, ISO-8859-1. There probably exists a function that can do this.
Tip:
Send yourself an e-mail, save it and examine the content to figure out how to do the same thing in Python.
Here's the code, for Python 3:
#!/usr/bin/env python3
# -*- coding: utf-8 -*-
# vim:set ts=4 sw=4 et:
from os.path import basename
from smtplib import SMTP
from email.mime.text import MIMEText
from email.mime.base import MIMEBase
from email.mime.multipart import MIMEMultipart
from email.header import Header
from email.utils import parseaddr, formataddr
from base64 import encodebytes
def send_email(recipients=["somebody@somewhere.xyz"],
subject="Test subject æøå",
body="Test body æøå",
zipfiles=[],
server="smtp.somewhere.xyz",
username="bob",
password="password123",
sender="Bob <bob@somewhere.xyz>",
replyto="=?ISO-8859-1?Q?M=F8=F8=F8?= <bob@somewhere.xyz>"): #: bool
"""Sends an e-mail"""
to = ",".join(recipients)
charset = "utf-8"
# Testing if body can be encoded with the charset
try:
body.encode(charset)
except UnicodeEncodeError:
print("Could not encode " + body + " as " + charset + ".")
return False
# Split real name (which is optional) and email address parts
sender_name, sender_addr = parseaddr(sender)
replyto_name, replyto_addr = parseaddr(replyto)
sender_name = str(Header(sender_name, charset))
replyto_name = str(Header(replyto_name, charset))
# Create the message ('plain' stands for Content-Type: text/plain)
try:
msgtext = MIMEText(body.encode(charset), 'plain', charset)
except TypeError:
print("MIMEText fail")
return False
msg = MIMEMultipart()
msg['From'] = formataddr((sender_name, sender_addr))
msg['To'] = to #formataddr((recipient_name, recipient_addr))
msg['Reply-to'] = formataddr((replyto_name, replyto_addr))
msg['Subject'] = Header(subject, charset)
msg.attach(msgtext)
for zipfile in zipfiles:
part = MIMEBase('application', "zip")
b = open(zipfile, "rb").read()
# Convert from bytes to a base64-encoded ascii string
bs = encodebytes(b).decode()
# Add the ascii-string to the payload
part.set_payload(bs)
# Tell the e-mail client that we're using base 64
part.add_header('Content-Transfer-Encoding', 'base64')
part.add_header('Content-Disposition', 'attachment; filename="%s"' %
os.path.basename(zipfile))
msg.attach(part)
s = SMTP()
try:
s.connect(server)
except:
print("Could not connect to smtp server: " + server)
return False
if username:
s.login(username, password)
print("Sending the e-mail")
s.sendmail(sender, recipients, msg.as_string())
s.quit()
return True
def main():
send_email()
if __name__ == "__main__":
main()

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# -*- coding: utf-8 -*-
"""
Mail sender
"""
from email.mime.multipart import MIMEMultipart
from email.mime.text import MIMEText
import smtplib
import pystache
import codecs
import time
import sys
reload(sys)
sys.setdefaultencoding('utf-8')
HOST = 'smtp.exmail.qq.com'
PORT = 587
USER = 'your@mail.com'
PASS = 'yourpass'
FROM = 'your@mail.com'
SUBJECT = 'subject'
HTML_NAME = 'tpl.html'
CSV_NAME = 'list.txt'
FAILED_LIST = []
def send(mail_receiver, mail_to):
# text = mail_text
html = render(mail_receiver)
# msg = MIMEMultipart('alternative')
msg = MIMEMultipart('mixed')
msg['From'] = FROM
msg['To'] = mail_to.encode()
msg['Subject'] = SUBJECT.encode()
# msg.attach(MIMEText(text, 'plain', 'utf-8'))
msg.attach(MIMEText(html, 'html', 'utf-8'))
try:
_sender = smtplib.SMTP(
HOST,
PORT
)
_sender.starttls()
_sender.login(USER, PASS)
_sender.sendmail(FROM, mail_to, msg.as_string())
_sender.quit()
print "Success"
except smtplib.SMTPException, e:
print e
FAILED_LIST.append(mail_receiver + ',' + mail_to)
def render(name):
_tpl = codecs.open(
'./html/' + HTML_NAME,
'r',
'utf-8'
)
_html_string = _tpl.read()
return pystache.render(_html_string, {
'receiver': name
})
def main():
ls = open('./csv/' + CSV_NAME, 'r')
mail_list = ls.read().split('\r')
for _receiver in mail_list:
_tmp = _receiver.split(',')
print 'Mail: ' + _tmp[0] + ',' + _tmp[1]
time.sleep(20)
send(_tmp[0], _tmp[1])
print FAILED_LIST
main()

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