This is an old question. My main reason to post a new answer is to explain how to solve the problem with the modern email
library in Python 3.6+ and how it differs from the old version; but first, let's recap what Anony-Mousse wrote in their answer from 2012.
SMTP doesn't care at all what's in the headers. The list of recipients you pass in to the sendmail
method are what actually determine where the message will be delivered.
In SMTP parlance, this is called the message's envelope. On the protocol level, you connect to the server, then tell it who the message is from (MAIL FROM:
SMTP verb) and who to send it to (RCPT TO:
), then separately transmit the message itself (DATA
) with headers and body as one oblique string blob.
The modern smtplib
simplifies the Python side of this by providing a send_message
method which actually sends to the recipients specified in the message's headers.
The modern email
library provides an EmailMessage
object which replaces all the various individual MIME types which you had to use in the past to assemble a message from smaller parts. You can add attachments without separately constructing them, and build various more complex multipart structures if you need to, but you normally don't have to. Just create a message and populate the parts you want.
Notice that the following is heavily commented; on the whole, the new EmailMessage
API is more succinct and more versatile than the old API.
from email.message import EmailMessage
msg = EmailMessage()
# This example uses explicit strings to emphasize that
# that's what these header eventually get turned into
msg["From"] = "me@example.org"
msg["To"] = "main.recipient@example.net, other.main.recipient@example.org"
msg["Cc"] = "secondary@example.com, tertiary@example.eu"
msg["Bcc"] = "invisible@example.int, undisclosed@example.org.au"
msg["Subject"] = "Hello from the other side"
msg.set_content("This is the main text/plain message.")
# You can put an HTML body instead by adding a subtype string argument "html"
# msg.set_content("<p>This is the main text/html message.</p>", "html")
# You can add attachments of various types as you see fit;
# if there are no other parts, the message will be a simple
# text/plain or text/html, but Python will change it into a
# suitable multipart/related or etc if you add more parts
with open("image.png", "rb") as picture:
msg.add_attachment(picture.read(), maintype="image", subtype="png")
# Which port to use etc depends on the mail server.
# Traditionally, port 25 is SMTP, but modern SMTP MSA submission uses 587.
# Some servers accept encrypted SMTP_SSL on port 465.
# Here, we use SMTP instead of SMTP_SSL, but pivot to encrypted
# traffic with STARTTLS after the initial handshake.
with smtplib.SMTP("smtp.example.org", 587) as server:
# Some servers insist on this, others are more lenient ...
# It is technically required by ESMTP, so let's do it
# (If you use server.login() Python will perform an EHLO first
# if you haven't done that already, but let's cover all bases)
server.ehlo()
# Whether or not to use STARTTLS depends on the mail server
server.starttls()
# Bewilderingly, some servers require a second EHLO after STARTTLS!
server.ehlo()
# Login is the norm rather than the exception these days
# but if you are connecting to a local mail server which is
# not on the public internet, this might not be useful or even possible
server.login("me.myself@example.org", "xyzzy")
# Finally, send the message
server.send_message(msg)
The ultimate visibility of the Bcc:
header depends on the mail server. If you want to be really sure that the recipients are not visible to each other, perhaps don't put a Bcc:
header at all, and separately enumerate the envelope recipients in the envelope like you used to have to with sendmail
(send_message
lets you do that too, but you don't have to if you just want to send to the recipients named in the headers).
This obviously sends a single message to all recipients in one go. That is generally what you should be doing if you are sending the same message to a lot of people. However, if each message is unique, you will need to loop over the recipients and create and send a new message for each. (Merely wishing to put the recipient's name and address in the To:
header is probably not enough to warrant sending many more messages than required, but of course, sometimes you have unique content for each recipient in the body, too.)