How can I connect to a mail server using SMTP over SSL using Python?

Question

So I have been having a hard time sending email from my school's email address. It is SSL and I could only find this code online by Matt Butcher that works with SSL:

import smtplib, socket

__version__ = "1.00"

__all__ = ['SMTPSSLException', 'SMTP_SSL']

SSMTP_PORT = 465

class SMTPSSLException(smtplib.SMTPException):
    """Base class for exceptions resulting from SSL negotiation."""

class SMTP_SSL (smtplib.SMTP):
    """This class provides SSL access to an SMTP server.
    SMTP over SSL typical listens on port 465. Unlike StartTLS, SMTP over SSL
    makes an SSL connection before doing a helo/ehlo. All transactions, then,
    are done over an encrypted channel.

    This class is a simple subclass of the smtplib.SMTP class that comes with
    Python. It overrides the connect() method to use an SSL socket, and it
    overrides the starttles() function to throw an error (you can't do 
    starttls within an SSL session).
    """
    certfile = None
    keyfile = None

    def __init__(self, host='', port=0, local_hostname=None, keyfile=None, certfile=None):
        """Initialize a new SSL SMTP object.

        If specified, `host' is the name of the remote host to which this object
        will connect. If specified, `port' specifies the port (on `host') to
        which this object will connect. `local_hostname' is the name of the
        localhost. By default, the value of socket.getfqdn() is used.

        An SMTPConnectError is raised if the SMTP host does not respond 
        correctly.

        An SMTPSSLError is raised if SSL negotiation fails.

        Warning: This object uses socket.ssl(), which does not do client-side
        verification of the server's cert.
        """
        self.certfile = certfile
        self.keyfile = keyfile
        smtplib.SMTP.__init__(self, host, port, local_hostname)

    def connect(self, host='localhost', port=0):
        """Connect to an SMTP server using SSL.

        `host' is localhost by default. Port will be set to 465 (the default
        SSL SMTP port) if no port is specified.

        If the host name ends with a colon (`:') followed by a number, 
        that suffix will be stripped off and the
        number interpreted as the port number to use. This will override the 
        `port' parameter.

        Note: This method is automatically invoked by __init__, if a host is
        specified during instantiation.
        """
        # MB: Most of this (Except for the socket connection code) is from 
        # the SMTP.connect() method. I changed only the bare minimum for the 
        # sake of compatibility.
        if not port and (host.find(':') == host.rfind(':')):
            i = host.rfind(':')
            if i >= 0:
                host, port = host[:i], host[i+1:]
                try: port = int(port)
                except ValueError:
                    raise socket.error, "nonnumeric port"
        if not port: port = SSMTP_PORT
        if self.debuglevel > 0: print>>stderr, 'connect:', (host, port)
        msg = "getaddrinfo returns an empty list"
        self.sock = None
        for res in socket.getaddrinfo(host, port, 0, socket.SOCK_STREAM):
            af, socktype, proto, canonname, sa = res
            try:
                self.sock = socket.socket(af, socktype, proto)
                if self.debuglevel > 0: print>>stderr, 'connect:', (host, port)
                self.sock.connect(sa)
                # MB: Make the SSL connection.
                sslobj = socket.ssl(self.sock, self.keyfile, self.certfile)
            except socket.error, msg:
                if self.debuglevel > 0: 
                    print>>stderr, 'connect fail:', (host, port)
                if self.sock:
                    self.sock.close()
                self.sock = None
                continue
            break
        if not self.sock:
            raise socket.error, msg

        # MB: Now set up fake socket and fake file classes.
        # Thanks to the design of smtplib, this is all we need to do
        # to get SSL working with all other methods.
        self.sock = smtplib.SSLFakeSocket(self.sock, sslobj)
        self.file = smtplib.SSLFakeFile(sslobj);

        (code, msg) = self.getreply()
        if self.debuglevel > 0: print>>stderr, "connect:", msg
        return (code, msg)

    def setkeyfile(self, keyfile):
        """Set the absolute path to a file containing a private key.

        This method will only be effective if it is called before connect().

        This key will be used to make the SSL connection."""
        self.keyfile = keyfile

    def setcertfile(self, certfile):
        """Set the absolute path to a file containing a x.509 certificate.

        This method will only be effective if it is called before connect().

        This certificate will be used to make the SSL connection."""
        self.certfile = certfile

    def starttls():
        """Raises an exception. 
        You cannot do StartTLS inside of an ssl session. Calling starttls() will
        return an SMTPSSLException"""
        raise SMTPSSLException, "Cannot perform StartTLS within SSL session."

And then my code:

import ssmtplib
conn = ssmtplib.SMTP_SSL('HOST')
conn.login('USERNAME','PW')
conn.ehlo()
conn.sendmail('FROM_EMAIL', 'TO_EMAIL', "MESSAGE")
conn.close()

And got this error:

/Users/Jake/Desktop/Beth's Program/ssmtplib.py:116: DeprecationWarning: socket.ssl() is deprecated.  Use ssl.wrap_socket() instead.
  sslobj = socket.ssl(self.sock, self.keyfile, self.certfile)
Traceback (most recent call last):
  File "emailer.py", line 5, in 
    conn = ssmtplib.SMTP_SSL('HOST')
  File "/Users/Jake/Desktop/Beth's Program/ssmtplib.py", line 79, in init
    smtplib.SMTP.init(self, host, port, local_hostname)
  File "/Library/Frameworks/Python.framework/Versions/2.6/lib/python2.6/smtplib.py", line 239, in init
    (code, msg) = self.connect(host, port)
  File "/Users/Jake/Desktop/Beth's Program/ssmtplib.py", line 131, in connect
    self.sock = smtplib.SSLFakeSocket(self.sock, sslobj)
AttributeError: 'module' object has no attribute 'SSLFakeSocket'

Thank you!

Answer 1

That code you've found seems to be for an older version, considering the deprecation warning. Maybe you can get by with the stdlib: There is a SMTP_SSL class as of Python 2.6, and as of at least 2.4 there is a starttls method on the plaintext SMTP class.