530-5.5.1 Authentication Required

from socket import *
import ssl, pprint

msg = "rn I love computer networks!"
endmsg = "rn.rn"

# Choose a mail server (e.g. Google mail server) and call it mailserver
mailserver = "smtp.gmail.com"
port = 465

# Create socket called clientSocket and establish a TCP connection with mailserver
clientSocket = socket(AF_INET, SOCK_STREAM)
ssl_clientSocket = ssl.wrap_socket(clientSocket)
                                   #ca_certs="C:UserswgimsonDownloadsroot",
                                   #cert_reqs=ssl.CERT_REQUIRED)
ssl_clientSocket.connect((mailserver, port))

# DEBUG
print repr(ssl_clientSocket.getpeername())
print ssl_clientSocket.cipher()
print pprint.pformat(ssl_clientSocket.getpeercert())
# DEBUG


recv = ssl_clientSocket.read(1024)
print
print recv


# If the first three numbers of what we receive from the SMTP server are not
# '220', we have a problem
if recv[:3] != '220':
    print '220 reply not received from server.'
else:
    print "220 is good"

# Send HELO command and print server response.
heloCommand = 'HELO Alicern'
ssl_clientSocket.write(heloCommand)
recv1 = ssl_clientSocket.recv(1024)
print recv1


# If the first three numbers of the response from the server are not
# '250', we have a problem
if recv1[:3] != '250':
    print '250 reply not received from server.'
else:
    print "250 is good"


# Send MAIL FROM command and print server response.
mailFromCommand = 'MAIL From: wgimson@gmail.comrn'
ssl_clientSocket.send(mailFromCommand)
recv2 = ssl_clientSocket.recv(1024)
print recv2

# If the first three numbers of the response from the server are not
# '250', we have a problem
if recv2[:3] != '250':
    print '250 reply not received from server.'
else:
    print "250 means still good"

def send_mail(recipient, subject, message, contenttype='plain'):
    EMAIL_HOST = 'smtp.gmail.com'
    EMAIL_PORT = 587
    EMAIL_HOST_USER = 'some_account@gmail.com'
    EMAIL_HOST_PASSWORD = 'some_password'

    mime_msg = email.mime.text.MIMEText(message, contenttype, _charset="UTF-8")
    mime_msg['Subject'] = subject
    mime_msg['From'] = EMAIL_HOST_USER
    mime_msg['To'] = recipient

    smtpserver = smtplib.SMTP(EMAIL_HOST, EMAIL_PORT)
    smtpserver.ehlo()
    smtpserver.starttls()
    smtpserver.login(EMAIL_HOST_USER, EMAIL_HOST_PASSWORD)
    smtpserver.sendmail(EMAIL_HOST_USER, recipient, mime_msg.as_string())
    smtpserver.close()