sendmails.py

#!/usr/bin/env python
# Send an HTML email to all addresses in a txt file

import argparse, sys, smtplib, datetime, re, os, random, base64, time, html2text
from email import Encoders
from email.MIMEBase import MIMEBase
from email.mime.application import MIMEApplication
from email.mime.multipart import MIMEMultipart
from email.mime.text import MIMEText 
from email.mime.image import MIMEImage
from email.header import Header

parser = argparse.ArgumentParser(description="Wrapper for NTLM info leak and NTLM dictionary attack")
parser.add_argument("-e", "--emails", help="File containing list of email addresses")
parser.add_argument("-E", "--email", help="Single email address to send to")
parser.add_argument("-b", "--body", help="File containing HTML body of email")
parser.add_argument("-t", "--text", action="store_true", help="Add a plain text part to the email converted from the HTML body (use if the target mail client doesn't display HTML inline, e.g. IBM Notes might not)")
parser.add_argument("-s", "--subject", help="Subject line of email")
parser.add_argument("-f", "--fromheader", help="From address (address or 'name <address>')")
parser.add_argument("-r", "--readreceipt", help="Read receipt address (same format as from/to headers")
parser.add_argument("-g", "--host", help="SMTP host")
parser.add_argument("-P", "--port", help="SMTP port")
parser.add_argument("-u", "--username", help="SMTP username")
parser.add_argument("-p", "--password", help="SMTP password")
parser.add_argument("-d", "--delay", help="Delay between mail sends (seconds)")
parser.add_argument("-a", "--attachment", help="Filename to add as an attachment")
args = parser.parse_args()

if not args.body or not args.subject or not args.fromheader:
  parser.print_usage()
  sys.exit(2)

if not args.emails and not args.email:
  parser.print_usage()
  sys.exit(2)

# if args.host and ( not args.username and not args.password ):
#   print 'Username and password required when specifying host'
#   sys.exit(2)
#   if not args.port:
#     args.port = 587

if args.delay:
  args.delay = int( args.delay )

if args.attachment:
  if not os.path.isfile(args.attachment):
    print 'Path to attachment ' + args.attachment + ' not found'

if args.emails:
  emailsfile = args.emails
  print 'Emails file: ', emailsfile
else:
  print 'Email: ', args.email

bodyfile = args.body
subject = Header( args.subject, 'utf-8' )
fromheader = args.fromheader

print 'Body text file: ', bodyfile
print 'Subject: ', subject
print 'From: ', fromheader

namematch = re.compile( "\w{2,}\.\w{2,}" )
attachmentmatch = re.compile( 'src="cid:([^"]+)"' )

# Read in body
with open (bodyfile,"r") as file:
  data = file.read().replace('\n','')

# Read in emails
if args.emails:
  with open(emailsfile) as f:
    emails = f.readlines()
else:
  emails = []
  emails.append(args.email)

# Connect
if not args.host:
  server = smtplib.SMTP('localhost')
else:
  server = smtplib.SMTP(args.host, args.port)
  if args.username and args.password: 
    server.login(args.username, args.password)

# Dictionary of used id's
usedints = dict()
randomints = False
intsfile = "randomints.txt"


# Loop over emails
for email in emails:
  if len(email) == 0 or not '@' in email:
    continue  

  msg = MIMEMultipart()

  email = email.strip()
  user = email.split('@')[0]
  name = user
  if namematch.match( name ):
    name = name.replace("."," ").title()
  else:
    name = ''

  if len(name.split(' ')) >= 2:
    fname = name.split(' ')[0]
    lname = name.split(' ')[1]
  else:
    fname = ''
    lname = ''

  # Compile header
  msg["From"] = fromheader
  msg["To"] = email
  msg["Subject"] = subject
  if args.readreceipt: 
    print 'Adding read receipt header: ' + args.readreceipt
    msg["Disposition-Notification-To"] = args.readreceipt

  # Compile body
  body = data.replace("{name}", name )\
    .replace("{fname}", fname )\
    .replace("{lname}", lname )\
    .replace("{email}", email)\
    .replace("{username}", user)\
    .replace("{date}",datetime.datetime.today().strftime("%d/%m/%Y"))\
    .replace("{b64email}",base64.b64encode(email))\
    .replace("{b64remail}",base64.b64encode(email)[::-1])
  

  if re.search("{randomint}",body):
    while True:
      ri = "%d" % random.randint() 
      if not ri in usedints:
        break
    usedints[ri] = 1
    print "Randomint integer: " + email + " : " + ri
    body = body.replace("{randomint}",str(ri))
    randomints = True
    fp = open(intsfile,"a")
    intmail = email + ": Random integer :" + ri + '\n'
    fp.write(intmail)
    fp.close()

  #for captcha images i.e 000001.png
  if re.search("{randomintpadded}",body):
    while True:
      #replace with padded integer for example "000001"
      ri = "%.6d" % random.randint(0,1000)
      if not ri in usedints:
        break
    usedints[ri] = 1
    print "Random padded integer: " + email + " : " +  ri
    body = body.replace("{randomintpadded}",str(ri))
    randomints = True
    fp = open(intsfile,"a")
    intmail = email + ": Random padded integer : " + ri + '\n'
    fp.write(intmail)
    fp.close()


  msg.attach(MIMEText( body, "html" ))
  if args.text:
    msg.attach(MIMEText(html2text.html2text(body),'plain'))

  # Find any embedded images and attach
  attachments = re.findall('src="cid:([^"]+)"',body)
  for attachment in attachments:
    fp = open( attachment, "rb" )
    img = MIMEImage(fp.read())
    fp.close()
    img.add_header('Content-ID', attachment )
    msg.attach(img)


  # Optional attachment
  if args.attachment:
    filename = os.path.basename( args.attachment )
    part = MIMEBase('application', "octet-stream")
    part.set_payload(open(args.attachment, "rb").read())
    Encoders.encode_base64(part)
    part.add_header('Content-Disposition', 'attachment; filename="'+filename+'"')
    msg.attach(part)

  # print msg.as_string()

  # Send email
  sys.stdout.write( "Sending to " + email + "... " )
  sys.stdout.flush()
  server.sendmail( fromheader, email, msg.as_string() )
  sys.stdout.write( "sent\n" )
  sys.stdout.flush()

  if args.delay:
    time.sleep(args.delay)
    
server.quit()

if randomints:
  print "Assigned random ints saved to " + intsfile