from smtplib import SMTP

f=file('send_challenge2', 'r')
lngstr = f.read()
f.close()

students = eval(lngstr)

s = SMTP()
s.connect('smtp.webfaction.com')
s.login('myname','simplepass')

t_mes = """\
From: %s
To: %s
Subject: %s

%s
"""

for stud in students:
    TO = [stud[0]]
    s_name = stud[2]
    FROM = stud[0].replace('@UDel.Edu', '@crypto.prof.ninja')
    for i in range(1,6):
        subject = "%s -- BlackHat Challenge %s" % (s_name[1:-1], str(i))
        text = stud[3][i-1]
        message = t_mes % (FROM, ", ".join(TO), subject, text)
        s.sendmail(FROM, TO, message)

s.quit()