import smtplib def prompt(prompt): return raw_input(prompt).strip() fromaddr = prompt("From: ") toaddrs = prompt("To: ").split() print "Enter message, end with ^D (Unix) or ^Z (Windows):" msg = ("From: %s\r\nTo: %s\r\n\r\n" % (fromaddr, ", ".join(toaddrs))) while 1: try: line = raw_input() except EOFError: break if not line: break msg = msg + line print "Message length is " + repr(len(msg)) server = smtplib.SMTP('smtp.live.com:25') server.set_debuglevel(1) server.sendmail(fromaddr, toaddrs, msg) server.quit() I'm trying to send an Email using that example, but it doesnt work, I dont get any error it just doesn't send anything, I'm trying to send it to a hotmail email. Any help will be appreciated, Thanks.