To anybody interested, Here is how to configure Stunnel for Outlook Express v6 in Windows XP to work: Modify Stunnel configuration to this: [cox-pop3] client = yes accept = 127.0.0.1:110 connect = pop.cox.net:995 CAfile = ca-certs.perm OCSPaia = yes [cox-smtp] client = yes accept = 127.0.0.1:25 connect = smtp.cox.net:587 CAfile = ca-certs.perm OCSPaia = yes Now configure Outlook Express as follows: Set incoming mail(POP3) to 127.0.0.1 Set outgoing mail(SMTP) to 127.0.0.1 Have "Logon using secure password authentication" unchecked. Have "My server requires authentication" unchecked For POP3 set incoming mail (POP3) to port 110. For SMTP set outgoing mail (SMTP) to port 25. Have "This server requires a secure connection(SSL)" for POP3 unchecked. Have "This server requires a secure connection(SSL)" for SMTP unchecked. Everything works except I have the following error message in the Stunnel log: "Service [service name] needs authentication to prevent MITM attacks" Does anybody know how to prevent this from happening? I tried having the "My server requires authentication" checked but I still have the message when Stunnel starts. Thank you for any help.