====== Why can't I send mails with Outlook, Outlook Express or Windows Mail? ====== Outlook, Outlook Express and Windows Mail require LOGIN SMTP authentication mechanism. This is disabled by default. Edit /etc/postfix/main.cf and change the line smtpd_sasl_security_options = noanonymous, noplaintext into smtpd_sasl_security_options = noanonymous Now run # /etc/init.d/postfix reload to reload postfix. Test this with # telnet your-server 25 and type ''ehlo client'' Postfix should respond with ... 250-AUTH NTLM PLAIN CRAM-MD5 LOGIN DIGEST-MD5 250-AUTH=NTLM PLAIN CRAM-MD5 LOGIN DIGEST-MD5 ... The AUTH-lines should list PLAIN and LOGIN and Outlook SMTP authentication should work fine now.