>250-AUTH DIGEST-MD5 CRAM-MD5 >250-STARTTLS A lot of the time applications either have a default configuration or are hardwired to only offer "insecure" SASL mechanisms when session encryption (like TLS) is being used. Why don't you try: openssl s_client -connect smtp-server:smtp-port -crlf -starttls smtp Do a EHLO, and see what is being offered as SASL mechanisms then. --Ken