How to enable SMTP AUTH with FreeBSD default Sendmail 8.11 1) Add the following to /etc/make.conf: # Add SMTP AUTH support to Sendmail SENDMAIL_CFLAGS+= -I/usr/local/include/sasl -DSASL -D_FFR_UNSAFE_SASL SENDMAIL_LDFLAGS+= -L/usr/local/lib SENDMAIL_LDADD+= -lsasl 2) Rebuild FreeBSD (make buildworld, ...) 3) Create /usr/local/lib/sasl/Sendmail.conf with the following. pwcheck_method: pwcheck 4) Add the following to your sendmail.mc file: TRUST_AUTH_MECH(`DIGEST-MD5 CRAM-MD5')dnl define(`confAUTH_MECHANISMS',`DIGEST-MD5 CRAM-MD5')dnl define(`confDONT_BLAME_SENDMAIL',`GroupReadableSASLFile')dnl define(`confRUN_AS_USER',`root:mail')dnl ---- Additional AUTH Mechanisms are LOGIN, PLAIN, GSSAPI, and KERBEROS_V4. These can be added to TRUST_AUTH_MECH and confAUTH_MECHANISMS as a space seperated list. You may want to restrict LOGIN, and PLAIN authentication methods for use with STARTTLS, as the password is not encrypted when passed to sendmail. LOGIN is required for Outlook Express users. "My server requires authentication" needs to be checked in the accounts properties to use SASL Authentication. PLAIN is required for Netscape Communicator users. By default Netscape Communicator will use SASL Authentication when sendmail is compiled with SASL. The DONT_BLAME_SENDMAIL option GroupReadableSASLFile is needed when you are using cyrus-imapd and sendmail on the same server that requires access to the sasldb database.