How to enable SMTP AUTH with FreeBSD default Sendmail 1) Add the following to /etc/make.conf: # Add SMTP AUTH support to Sendmail SENDMAIL_CFLAGS+= -I/usr/local/include -DSASL=2 SENDMAIL_LDFLAGS+= -L/usr/local/lib SENDMAIL_LDADD+= -lsasl2 2) Rebuild FreeBSD (make buildworld, ...) 3) Make sure that the pwcheck_method is correct in Sendmail.conf. Sendmail.conf (${PREFIX}/lib/sasl2/Sendmail.conf) is created by the cyrus-sasl2 ports during installation. It may have pwcheck_method set to saslauthd by default. Change this to what is appropriate for your site. 4) Add the following to your sendmail.mc file: dnl The group needs to be mail in order to read the sasldb2 file define(`confRUN_AS_USER',`root:mail')dnl TRUST_AUTH_MECH(`DIGEST-MD5 CRAM-MD5')dnl define(`confAUTH_MECHANISMS',`DIGEST-MD5 CRAM-MD5')dnl define(`confDONT_BLAME_SENDMAIL',`GroupReadableSASLDBFile')dnl 5) Add the following before FEATURE(msp) in your submit.mc file: DAEMON_OPTIONS(`Name=NoMTA, Addr=127.0.0.1, M=EA')dnl This disables SMTP AUTH on the loopback interface. Otherwise you may get the following error in the log: error: safesasl(/usr/local/etc/sasldb2) failed: Group readable file when sending mail locally (seen when using pine locally on same server). ---- 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 and will cause your users to enter their passwords each time they retreive their mail (NS 4.7). The DONT_BLAME_SENDMAIL option GroupReadableSASLDBFile is needed when you are using cyrus-imapd and sendmail on the same server that requires access to the sasldb2 database. SASLv2 support of Sendmail is starting with 8.12.4.