N.B. This expects a working sendmail installation with STARTTLS
Install cyrus-sasl # install cyrus-sasl2 cd /usr/ports/security/cyrus-sasl2 make install clean echo "pwcheck_method: saslauthd" > /usr/local/lib/sasl2/Sendmail.conf # install cyrus-sasl2-saslauthd cd /usr/ports/security/cyrus-sasl2-saslauthd make install clean echo 'saslauthd_enable="YES"' >> /etc/rc.conf service saslauthd start Set sendmail make flags Set the following flags in /etc/make.conf (create if it doesn’t exist)
SENDMAIL_CFLAGS=-I/usr/local/include/sasl -DSASL SENDMAIL_LDFLAGS=-L/usr/local/lib SENDMAIL_LDADD=-lsasl2 Recompile sendmail Did you have the source in /usr/src? Otherwise you will need to run the following command. If you don’t use RELEASE-10, you should change that.
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Links qmail.jms1.net BSD Handbook Sendmail.org This expects you to have netcat, perl and openssl installed
Hello without TLS nc mail.server.com 25 220 mail.server.com ESMTP Sendmail 8.14.7/8.14.7; Thu, 11 Sep 2014 12:01:22 +0200 (CEST) > ehlo friendly.server.com 250-mail.server.com Hello friendly [1.2.3.4], pleased to meet you 250-ENHANCEDSTATUSCODES 250-PIPELINING 250-8BITMIME 250-SIZE 250-DSN 250-ETRN 250-AUTH DIGEST-MD5 CRAM-MD5 250-STARTTLS 250-DELIVERBY 250 HELP > quit< 221 2.0.0 mail.server.com closing connection Hello with TLS openssl s_client -starttls smtp -crlf -connect mail.server.com:25 # ...Loads of text here... > ehlo friendly.server.com # ... Same as login without TLS (above) ... Test login $ perl -MMIME::Base64 -e 'print encode_base64("\000coolname\@iix.se\000my-password")' AGNvb2xuYW1lQGlpeC5zZQBteS1wYXNzd29yZA== # .. Log in to server with one of the above ... > AUTH PLAIN AGNvb2xuYW1lQGlpeC5zZQBteS1wYXNzd29yZA== 235 2.0.0 OK Authenticated > quit 221 2.0.0 mail.server.com closing connection Sending mail > mail from: <[email protected]> 250 ok > rcpt to: <[email protected]> 250 ok > data 354 go ahead > From: John <[email protected]> > To: Nobody <[email protected]> > Subject: fnord > > hail eris! > . 250 ok 1113954693 qp 29052 > quit