I'm running into a problem with Sendmail trying to implement SMTP- auth. I"m running 8.14.5 and have saslauthd running under FreeBSD 7.0-R. I don't believe I have starttls enabled (but I also compiled a version with it and have been testing it too - same problem) - just looking for basic auth, but am wondering if my configuration is not compatible with modern mail clients? I don't think I have any certs set up. It seems an older version of Microsoft Outlook Express works fine with SMTP-auth with no problems, but Outlook 2010 won't work, and neither will Eudora (basic settings to not use encryption and use same uid/pw as pop3 account name) When trying to send mail the server reports: "550 571 Relaying Denied. Proper authentication required." Is there some config that I am missing? Why does it work with Outlook Express but not other e-mail clients? my site.config.m4 has: APPENDDEF(confENVDEF',-DSASL=2') APPENDDEF(conf_sendmail_LIBS',-lsasl2') dnl APPENDDEF(confLIBDIRS',-L/usr/local/lib/sasl2') APPENDDEF(confLIBDIRS',-L/usr/local/lib') APPENDDEF(confINCDIRS',-I/usr/local/include') My sendmail.mc has: define(ConfAUTH_OPTIONS',A') TRUST_AUTH_MECH(LOGIN PLAIN')dnl define(ConfAUTH_MECHANISMS',`LOGIN PLAIN')dnl My /usr/local/lib/sasl2/Sendmail.conf has: pwcheck_method: saslauthd When I restart sendmail this shows up in the logs: Jun 16 12:36:24 x sm-mta[79090]: restarting /usr/sbin/sendmail due to signal Jun 16 12:36:24 x sm-mta[81145]: starting daemon (8.14.5): SMTP+queueing@00:30:00 Jun 16 12:36:24 x sm-mta[81147]: STARTTLS=client, relay=mxgw1.mail.nationalnet.com., version=TLSv1/SSLv3, verify=FAIL, cipher=DHE-RSA-AES256-SHA, bits=256/256 Jun 16 12:36:24 x sm-mta[81148]: STARTTLS=client, relay=mxgw1.mail.nationalnet.com., version=TLSv1/SSLv3, verify=FAIL, cipher=DHE-RSA-AES256-SHA, bits=256/256 testing on the cmd line: telnet localhost 587 Trying 127.0.0.1... Connected to localhost. Escape character is '^]'. 220 xxxt ESMTP Sendmail 8.14.5/8.14.5; Fri, 15 Jun 2012 18:28:03 -0500 (CDT) ehlo localhost 250-xxxx Hello localhost [127.0.0.1], pleased to meet you 250-ENHANCEDSTATUSCODES 250-PIPELINING 250-8BITMIME 250-SIZE 250-DSN 250-AUTH GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN 250-DELIVERBY 250 HELP I am not using any certs or ssl right now - just trying to get basic auth to work. Anyone have any ideas?