Hi, Ok, I have a bit more information, and maybe a better lead... Facts: 1) I upgraded my laptop from FreeBSD 5.4 to 5.5 2) The upgrade in #1 upgraded my sendmail from 8.12.10 to 8.13.6 3) My version of cyrus-sasl is 2.1.22 4) I use Authinfo type M of "DIGEST-MD5" to a Smarthost (DS) What I've learned is that if I send small messages, its fine. If I send larger ones, it fails ... I see : Jun 14 08:29:40 vjofn sm-mta[3232]: DIGEST-MD5 server step 1 Jun 14 08:29:40 vjofn sm-mta[3232]: DIGEST-MD5 server step 2 Jun 14 08:29:40 vjofn sm-mta[3232]: no user in db Jun 14 08:29:40 vjofn /kernel: Jun 14 08:29:40 vjofn sm-mta[3232]: no user in db Jun 14 08:29:40 vjofn sm-mta[3232]: AUTH=server, relay=c-69-249-95-97.hsd1.nj.comcast.net [69.249.95.97], authid=tuc, mech=DIGEST-MD5, bits=128 Jun 14 08:29:41 vjofn sm-mta[3232]: Incorrect Sequence Number Jun 14 08:29:41 vjofn /kernel: Jun 14 08:29:41 vjofn sm-mta[3232]: Incorrect Sequence Number Jun 14 08:29:41 vjofn sm-mta[3232]: k5ECTe51003232: collect: premature EOM: Unknown error: 0 Jun 14 08:29:41 vjofn sm-mta[3232]: k5ECTe51003232: SYSERR(root): collect: I/O error on connection from c-69-249-95-97.hsd1.nj.comcast.net, from=<t...@xxxxxxxxxxxxxxxxxxxxxxxxxx> Jun 14 08:29:41 vjofn /kernel: Jun 14 08:29:41 vjofn sm-mta[3232]: k5ECTe51003232: SYSERR(root): collect: I/O error on connection from c-69-249-95-97.hsd1.nj.comcast.net, from=<t...@xxxxxxxxxxxxxxxxxxxxxxxxxx> Jun 14 08:29:41 vjofn sm-mta[3232]: k5ECTe51003232: from=<t...@xxxxxxxxxxxxxxxxxxxxxxxxxx>, size=28301, class=0, nrcpts=1, proto=ESMTP, daemon=MSA, relay=c-69-249-95-97.hsd1.nj.comcast.net [69.249.95.97] If I change the Authinfo M type to "PLAIN", its fine. So where do I look to resolve this? Thanks, Tuc