On Mon, 14 Feb 2005 16:56:55 +0100, Alexander Dalloz <ad+lists@xxxxxxxxx> wrote: .... As I read the docs (http://www.joreybump.com/code/howto/smtpauth.html) , there should be two ehlo sequences, one prior to TLS, the other post. In the second, sendmail should offer AUTH options. It doesn't seem to be happening: 0[274750]: SMTP Connecting to: ciscy.sterndata.com 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 220 ciscy.sterndata.com ESMTP Sendmail 8.13.1/8.13.1; Mon, 14 Feb 2005 19:50:24 -0600 0[274750]: SMTP entering state: 15 0[274750]: SMTP Send: EHLO [192.168.123.169] 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-ciscy.sterndata.com Hello h-66-167-178-157.chcgilgm.dynamic.covad.net [66.167.178.157], pleased to meet you 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-ENHANCEDSTATUSCODES 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-PIPELINING 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-8BITMIME 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-SIZE 10000000 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-DSN 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-ETRN 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-STARTTLS 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-DELIVERBY 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250 HELP 0[274750]: SMTP entering state: 4 0[274750]: SMTP entering state: 22 0[274750]: SMTP Send: STARTTLS 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 220 2.0.0 Ready to start TLS 0[274750]: SMTP entering state: 20 0[274750]: SMTP entering state: 15 0[274750]: SMTP Send: EHLO [192.168.123.169] 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-ciscy.sterndata.com Hello h-66-167-178-157.chcgilgm.dynamic.covad.net [66.167.178.157], pleased to meet you 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-ENHANCEDSTATUSCODES 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-PIPELINING 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-8BITMIME 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-SIZE 10000000 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-DSN 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-ETRN 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250-DELIVERBY 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250 HELP 0[274750]: SMTP entering state: 4 0[274750]: SMTP entering state: 22 0[274750]: SMTP entering state: 3 0[274750]: SMTP Send: MAIL FROM:<sdstern@xxxxxxxxxxxxx> SIZE=374 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 250 2.1.0 <sdstern@xxxxxxxxxxxxx>... Sender ok 0[274750]: SMTP entering state: 6 0[274750]: SMTP Send: RCPT TO:<sdstern@xxxxxxxxx> 0[274750]: SMTP entering state: 0 0[274750]: SMTP Response: 550 5.7.1 <sdstern@xxxxxxxxx>... Relaying denied. Proper authentication required. 0[274750]: SMTP entering state: 7 0[274750]: SMTP entering state: 12 0[274750]: SMTP entering state: 13 -- Steve