Sorry, but the mailing list program has eaten more than half of my rant. Looks like it doesn't like a dot on it's own on a line (Yes, I know it's the SMTP signal for EOT).
Hi, I was monkeying around a bit with s_client. Idea is to feed s_client a file with commands required to STARTTLS, authenticate to the smtp server and the message itself. I have this file: ------------------------------ ehlo hereami auth login dfbdffdbZWhhcjU= dffbbbbdddBoYTI= mail from:<here...@gmail.com> rcpt to:<here...@gmail.com> data From: <here...@gmail.com> To: <whoe...@gmail.com> Subject: With s_client Date: Mon, 18 Feb 2013 22:28:00 +0100 Testing ... one-single-dot QUIT ------------------------------- Without the dashes, of course; plus real addresses and passwords. I then do openssl s_client -crlf -connect smtp.gmail.com:587 -CApath /etc/mutt_CA -starttls smtp -pause -quiet < feed gmail then comes back with depth=2 /C=US/O=Equifax/OU=Equifax Secure Certificate Authority verify return:1 depth=1 /C=US/O=Google Inc/CN=Google Internet Authority verify return:1 depth=0 /C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com verify return:1 250 ENHANCEDSTATUSCODES 250-mx.google.com at your service, [91.44.157.56] 250-SIZE 35882577 250-8BITMIME 250-AUTH LOGIN PLAIN XOAUTH XOAUTH2 250 ENHANCEDSTATUSCODES 334 VXNlcm5hbWU6 and that's it, nothing more. Won't take any more interactive input either. The 334 VXNlcm5hbWU6 is begging for the user name, but apparently it doesn't get one. Now comes the funny thing: leaving out the ehlo line in the file gives me depth=2 /C=US/O=Equifax/OU=Equifax Secure Certificate Authority verify return:1 depth=1 /C=US/O=Google Inc/CN=Google Internet Authority verify return:1 depth=0 /C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com verify return:1 250 ENHANCEDSTATUSCODES 334 VXNlcm5hbWU6 334 UGFzc3dvcmQ6 Final words are now 334 UGFzc3dvcmQ6 which means it's awaiting the password. The thought would arise that somehow s_client for whatever reason only gets the first two lines from the external file. Typing the commands interactively wotks ok. I tired all sorts of other things, like leaving out -pause etc, but to no avail. Anybody has any clues, please ("bug or feature")? TIA, regards Andreas ______________________________________________________________________ OpenSSL Project http://www.openssl.org User Support Mailing List openssl-users@openssl.org Automated List Manager majord...@openssl.org