http://tools.ietf.org/html/rfc2821#section-3.2 BB doesn't wait for the server to send 220 some servers delay the 220 to trap badly written clients (typically spammers) they block BB too :( sendmail,c near the comment "wait for initial server OK" the comments sugggest that changes to the TLS code are needed before this can be fixed :(
Fixed in git: commit 34c469ae0495bb010969eb920c63d31ed4a0e793 Author: Denys Vlasenko <vda.linux@googlemail.com> Date: Sun Sep 18 03:01:49 2011 +0200 sendmail: don't talk until 220 code is seen. Closes 3487 Will go into 1.20.x Unfortunately, the fix affects only the mode without -H 'comm helper', since we don't know whether comm helper is a program which does STARTTLS and therefore eats code 220...