I see this problem too -- ironically from a freshly installed wheezy
system running sendmail. Syslog:
<20>1 2013-05-16T09:00:24.888014+02:00 duva sm-mta 19115 - -
STARTTLS=client, error: connect failed=0, SSL_error=5, errno=0, retry=-1
<21>1 2013-05-16T09:00:24.888257+02:00 duva sm-mta 19115 - -
ruleset=tls_server, arg1=SOFTWARE, relay=bugs-master.debian.org,
reject=403 4.7.0 TLS handshake failed.
<22>1 2013-05-16T09:00:24.888318+02:00 duva sm-mta 19115 - -
r4G70JEv019092: to=<702...@bugs.debian.org>, delay=00:00:04,
xdelay=00:00:02, mailer=esmtp, pri=150610, relay=bugs-master.debian.org.
[140.211.166.26], dsn=4.0.0, stat=Deferred: 403 4.7.0 TLS handshake
failed.
The attempts and failures happens repeatedly, and the mail is stuck on
the queue:
r4G70JEv019092 224 Thu May 16 09:00 <si...@josefsson.org>
(Deferred: 403 4.7.0 TLS handshake failed.)
<702...@bugs.debian.org>
Sendmail doesn't seem able to recover (like postfix did) so it just
re-tries the delivery and TLS handshake and never fall back to non-TLS.
Thus, I can't seem to get any emails through to bugs.debian.org without
the following in /etc/mail/access and running 'make' in /etc/mail.
Try_TLS:master.debian.org NO
Try_TLS:bugs-master.debian.org NO
/Simon
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