sendmail and starttls failing

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From	Michael Grant <mgrant@grant.org>
Newsgroups	linux.debian.user
Subject	sendmail and starttls failing
Date	Sun, 30 Jun 2024 18:00:01 +0200
Message-ID	<IV585-6Io7-1@gated-at.bofh.it> (permalink)
X-Mailbox-Line	From debian-user-request@lists.debian.org Sun Jun 30 15:51:47 2024
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X-Amavis-Spam-Status	No, score=-12.8 tagged_above=-10000 required=5.3 tests=[BAYES_00=-2, DKIM_SIGNED=0.1, DKIM_VALID=-0.1, DKIM_VALID_AU=-0.1, DKIM_VALID_EF=-0.1, FOURLA=0.1, LDO_WHITELIST=-5, PGPSIGNATURE=-5, RCVD_IN_DNSWL_LOW=-0.7] autolearn=ham autolearn_force=no
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X-Virus-Status	Clean
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After an update today, sendmail is refusing to accept mail.  I'm
seeing this in the logs:

STARTTLS=read, info: fds=9/4, err=2

Here's the full log from when I try to send a message through my
server with authentication:

Jun 30 11:42:59 bottom sm-mta[18852]: NOQUEUE: connect from [1.2.3.4]
Jun 30 11:42:59 bottom sm-mta[18852]: AUTH: available mech=DIGEST-MD5 CRAM-MD5, allowed mech=EXTERNAL
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: Milter (clamav): init success to negotiate
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: Milter (spamassassin): init success to negotiate
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: Milter (opendkim): init success to negotiate
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: Milter: connect to filters
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: milter=clamav, action=connect, continue
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: milter=spamassassin, action=connect, continue
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: milter=opendkim, action=connect, continue
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: --- 220 bottom.networkguild.org ESMTP Sendmail 8.17.1.9/8.17.1.9/Debian-2+deb12u2; Sun, 30 Jun 2024 11:42:59 -0400; (No UCE/UBE) logging access from: [1.2.3.4](FAIL)-[1.2.3.4]
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: <-- EHLO [1.2.3.4]
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: milter=spamassassin, action=helo, continue
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: --- 250-bottom.networkguild.org Hello [1.2.3.4], pleased to meet you
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: --- 250-ENHANCEDSTATUSCODES
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: --- 250-PIPELINING
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: --- 250-EXPN
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: --- 250-VERB
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: --- 250-8BITMIME
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: --- 250-SIZE
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: --- 250-STARTTLS
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: --- 250-DELIVERBY
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: --- 250 HELP
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: <-- STARTTLS
Jun 30 11:42:59 bottom sm-mta[18852]: engine=(null), path=(null), ispre=0, pre=0, initialized=0
Jun 30 11:42:59 bottom sm-mta[18852]: tls_srv_features=(null), relay=[1.2.3.4] [1.2.3.4]
Jun 30 11:42:59 bottom sm-mta[18852]: tls_srv_features=empty, stat=0, relay=[1.2.3.4] [1.2.3.4]
Jun 30 11:42:59 bottom sm-mta[18852]: 45UFgx2h018852: --- 220 2.0.0 Ready to start TLS
Jun 30 11:42:59 bottom sm-mta[18852]: STARTTLS=server, info: fds=9/4, err=2
Jun 30 11:43:00 bottom sm-mta[18852]: STARTTLS=server, get_verify: 0 get_peer: 0x0
Jun 30 11:43:00 bottom sm-mta[18852]: STARTTLS=server, relay=[1.2.3.4], version=TLSv1.2, verify=NOT, cipher=ECDHE-RSA-AES256-GCM-SHA384, bits=256/256
Jun 30 11:43:00 bottom sm-mta[18852]: STARTTLS=server, cert-subject=, cert-issuer=, verifymsg=ok
Jun 30 11:43:00 bottom sm-mta[18852]: AUTH: available mech=DIGEST-MD5 CRAM-MD5 LOGIN PLAIN, allowed mech=EXTERNAL
Jun 30 11:43:00 bottom sm-mta[18852]: STARTTLS=read, info: fds=9/4, err=2
Jun 30 11:43:00 bottom sm-mta[18852]: 45UFgx2h018852: <-- EHLO [1.2.3.4]
Jun 30 11:43:00 bottom sm-mta[18852]: 45UFgx2i018852: milter=spamassassin, action=helo, continue
Jun 30 11:43:00 bottom sm-mta[18852]: 45UFgx2i018852: --- 250-bottom.networkguild.org Hello [1.2.3.4], pleased to meet you
Jun 30 11:43:00 bottom sm-mta[18852]: 45UFgx2i018852: --- 250-ENHANCEDSTATUSCODES
Jun 30 11:43:00 bottom sm-mta[18852]: 45UFgx2i018852: --- 250-PIPELINING
Jun 30 11:43:00 bottom sm-mta[18852]: 45UFgx2i018852: --- 250-EXPN
Jun 30 11:43:00 bottom sm-mta[18852]: 45UFgx2i018852: --- 250-VERB
Jun 30 11:43:00 bottom sm-mta[18852]: 45UFgx2i018852: --- 250-8BITMIME
Jun 30 11:43:00 bottom sm-mta[18852]: 45UFgx2i018852: --- 250-SIZE
Jun 30 11:43:00 bottom sm-mta[18852]: 45UFgx2i018852: --- 250-DELIVERBY
Jun 30 11:43:00 bottom sm-mta[18852]: 45UFgx2i018852: --- 250 HELP
Jun 30 11:43:00 bottom sm-mta[18852]: STARTTLS=read, info: fds=9/4, err=2

My cert for bottom.networkguild.org is still valid.  Err=2 is generaly
some sort of file-not-found error, but what file or file descriptor
went bad?

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Thread

sendmail and starttls failing Michael Grant <mgrant@grant.org> - 2024-06-30 18:00 +0200
  Re: sendmail and starttls failing Michael Grant <mgrant@grant.org> - 2024-06-30 18:40 +0200
    Re: sendmail and starttls failing Tim Woodall <debianuser@woodall.me.uk> - 2024-06-30 20:40 +0200
  Re: sendmail and starttls failing Tim Woodall <debianuser@woodall.me.uk> - 2024-06-30 23:30 +0200
    Re: sendmail and starttls failing Michael Grant <mgrant@grant.org> - 2024-06-30 23:40 +0200
      Re: sendmail and starttls failing Tim Woodall <debianuser@woodall.me.uk> - 2024-07-01 00:40 +0200
        Re: sendmail and starttls failing Tim Woodall <debianuser@woodall.me.uk> - 2024-07-01 11:30 +0200
          Re: sendmail and starttls failing Tim Woodall <debianuser@woodall.me.uk> - 2024-07-01 18:40 +0200
    Re: sendmail and starttls failing Tim Woodall <debianuser@woodall.me.uk> - 2024-07-01 00:10 +0200
      Re: sendmail and starttls failing Greg Wooledge <greg@wooledge.org> - 2024-07-01 00:20 +0200
        Re: sendmail and starttls failing Tim Woodall <debianuser@woodall.me.uk> - 2024-07-01 00:30 +0200
          Re: sendmail and starttls failing Mark Fletcher <mark27q1@gmail.com> - 2024-07-01 10:50 +0200
            Re: sendmail and starttls failing Tim Woodall <debianuser@woodall.me.uk> - 2024-07-01 11:20 +0200
            Re: sendmail and starttls failing Greg Wooledge <greg@wooledge.org> - 2024-07-01 13:30 +0200
        Re: sendmail and starttls failing Jeffrey Walton <noloader@gmail.com> - 2024-07-01 00:50 +0200
      Re: sendmail and starttls failing Jeffrey Walton <noloader@gmail.com> - 2024-07-01 00:50 +0200

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