Package: sendmail-bin
Version: 8.14.3-9.1
Severity: important

Sendmail logs the following:

Apr 28 03:02:04 castro sm-mta[3225]: NOQUEUE: connect from localhost [127.0.0.1]
Apr 28 03:02:04 castro sm-mta[3225]: o3S324GI003225: Milter (mimedefang): init 
success to negotiate
Apr 28 03:02:04 castro sm-mta[3225]: o3S324GI003225: Milter: connect to filters
Apr 28 03:02:04 castro sendmail[3224]: STARTTLS=client, relay=[127.0.0.1], 
version=TLSv1/SSLv3, verify=FAIL, cipher=DHE-RSA-AES256-SHA, bits=256/256
Apr 28 03:02:04 castro sm-mta[3225]: STARTTLS=read: 3225:error:0D0C50A1:asn1 
encoding routines:ASN1_item_verify:unknown message digest 
algorithm:a_verify.c:146:
Apr 28 03:02:04 castro sm-mta[3225]: STARTTLS: read error=generic SSL error 
(-1), errno=11, get_error=error:00000000:lib(0):func(0):reason(0), retry=99, 
ssl_err=1

This appears to be because the certificate used for localhost uses
sha512 as a message digest.  Sendmail does not call
OpenSSL_add_all_algorithms(), which causes OpenSSL not to find the
relevant algorithms.  You can see the relevant OpenSSL bug report at
<http://rt.openssl.org/Ticket/Display.html?id=2197&user=guest&pass=guest>.

Sendmail should probably call OpenSSL_add_all_algorithms().
-- System Information:
Debian Release: squeeze/sid
  APT prefers unstable
  APT policy: (500, 'unstable'), (1, 'experimental')
Architecture: amd64 (x86_64)

Kernel: Linux 2.6.32-4-amd64 (SMP w/2 CPU cores)
Locale: LANG=en_US.UTF-8, LC_CTYPE=en_US.UTF-8 (charmap=UTF-8)
Shell: /bin/sh linked to /bin/dash

-- 
brian m. carlson / brian with sandals: Houston, Texas, US
+1 832 623 2791 | http://www.crustytoothpaste.net/~bmc | My opinion only
OpenPGP: RSA v4 4096b: 88AC E9B2 9196 305B A994 7552 F1BA 225C 0223 B187

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