On 12/27/2013 01:29 PM, Viktor Dukhovni wrote:
On Fri, Dec 27, 2013 at 12:59:11PM -0600, Bobber wrote:

I recently upgraded my companies' mail server to 64 Debian Wheezy. I
am using the Openssl package which is version 1.0.1e-2.

I am having problems when trying to send a message to one of our
business partners.  The SMTP session appears to shut down and it
appears that my server is rejecting their certificate.

Here is the openssl command I am giving to diagnose the problem and
it's output.  Can anyone suggest a solution?  It appears to me that
I may be lacking an intermediary certificate.  How do I fix this if
this is the case?

openssl s_client -CApath  /etc/ssl/certs/ -crlf -starttls smtp
-connect mail.thelawrencegroup.com:25
The posttls-finger(1) utility, included with Postfix 2.11 snapshot
source code, does a much better job of mail server TLS diagnostics.
Their certificate is expired.  Your MTA really ought to log the
error reason.  Consider a better MTA! :-)
I don't see anywhere that it says expired other than this utility. How can I verify that it is really expired? These guys do business with lots of other people but have not noticed anything except with us. The openssl error code 20 indicates an improper intermediate CA from what I can find. Also using this site indicates no problem: http://www.checktls.com/testreceiver.html

Is there another way to verify the expiration?

     $ posttls-finger "[mail.thelawrencegroup.com]"
     posttls-finger: Connected to mail.thelawrencegroup.com[206.16.127.29]:25
     posttls-finger: < 220 mail.thelawrencegroup.com Microsoft ESMTP MAIL 
Service, Version: 6.0.3790.4675 ready at  Fri, 27 Dec 2013 13:13:52 -0600
     posttls-finger: > EHLO amnesiac.example
     posttls-finger: < 250-mail.thelawrencegroup.com Hello [192.0.2.1]
     posttls-finger: < 250-TURN
     posttls-finger: < 250-SIZE
     posttls-finger: < 250-ETRN
     posttls-finger: < 250-PIPELINING
     posttls-finger: < 250-DSN
     posttls-finger: < 250-ENHANCEDSTATUSCODES
     posttls-finger: < 250-8bitmime
     posttls-finger: < 250-BINARYMIME
     posttls-finger: < 250-CHUNKING
     posttls-finger: < 250-VRFY
     posttls-finger: < 250-TLS
     posttls-finger: < 250-STARTTLS
     posttls-finger: < 250-X-EXPS GSSAPI NTLM LOGIN
     posttls-finger: < 250-X-EXPS=LOGIN
     posttls-finger: < 250-AUTH GSSAPI NTLM LOGIN
     posttls-finger: < 250-AUTH=LOGIN
     posttls-finger: < 250-X-LINK2STATE
     posttls-finger: < 250-XEXCH50
     posttls-finger: < 250 OK
     posttls-finger: > STARTTLS
     posttls-finger: < 220 2.0.0 SMTP server ready
     posttls-finger: mail.thelawrencegroup.com[206.16.127.29]:25 Matched 
CommonName mail.thelawrencegroup.com
     posttls-finger: server certificate verification failed for 
mail.thelawrencegroup.com[206.16.127.29]:25: certificate has expired
     posttls-finger: mail.thelawrencegroup.com[206.16.127.29]:25: 
subject_CN=mail.thelawrencegroup.com, issuer_CN=VeriSign Class 3 Secure Server 
CA, fingerprint=58:83:F8:69:1B:45:53:BA:21:36:19:01:B4:C9:7A:A9:54:62:79:57, 
pkey_fingerprint=84:43:0D:55:D9:F8:D3:C5:59:D3:9D:33:42:B3:2E:A4:9B:FE:96:4D
     posttls-finger: Untrusted TLS connection established to 
mail.thelawrencegroup.com[206.16.127.29]:25: unknown with cipher RC4-MD5 
(128/128 bits)
     posttls-finger: > EHLO amnesiac.example
     posttls-finger: < 250-mail.thelawrencegroup.com Hello [192.0.2.1]
     posttls-finger: < 250-TURN
     posttls-finger: < 250-SIZE
     posttls-finger: < 250-ETRN
     posttls-finger: < 250-PIPELINING
     posttls-finger: < 250-DSN
     posttls-finger: < 250-ENHANCEDSTATUSCODES
     posttls-finger: < 250-8bitmime
     posttls-finger: < 250-BINARYMIME
     posttls-finger: < 250-CHUNKING
     posttls-finger: < 250-VRFY
     posttls-finger: < 250-X-EXPS GSSAPI NTLM LOGIN
     posttls-finger: < 250-X-EXPS=LOGIN
     posttls-finger: < 250-AUTH GSSAPI NTLM LOGIN
     posttls-finger: < 250-AUTH=LOGIN
     posttls-finger: < 250-X-LINK2STATE
     posttls-finger: < 250-XEXCH50
     posttls-finger: < 250 OK
     posttls-finger: > QUIT
     posttls-finger: < 221 2.0.0 mail.thelawrencegroup.com Service closing 
transmission channel


--

Bob Wooldridge
bob...@kc0dxf.net
Blog: http://kc0dxf.net/blog/

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