> On Apr 17, 2015, at 07:49, Jan Just Keijser <janj...@nikhef.nl> wrote:
> I don't know - it's not really a TLS cipher that you want, but a TLSv1 
> connection - the nomenclature is overloaded, however.
> It does look like a bug in your local openssl lib, as openvpn 2.3.6 works 
> fine with TLSv1 on CentOS 5, which still uses openssl 0.9.8 . You can also 
> build and link openvpn statically against an OpenSSL (or even PolarSSL) 
> library so that you would not have a second openssl.so file lying around.

  (*le sigh*)  Okay.  So, I’m sorry to say, that I think I’ve been misstating 
things this whole time.  The openssl on my system is in fact 0.9.9.  But, I 
failed to notice that the pkgsrc version of openvpn that I was using had a 
prerequisite for OpenSSL 1.0.1c or later, and I apparently already had such a 
beast on my system.  I dislike having two versions of OpenSSL installed sop 
much that I failed to notice I already did.

  Okay.  So, back to reality.  I took a more full assessment of things, 
uninstalled the older OpenSSL 1.0.1-whatever, the things that had required it, 
and started building the most recent versions of openvpn (2.3.6) and OpenSSL 
(1.0.2a) that pkgsrc has available.

  At this point, I now at least know what OpenSSL and crypto libraries my 
openvpn binary is linked against and can speak more correctly about them.

  So to earlier email about using the openssl s_server and s_client, this time 
with the relevant server-side binary.  It looks just fine.  I can establish the 
connection without error.  I can’t be sure what openssl Tunnelblick is compiled 
with, as it appears to be statically linked against it.  The openssl s_client 
that worked for me just now is 0.9.8zc, but Tunnelblick could be using 
anything.  

  But, the openvpn failure has now changed!  I consider this a success!

Apr 17 11:17:43 bifr?st openvpn[17201]: TCP connection established with 
[AF_INET]A.B.C.D:52232
Apr 17 11:17:44 bifr?st openvpn[17201]: A.B.C.D:52232 TLS: Initial packet from 
[AF_INET]A.B.C.D:52232, sid=34eff6fb 9e28a600
Apr 17 11:17:45 bifr?st openvpn[17201]: A.B.C.D:52232 VERIFY ERROR: depth=0, 
error=unsupported certificate purpose: C=US, ST=Maryland, O=Distal Thoughts, 
CN=client.outside.net
Apr 17 11:17:45 bifr?st openvpn[17201]: A.B.C.D:52232 TLS_ERROR: BIO read 
tls_read_plaintext error: error:14089086:SSL 
routines:ssl3_get_client_certificate:certificate verify failed

  So, my client certificate must be wrong somehow.  I generated it by following 
the commands within the easy-rss scripts, basically.  The following commands 
were used, with an openssl.cnf I’ve had around for a long time and been using 
for other things.  My CA cert pre-existed as well.

% openssl req -days 730 -nodes -new -newkey rsa:2048 -keyout client.key -out 
client.csr -config $PWD/openssl.cnf
% openssl ca -days 731 -out client.crt -in client.csr -md sha1 -config 
openssl.cnf

  Given the error, however, I’m guessing there must be something I’m missing to 
define the “certificate purpose” of my certificate?

                                           - Chris



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