On 17/04/15 17:22, Chris Ross wrote:
>> 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?
>

this is indeed an entirely different error; I'd suggest to generate your 
certificates using the easy-rsa scripts; most likely what you're missing 
is the X509v3 purpose flag - you can verify this using
   openssl x509 -text -noout -in client.crt

You should see something like
         X509v3 extensions:
             X509v3 Basic Constraints:
                 CA:FALSE
             Netscape Comment:
                 Easy-RSA Generated Certificate
             X509v3 Subject Key Identifier:
                 [...]
             X509v3 Authority Key Identifier:
                 [...]

             X509v3 Extended Key Usage:
                 TLS Web Client Authentication
             X509v3 Key Usage:
                 Digital Signature


HTH,

JJK


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