This may sound basic, but have you verified that the firewall on the server is 
set up to allow communication from the client? I think Ubuntu's firewall 
rejects all traffic to ports that don't match what its installed and configured 
packages claim they run on, without external configuration.

-Kyle H

On September 18, 2014 6:02:16 AM PDT, espe...@oreillyauto.com wrote:
>
>I have an ubuntu 14.04 with openssl 1.0.1f-1ubuntu2.3 server running
>and a
>another server connecting as the client with ubuntu 12.04 with openssl
>1.0.1-4ubuntu5.16.  I am getting an error about the TLS handshake
>failing
>i/o timeout.  I have tried using our internal wildcard certs on both
>servers since I already have that on my web server , aka - the client,
>and
>I generated a sif signed cert on the server and copied it to the
>client.
>Both produce the same results.
>
>On the server I took a tcpdump and then did an ssldup of that file and
>this
>is what I am seeing for every connection:
>
>210 1 0.0012 (0.0012) C>S Handshake
>ClientHello
>Version 3.1
>cipher suites
>TLS_RSA_WITH_RC4_128_SHA
>TLS_RSA_WITH_3DES_EDE_CBC_SHA
>TLS_RSA_WITH_AES_128_CBC_SHA
>TLS_RSA_WITH_AES_256_CBC_SHA
>Unknown value 0xc011
>Unknown value 0xc012
>Unknown value 0xc013
>Unknown value 0xc014
>compression methods
>NULL
>
>I have looking through posts trying to find an answer with no luck yet.
>Any and all help is appreciated.
>
>Thanks,
>Eric Speake
>Web Systems Administrator
>O'Reilly Auto Parts
> (417) 862-2674  Ext. 1975
>
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