Thanks Chris,
 that seems to connect but sends no data back? The error is
 3074385544:error:1409E0E5:SSL ... :ssl handshake failure:s3_pkt.c:637
Returns:

CONNECTED(00000003)
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 0 bytes and written 0 bytes
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
SSL-Session:
    Protocol  : TLSv1
    Cipher    : 0000
    Session-ID:
    Session-ID-ctx:
    Master-Key:
    Key-Arg   : None
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    Start Time: 1482460650
    Timeout   : 7200 (sec)
    Verify return code: 0 (ok)
---
 I was trying to do something I thought was very standard.

 So, is this "an evolving standard" issue?  Is it something I have done
with keytool when producing a csr?  It is obviously not just openssl that
takes issue with TLS handshakes.  Is it just java in general? Or should I
be getting back to my certificate provider with a specific request? Change
provider?

P

On 22 December 2016 at 18:41, Christopher Schultz <
ch...@christopherschultz.net> wrote:

> -----BEGIN PGP SIGNED MESSAGE-----
> Hash: SHA256
>
> Peter,
>
> On 12/22/16 12:52 PM, Peter Wallis wrote:
> > Ahh! changed the server.xml entries to 8443 tried: openssl s_client
> > -connect 192.168.1.149:8443 and got: CONNECTED(00000003)
> > 3074541192:error:140790E5SSL routhines:SSL23_WRITE:ssl handshake
> > failure:s23_lib.c:177: --- no peer certificate available --- No
> > client certificate CA names sent --- SSL handshake has read 0 bytes
> > and written 295 bytes --- New, (NONE), Cipher is (ONE) Secure
> > Renegotiation IS NOT supported Compression: NONE Expansion: NONE
> > ---
> >
> > That might mean something (note I retyped it from a ssh connection
> > after a stiff drink so there may be typos)
>
>
> Perfect. The problem is that openssl s_clinent defaults to an SSLv2
> "hello" handshake and not a TLS handshake, which is more appropriate
> in this day and age.
>
> Try this:
>
> $ openssl s_client -tls1 -connect 192.168.1.149:8443
>
> - -chris
>
> > On 22 December 2016 at 16:27, Christopher Schultz <
> > ch...@christopherschultz.net> wrote:
> >
> > Peter,
> >
> > On 12/22/16 11:03 AM, Peter Wallis wrote:
> >>>> Hi Christopher, re 443 on *nix; yes, set AUTHBIND='yes' in
> >>>> /etc/defaults/tomcat8
> >
> > Okay. Are you sure you've got that configured properly? Try
> > changing port 443 to 8443 in server.xml and bouncing Tomcat. Let's
> > try to solve one problem at a time.
> >
> >>>> re openssl s_client -connect on a different machine; it times
> >>>> out
> >>>>
> >>>> Did have a thought -- one that might not be obvious to you
> >>>> experts -- I am serving that page via No-IP dynamic dns.
> >>>> Their support people are "cagey" about whether this works or
> >>>> not (they don't answer the question and suggest I buy an
> >>>> upgraded service)  I believe people who know what they are
> >>>> doing just run their own dns using unbound?  If that makes no
> >>>> sense, please ignore; I don't know what I'm talking about but
> >>>> it seems we are looking for something I've done that is
> >>>> weird.
> >
> > Let's try this: what's the actual IP address of your pi?
> > 192.168.0.10 or somesuch?
> >
> > Change your port from 443 -> 8443 and then try this:
> >
> > $ openssl s_client -connect 192.168.0.10:8443
> >
> > If that connects and shows the cert, then your TLS configuration
> > is correct. It will complain about the hostname (IP address) not
> > matching the cert's CN, but that's okay).
> >
> > Since you have lots of moving parts, let's find out what's working
> > first and then fix whatever problems remain.
> >
> > -chris
> >
> >>>> On 22 December 2016 at 15:38, Christopher Schultz <
> >>>> ch...@christopherschultz.net> wrote:
> >>>>
> >>>> Peter,
> >>>>
> >>>> On 12/22/16 2:43 AM, Peter Wallis wrote:
> >>>>>>> Hi Christopher, so it seems I have done something
> >>>>>>> exceptional :-) Thanks for taking a look...
> >>>>>>>
> >>>>>>> <Connector port="443"
> >>>>>>> protocol="org.apache.coyote.http11.Http11NioProtocol"
> >>>>>>> maxThreads="150" SSLEnabled="true" scheme="https"
> >>>>>>> secure="true" keystoreFile="/home/peter/.keystore"
> >>>>>>> alias="tomcat" keystorePass="changeit"
> >>>>>>> clientAuth="false" sslProtocol="TLS" />
> >>>>
> >>>> This looks fine except for one thing: you are using port 443
> >>>> on a *NIX system which requires you to either run as root
> >>>> (bad) or make other arrangements. Have you made such
> >>>> arrangements?
> >>>>
> >>>>>>> Keystore type: JKS Keystore provider: SUN
> >>>>>>>
> >>>>>>> Your keystore contains 2 entries
> >>>>>>>
> >>>>>>> Alias name: gandi Creation date: 21-Dec-2016 Entry
> >>>>>>> type: trustedCertEntry
> >>>>
> >>>> Okay, that's your CA.
> >>>>
> >>>>>>> Alias name: tomcat Creation date: 21-Dec-2016 Entry
> >>>>>>> type: trustedCertEntry
> >>>>
> >>>> Okay, that's presumably your server's cert.
> >>>>
> >>>>>>> Owner: CN=alexa.proseco.co.uk, OU=Gandi Standard SSL,
> >>>>>>> OU=Domain Control Validated
> >>>>
> >>>> If that's your site name (alexa.proseco.co.uk) this looks
> >>>> good.
> >>>>
> >>>> What happens if you do this from the outside (e.g. not on the
> >>>> pi itself) :
> >>>>
> >>>> $ openssl s_client -connect alexa.proseco.co.uk:443
> >>>>
> >>>> -chris
> >>>>>
> >>>>> ------------------------------------------------------------------
> - ---
> >>>>>
> >>>>>
> >
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> >>>>>
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