Ah!  I understand now! (and need to smack my self in the head)

Jacob's explanation brought me closer to understanding, and your
answer drove it home.  The SSL server/"listener" can only proffer 1
cert per IP.  As ridiculously easy as the explanation sounds, I'm
beginning to wonder why I was being so obtuse about it :)

Yes, my example was not a fair example, because what I was trying to
do did not match the google example I gave.  For the google example,
everything is mail.google.com that it redirects to on the back end.  1
request in brokered out to many on the back end.  I was still missing
the fact that there is no way to have 2 requests in brokered to
different servers on the back end because the receiving host cannot
overlap SSL responders/services on 443 with different certs on a
single web server/IP.

Everyone, thanks for helping me straighten this architecture out
mentally.  I hope it didn't take too much of your time!

On 10/9/08, Miles Raymond <[EMAIL PROTECTED]> wrote:
> Andy,
>
> The key difference between what you are trying to do, and what Amazon and
> Google are doing is that you are trying to have multiple SSL certs on 1 IP
> address.  Amazon and Google have 1 SSL cert on multiple IP addresses.
>
> If you read the pound documentation ( http://www.apsis.ch/pound/ ), you will
> read that:
> "The vital point to notice here is that connection authentication takes
> place BEFORE any request was issued."
> This means that when a connection is made, there is no URL information sent
> until the SSL cert has been verified.  Your server cannot pick and choose
> between different certs to give to the client because all it sees is
> 'connection from x.x.x.x'.  Only AFTER the SSL cert has been sent by your
> server, does the client request 'ok, give me mail.company.com' to the
> server.
>
> In our datacenter, we have an external IP for mail.company.com which is
> different from the external IP for vpn.company.com.  The firewall redirects
> the requests to different ports on our pound server.  Our pound server has a
> listener on 443 for mail.company.com and a listener on 444 for
> vpn.company.com.  Out pound server then balances the request to a multitude
> of back-end servers to actually process the unencrypted request.  The key
> difference between this solution and Jacob Anderson's is that our solution
> has combined the SSL encryption/decryption and balancing in one single
> instance of pound.
>
> -Miles Raymond
> ITI Internet Services
>
> Andy Ray wrote:
>> Thanks Alfonso,
>>
>> That is actually the way we have things configured right now and it is
>> good enough to get by... but my curiosity was peaked when discussing
>> the issue with a colleague about how this is done in the "real world".
>>
>> I just sent a reply to David where I outlined the heart of my question
>> - but basically I can't understand why this is so difficult.  When I
>> access a web address like https://secure.amazon.com or
>> https://mail.google.com I come in through a single IP.  When I look at
>> the cert for mail.google.com, there is no IP information that
>> identifies the site.  If certs were tied to a single IP, how do farms
>> of servers handle a site like https://mail.google.com?
>>
>> The only difference in the solution I'm trying to achieve is that on
>> the back end I only have 1 server instead of 1000 like Google :).
>>
>> Andy
>>
>> On 10/9/08, Andy Ray <[EMAIL PROTECTED]> wrote:
>>> Thank you for your quick reply David!
>>>
>>> So, talking theory here, and trying to better understand the options
>>> available:
>>>
>>> Can the SSL cert be loaded on the router/firewall/gateway device
>>> hosting Pound?  I am assuming that would give Pound access to the host
>>> header in a later request, then the traffic is redirected to the
>>> appropriate internal host?  Or am I way off base here?
>>>
>>> How is this typically handled in a web server farm?  Though I am not
>>> scaling this to anything near that size, I picture this as no
>>> different than accessing https://secure.amazon.com (or other such
>>> address) where the traffic is load balanced/proxied to multiple back
>>> end servers?  Except, for the proxy/load balance on my scale it only
>>> has 1 host behind it.  When I resolve secure.amazon.com I only get 1
>>> IP address - but I'm pretty sure that it doesn't go to 1 host publicly
>>> exposed on the back end at Amazon HQ.
>>>
>>> Thanks for helping me sort it out....
>>>
>>> Andy
>>>
>>> On 10/9/08, Dave Steinberg <[EMAIL PROTECTED]> wrote:
>>>>> What they would like to do is direct mail.company.com:443 to the OWA
>>>>> resources and vpn.company.com:443 to the SSL VPN appliance (two
>>>>> separate internal IP addresses).
>>>>>
>>>>> I understand that the preferred/accepted way for doing this is to
>>>>> obtain multiple IPs from the ISP and map those internally.
>>>>> Unfortunately that is not an option with the provider available in the
>>>>> area at this time.
>>>> Its preferred because most people do not want their
>>>> clients/customers/service users to see SSL validation errors when they
>>>> try to access the service in question.
>>>>
>>>>> From the landing page for Pound, it looks like there is a problem with
>>>>> multiple domain redirection to single internal host IP with virtual
>>>>> servers on that same IP, unless a wildcard cert is used, which seems
>>>>> to indicate that it may be possible if all 443 traffic is redirected
>>>>> to a single host/ip.
>>>> I've not tried it, but yes, a wildcard cert should work.  They are
>>>> unfortunately much more expensive than regular certs.
>>>>
>>>>> From my small understanding of what I've read, Pound (or any other
>>>>> reverse proxy) is unable to decipher the host header because it comes
>>>>> after the SSL tunnel is negotiated.  It would seem that the only
>>>>> solution left would be to use a product like Microsoft's ISA server
>>>>> that does seem to be able to reverse proxy SSL connections.  If this
>>>>> is the case, I'm just a bit surprised that there isn't an option in
>>>>> the *nix world to achieve this goal.
>>>> This is not a software or OS limitation but rather a protocol
>>>> limitation, for the reasons you describe.  It is software agnostic,
>>>> which is why the wildcard cert is the only option that will avoid
>>>> warnings in your client software.
>>>>
>>>> Regards,
>>>> --
>>>> Dave Steinberg
>>>> http://www.geekisp.com/
>>>> http://www.steinbergcomputing.com/
>
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