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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