Server 2008 R2 IIS 7 with Two ISPs & NICs, 1 URL, How to make it work w/Remote Desktop Hosting

A client has a new Windows Server 2008 R2 with IIS 7  server with multiple NICs they want to host a file sharing Web App (Allows authenticated customers to download PDF forms) & Remote Desktop Hosting.
 
It should be available on 2 internet IP addresses, each from a seperate ISP: (example: 1.1.1.1   &   2.2.2.2 )
 
Ideally, I would like to make these services available on both addresses via HTTPS as: https://rd.abdcef.com/pdfs  and https://rd.abcdef.com/rd
 
DNS round robin will NOT work. The client does NOT want to buy another box (example: load balancer)
 
Is there some way to make this work?
 
 
If not, Can the below be made to work?
 
Both services to be available on IP address 1.1.1.1 as https://rd1.abdcef.com/pdfs  and https://rd1.abcdef.com/rd
and
on IP address 2.2.2.2 as https://rd2.abdcef.com/pdfs  and https://rd2.abcdef.com/rd
 
If so how?
Which exact (example: GoDaddy) SSL certificate do I buy ?
zebrasystemsAsked:
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meverestCommented:
Hi,

The only way that you can use both ISP links at the same time is to use DNS (i.e. 'round robin' as you say) - why is that no good in this case?

A load balancer will not provide any benefit in this case anyway - unless it could be hosted in a datacenter somewhere...

yes, you can make your https scheme work fine.  Just two ordinary web server certs are required (one for each hostname) - if you used the dns approach, then you would only need one hostname, and thus only one cert.

Cheers.
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zebrasystemsAuthor Commented:
Hi meverest,

'round robin' causes a user's connection to the server to have a variable destination IP address. This breaks both windows Remote Desktop Services & the file sharing Web App.

"yes, you can make your https scheme work fine"
I hope so.
1) What are the exact steps to I take to make one Windows 2008 R2 IIS 7 web site have two URLs? (example: https://rd1.abdcef.com/pdfs  &   https://rd2.abdcef.com/pdfs )
2) What are the exact steps to take to make Windows 2008 R2 Remote Desktop services have two URLs?
(example: https://rd1.abdcef.com/RD  &   https://rd2.abdcef.com/RD  )
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meverestCommented:
>> 'round robin' causes a user's connection to the server to have a variable destination IP address. This breaks both windows Remote Desktop Services & the file sharing Web App.

but RDC is persistent - it will only connect once and then stay connected.  so it wouldn't matter which one the client connects to first: it will always stay connected to that interface.

>> "yes, you can make your https scheme work fine"
>> I hope so.

I am speaking with confidence on a connectivity level - I can't tell you if your application will remain stable, without a good understanding of how your application works.

>> 1) What are the exact steps to I take to make one Windows 2008 R2 IIS 7 web site have two URLs? (example: https://rd1.abdcef.com/pdfs  &   https://rd2.abdcef.com/pdfs )

you need to make two different web sites - one on each interface.  both web sites can have the root url pointed to the same content, and they can share the same application pool if you want.  then go through the certificate request generation, and certificate install process, for each web site.

>> 2) What are the exact steps to take to make Windows 2008 R2 Remote Desktop services have two URLs?

just make a virtual directory on each of your two web sites, pointed to the same RDC content.

Cheers,  Mike.
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