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tom_szabo asked on

How to configure Remote Web Workplace on SBS 2003 with ISA 2000 ...


I need to establishe remote access to a Terminal Server beyond the firewall of a SmallBusiness Server 2003 with ISA 2000. What do I need to do to gain access to this Terminal Server going through the Small Business Server as a firewall/proxy....

Microsoft Server OSSBSMicrosoft Forefront ISA Server

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Philip Elder

8/22/2022 - Mon
Philip Elder

Step 1:
The RWW: http://blogs.technet.com/sbs/archive/2006/07/25/443383.aspx

You need an URL to point to the static IP on your SBS server's external facing NIC (bound to ISA).
Eg: remote.mydomain.com
Required: DNS A Record remote.mydomain.com
 pointing to my SBS IP:
Once you have the DNS settings at your ISP done and pointing to your server, rerun the CEICW and assign the remote.mydomain.com URL as the Internet URL.
Once the CEICW is finished, remote into another machine outside the SBS network if you are not already outside, and open IE and URL: https://remote.mydomain.com/remote and you will be greeted with the RWW logon page.
Standard username and password to access the SBS network from there ... that means make sure that your usernames are formatted FirstLast and you have a good password/passphrase policy in place: Th1s is my p@ssword! (excellent)

Purchase an SSL certificate from a provider that is set to the above remote.mydomain.com URL/common name and install it. That eliminates some of the SBS self-issued certificate hiccups that one runs into for OWA, Windows Mobile, and RDC on Vista.


I am missing something here:
consider my external IP is -> SBS external   = mydomain.com.au
SBS is on: (internal)
TS is on  ( internal)
How will the system know that it has to deal with TS and NOT SBS?
Philip Elder

So, given your example, we have the following at your ISP:
DNS A Record: rww.mydomain.com.au
Points to:
Once that is in place, rerun CEICW to set the rww.mydomain.com.au in place as the RWW URL.
Setup your certificate if you are going 3rd party.
Users open IE and type: https://rww.mydomain.com.au/remote and receive the blue RWW logon page.
They logon and receive the following portal page the RWW Portal (shown below).
In that list they would see the "Connect to my company's Application Server".
They click on that link and SBS takes care of the proxy setup to establish the RDC session.

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James Murphy

Thanks for the above. Is this available in R1 of SBS?
Philip Elder

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Philip Elder

Did you get your hands on the SBS SP1 media prior to their being dropped last December? They include the ISA 2004 update.
If you are looking at upgrading, I highly suggest going with SBS 2003 R2 Premium on Open Value 3 year spread payment agreement. Then there will be a guarantee that MS will cover the setup with an ISA configuration ... yet to be confirmed as far as the how.