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Is it possible to use a single port for SSTP and an IIS website, or will I be required to set up separate ports? I've got Server 2008 R2, and I tried doing it but now I can't get IIS to serve anything out of 443 even with RRAS uninstalled.

This is for a small home network, and I ideally want to open up just port 443 on the router and nothing else..

Any suggestions?

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If you can get 2 IPs, it will be much easier. With SSL, it's difficult to have 2 sites using the same IP and port.

It is possible though. To do so you'll need to setup host headers over SSL. Here's a search that returns a number of good results.

Essentially, you'll need to use a single cert for both sites. For plain HTTP it's easy. Just add a host header for your website and leave SSTP with the empty host header.

As for why 443 doesn't work for you now, it sounds like there may be a software (i.e. windows firewall) or hardware firewall in front of your web server. See if it works from the local machine. If it does, then it's a firewall issue. If it doesn't, then it's not configured correctly in IIS.

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