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wasabi2k: What exactly are you trying to achieve?
Multiple websites with SSL on a single IP? Why?
ISA/TMG is end of life and won't do what you want it to.
You can do it with URL Rewrite and ARR but it's pretty ugly.
http://www.iis.net/learn/extensions/url-rewrite-module/reverse-proxy-with-url-rewrite-v2-and-application-request-routing
Why do you want to do this?
wasabi2k: What exactly are you trying to achieve?
Multiple websites with SSL on a single IP? Why?
ISA/TMG is end of life and won't do what you want it to.
You can do it with URL Rewrite and ARR but it's pretty ugly.
http://www.iis.net/learn/extensions/url-rewrite-module/reverse-proxy-with-url-rewrite-v2-and-application-request-routing
Why do you want to do this?
Web Application Proxy, new to Windows Server 2012 R2, may also fit the bill: http://technet.microsoft.com/en-us/library/dn280944.aspx
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Regs: If I understand your issues correctly, I believe that ISA/TMG would work, and it will be supported for a while yet. Web Application Proxy, new to Windows Server 2012 R2, may also fit the bill: http://technet.microsoft.com/en-us/library/dn280944.aspx
when you say 'legacy app with no ssl support' - does it use a bunch of hard-coded URLs instead of relative paths? If so then url-rewrite might be required.
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