Satwik Nadkarny's questions

I need to host multiple sites on same domain in IIS (local). I have two sites :

1. Site 1
2. Site 2

Both have different root folders and one is a CMS application (Site 1) while the other is a pure HTML site (Site 2).

I need to host it as such :

www.mytestsite.com (Site 1)
www.mytestsite.com/childtestsite (Site 2)

I can get the first one working by making the necessary changes in the host file. However, as I understand, I need to host the Site 2 on a different port in IIS. Due to this, I am unable to use the host file. So, what would be the best way to get this working?

I configured a website (DotNetNuke website) on IIS 8.5 having Windows Server 2012 R2 operating system on port 85. I accessed the website using http://localhost:85 and the website worked well. Then, I added another binding to the website in IIS with respect to IP address so that I could access it as 192.168.5.187:85. However, I am unable to access it via the IP address as I get an error page. Specifically, I get a "404 Not Found error page".

On further investigation, I found that the website works on only one port - 85. Whenever I change the binding to point to a different port, the website doesn't work(gives a 404 Not Found error). The current site binding is

IP Address      Port
    *            85

and the website works fine. If I change this binding to

IP Address      Port
     *           83 (infact anything other than 85)

the website doesn't work.(gives a 404 Not Found error)

To summarize:

1. The website does not work when I add a binding having the IP address. (gives a 404 Not Found error)

2. The website does not work on any port other than 85 when using localhost. (gives a 404 Not FOund error)

I am having a hard time understanding this so can somebody help me out as I need this website to be accessible via the IP address.