Web Application Proxy: Connection over HTTPS not working

E

egremy

Hello,

About 5 weeks ago I did not know anything about Windows Server 2016, reading and practicing I managed to create my ADFS and my WAP server, but I am having some problems.

I have configured the Web Application Proxy component in a Windows Server 2016 to publish applications to the internet. The purpose of this is to authenticate users using SAML.
I have been able to publish a couple of applications using the Remote Access Management tool, the problem I have is that my published applications are not accessible anywhere.


I tried to access the External URL of my published applications from the internet, without success. First, if I try the URL with HTTPS, I receive a message that says: This site can't be reached (This is my main problem).

I need to clarify some doubts that I have and I hope you can help me.

  • The communication between WAP & ADFS are over HTTPS (using the port 443). The connection between WAP and Internet, does it have to be HTTPS?
  • According to a question named Windows 2016 Firewall Blocks Port 80 for Web Application Proxy (sorry for not paste the link. My account is not verified yet, so I am unable to use links and images in the body of the question), I have to open the port 80 (and redirect all traffic to 443) to allow all connections. I did it and the message changed from This site can't be reached to 503 Service Unavailable. But this is using HTTP instead of HTTPS. It this a problem or is the correct way to configure the Windows Server (WAP)?
  • I installed the ADFS Certificate in my WAP server to make it reliable (for ADFS). Also my WAP server is in the same Domain Controller as my ADFS. The certificate that I installed is enough to provide the HTTPS certification for WAP (In case it is needed)?

As a note:

  • I am using Cloudflare to get the DNS of my WAP & ADFS server. The configuration only allow HTTPS between the Browser and Cloudflare. Hence if I go to my WAP server using my DNS (HTTPS) it fails. But if I access using the IP address (HTTP) it looks like the server responds with the 503 Service Unavailable.
  • Both servers (WAP and ADFS) are virtual machines in Google Cloud Platform


I have followed several tutorials but some are very different from others even if they are to achieve the same goal. I have read the documentation about Windows Server 2016, but I have found it incomplete and confusing. Also some documents redirect me to Windows Server 2012/2012R2 and I do not know if the information is the same or is an error.

Any help you can provide me with this will be helpful. Thank you,

René Egremy.

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