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SimonS avatar Server

How to stop RD-Gateway from redirecting to HTTP

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SimonS

I have a single server setup for my Remote Application Services. So one server is RD-Gateway, Connection Broker, and Host all at once.

I'm trying to use a Cloudflare Tunnel as a proxy with the following ingress rules (ws for websocket):

ingress:
  - hostname: rdp.domain.com
    service: ws://SERVERNAME

I can connect via rdp.domain.com and successfully see the IIS default page. However, if I try rdp.domain.com/rdweb/ I get a ERR_TOO_MANY_REDIRECTS error. But the URL changes to rdp.domain.com/RDWeb/Pages/

Cloudflare has an article about this which lists possible causes. One thing I do use is a Full (Strict) Encryption mode for my domain. The article suggests that my Server possibly redirects HTTPS to HTTP which could cause the issue because it loops basically forever.

When I try to connect to go to rdp.domain.com/rdweb/ and have Wireshark running on the RD-Gateway Server, I see a lot of those in a loop (around 20 of these entries) - .248 is the IP Cloudflare Tunnel uses to communicate, .226 is my RDP Server:

1589    26.863255   10.0.0.248  10.0.0.226  HTTP    1133    GET /rdweb HTTP/1.1 
1590    26.864954   10.0.0.226  10.0.0.248  HTTP    403     HTTP/1.1 302 Found  (text/html)
1591    26.875477   10.0.0.248  10.0.0.226  TCP     60      53360 → 80 [ACK] Seq=37246 Ack=12216 Win=2102272 Len=0

I can't exactly say what this means. however the -> 80 makes me think it wants to redirect to HTTP?

I have the following questions:

  • How can I continue to dig into this issue to really find out what happens?
  • If the problem is that the server redirects to port 80, can I tell my RD-Server to really only use HTTPS and Port 443, and not use 80 at all?
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