SSL Cert for Cloudflare for Teams CNAME

General
1

I have an external facing RDWeb website that I just set Cloudflare for Teams in front of. There was a ‘A’ record in DNS and it was deleted to put a CNAME to the same site (A record was rdweb and now CNAME is rdweb). I have the Cloudflare Tunnel working and when you go to rdweb.example.com it takes you to Cloudflare access which authenticates with Azure. After authentication it takes you to rdweb.example.com that has RemoteApps. When trying to access any of these it won’t take the domain credentials, when I revert the CNAME back to the ‘A’ record and point it to the IP address previously I can login to the website and any Apps/Desktop. I’m unsure if I need to purchase a SSL cert for the CNAME that is created? Any help would be appreciated.

Config.yml looks like:
tunnel: TunnelID
credentials-file: C:\Users\USERNAME.cloudflared\TUNNELID.json

ingress:

Catch-all rule, which responds with 404 if traffic doesn’t match any of
the earlier rules

2

Forgot to upload the error I recieve.
RemoteApp Error

3

Is this referring to your localhost?

4

Correct, if I go to localhost:443 on the server it will take me to https://rdweb.example.com

5

Also maybe a question to ask is, is it possible to use Cloudflare for Teams to access RemoteApps through RDWeb or would you need to set this up to directly login to the Terminal server?

6

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