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Remote Desktop 2012 R2 - Can't get RD Gateway with RD Web Access working through just 443

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I have one server (2012 r2 fully updated) running all remote desktop roles (RD Web Access, RD Gateway, RD Licensing, RD Connection Broker, RD Session Host) and a separate domain controller.

I have RD Web Access published to cloud.mydomain.co.uk and accessing cloud.mydomain.co.uk/RDWeb works fine.

I want to setup the environment so only port 443 is open from the outside (thus the RD Gateway is installed) and the user can login through RDWeb and click on an app to launch it.

If I leave port 3389 open along with 443 and log on to RDWeb and click the remote app, this works fine.

If I close 3389 on the external firewall and only leave open 443, I can connect AND login to RDWeb but I cannot open the connection

This is expected:
http://i.imgur.com/9j2HRqm.png

Error:
http://i.imgur.com/2LH2c7T.png

Digging in the event viewer yielded: http://i.imgur.com/M9uHm0o.png

Which led me to test change the following setting in the resource access policy, as a test:

http://i.imgur.com/FlGObFr.png

This still didn't work but yielded a different error in event viewer:

http://i.imgur.com/LkaCfU4.png

Now I suspect I have misconfigured something somewhere in terms of the last event where it suggests it can't connect to resource "cloud.mydomain.co.uk" I would have expected this to be the internal FQDN of my session host. Or, I am hitting some sort of odd problem because I have all the roles on the same box.

Any assistance greatly appreciated. I'm keen to find the root cause behind this as I need to document this solution so don't want to invalidate by messing around too much with settings.




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