Server 2012 R2 - Remote Apps (RDWeb) and Self Signed Certificates!

Hi all! I have been playing around with VM's on Microsoft Azure just to try and have some Windows Services facing externally that I can play around with and test.
I have spun up a Windows Server 2012 R2 Server and installed Remote Desktop Services on it. I am looking to publish some remote apps and ideally I am looking to get it to work externally.
The Server has been given an IP address which is fine, i have gone to my domain and actually setup cloud.mydomain.co.uk and DNS for this is pointing to the IP address of the server. This is all working and functioning! 
Basically if I go onto my server and connect to the RDweb section and login, i can see my remote apps, i can download the laucher and open them, all works great! :)
If however, I go to https://cloud.mydomain.co.uk/RDWeb it asks me to login, I can then see my remote apps but when I click on them I get a certificate stating that the computer cannot verify the identity of the RD Gateway. 
What am i missing....what do I need to do to get this to work?
If there is some sort of tutorial on how to set this up, fully, from start to finish then that would be great. Otherwise any advice on this would be muchly appreciated!!
Thanks! :)
      

#2 sounds like we would need 2 Essentials servers and we will not have that.
We currently have Server 2008 R2 and have 2012 Standard licenses that are not yet used.
We have much more than 75 users total, but 75 is more than the number of users that will probably take advantage of using RD Gateway any time soon.  It will probably take time to catch on.
If RD Gateway usage was to get super popular and more than 75 users were depending on access to it, then we could financially justify paying to buy all the CALs needed to run RD Gateway without Essentials.  Right now, they are skeptical that it will
be worth spending much money on this and don't want to invest a lot  of money up front.
My understanding is that if we have 75 or fewer users using RD Gateway then we need to by no CALs, just apply a Server Standard Edition License to the server, but if we had 76, we would need to turn off Essentials and buy 76 new CALs.
Or would we need to add 50 CALs to the 25 that automatically come with Essentials?
Also does "turning off" Essentials mean we would have to reinstall and redeploy the RDG or is it just a matter of enabling the RD license server and adding purchased CALs?
No, when you buy essentials you get the right to create 25 users that access the server, when you create the 26th user you will need to have 26 CAL and RDS CAL. 

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