Azure VM's running RDS Gateway - SSL configuration

Hi all,

I'm having problems understanding the SSL configuration required in Azure for a RDS deployment. Everything's configured on my VM's and I'm trying to give access to the outside world to the Gateway Server on port 443 using a third party certificate.

I've uploaded the certificate as a PFX to the certificate section on the cloud service, I haven't done anything other then this at this point.

When connecting to the gateway with the RDP client I get the error

"This Computer can't verify the identity of the RD Gateway [Server Name]. It's not safe to connect to connect to servers that's can't be identified. Contact your network administrator for assistance."

This is because when hitting the service it's still using the built in Azure SSL certificate.

I've seen some suggestions that I might need to replace the cert thumbprint ID on the endpoint I've created but all the documentation I can find seems to be on web apps etc. with the config being performed in Visual Studio. Can anyone give me some clear direction on this?

Thanks in advance,

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David Johnson, CD, MVPOwnerCommented:
did you setup azure networking before creating these vm's? on the gateway server you have to open up port 443
Virtual Machine Endpoint in the virtual machine you have to add the ssl certificate and configure the RDP gateway to use it and not here
mbaldoAuthor Commented:

Thanks for the post, the end point has been created and the third party certificate has been used in the remote desktop/gateway configuration.

When I attempt to connect to port 443 however the certificate that is presented is still the azure certificate.
David Johnson, CD, MVPOwnerCommented:
are you using the gateway ip address or the vm's publc ip address? Did you setup networking BEFORE you created the vm's ????
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mbaldoAuthor Commented:
Yes, I've created a VLAN and all VMs are within a cloud service, I'm connecting to the public IP address of the cloud service. An endpoint has been created on the gateway server on port 443.
mbaldoAuthor Commented:
Sorry, turns out it's all my fault!

I'd used the IP of a second cloud service I'd setup in the DNS for the custom domain, corrected this and all working fine. Apologies for any time wasted!

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mbaldoAuthor Commented:
my mistake, David's suggestion prompted my to check the basics :(
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