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SSL Certificate question (minor issue)

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I have a Windows 2012 server setup with RDS.  I have about 10 virtual machines already setup - my whole VDI infrastructure.  Everything is working fine - accessing the vm's internally and externally, however, I have issues w/the certificate.

I am using a self-signed certificate (until I can my client to pay for a real SSL cert).

I have created an A record for my DNS at my hosting company that points to my public IP (e.g. remote.mycompany.com instead of typing in the IP address), the port forwarding on my router kicks in and sends the https traffic to my RD Gateway (my Windows 2012) and the user will see the RDWeb page and can log in from there.  The cert is pointed to remote.mycompany.com too.  However, my server is called vdi-remote2.mycompany.com.  Naturally, when using IE to access the RDWeb page, their address bar in IE will be red with the cert error/warning.

First they are greeted with the "There is a problem with this website's security certificate" and will click on continue to the this website.  Upon inspection of the certificate, it will say "This CA Root certificate is not trusted.  To enable trust, install this certificate in the Trusted Root Certification Authorities store."  Ok, I can install it (and have), but I still get the red address bar in my IE.

Needless to say, I'd like to clean this all up.  The users are non-technical people and when they see this stuff, they freak out.  We know what it all means - we're technical folks, but I'd like to clean it all up and just have it nice and security. Green or no address bar when using https in the address bar.

How can I clean this all up though when I have external users accessing https://remote.mycompany.com/rdweb and internal users accessing https://vdi-remote2/rdweb.  I don't recall the possibility to have two certs for one website (the RDWeb).  So, I'm a bit confused on all this cert stuff.  I could keep everything as is and just train the users, but I'd rather not.

Thank you in advance for your reply.


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