Ok, I've solved this problem. So for anyone else who has it, here is the solutions. Though, I must say, this has been a very frustrating experience. Once you know the issue it's really obvious. But without knowing before hand it's like a needle in a hay stack. On the Primary Server node in Configuration Manager Console, right click, properties. Select the Site Mode tab. Click on specify Root CA Certificates. Make sure that lines up with the Web Site certificate you specified for the IIS SCCM Website. Note, this certificate requires document signing. You will need to export this certificate from the certificate authority as a binary with a .cer extension before you can add it. If anyone is having trouble with this application, drop me a message. I'm planning on spending a fair bit of time on this software and it's always good to have a network of people working with this technology for those times when you get stuck! Regards, -Ashleigh Green