I apologize for not mentioning clicking through the security interstitial as I thought this goes without saying. It is understood the page will not load any resources if a person does not accept the security warning and proceed to the webpage. That being said, I did click "proceed" on the security interstitial at one point and Chrome has remembered it since. The CA cert is installed on this particular PC, although I have another test PC without the CA installed. With or without the CA cert installed the security interstitial will appear as the device is accessed using a static IP address over the WAN.
All resources are served from the embedded device, images, fonts, jquery, etc. Regarding the screenshot of the network tab of the developer tool page, there isn't much else to show. The items that failed do not have a response as the connection was aborted by the PC. If there is something specific you would like to see I would be happy to share I just wasn't sure if there was anything else useful. I currently have the device on a static IP address and do not want to post that here. This issue should be pretty easy to replicate with other embedded devices, though. However, to properly replicate the issue you will need to access your device from across the internet.