I think I might have stumbled onto something. Yesterday I opened Google Home app on my phone and went into the device settings for both of my chromecast devices. In the privacy section I turned off "send chromecast device usage data and crash reports to Google" then rebooted the chromecast device. After finishing the same for both devices, I then rebooted my Windows 7 machine. After doing so everything seemed to be working fine. No more self signed certificate warnings, the "Cast" button on Chro