Windows 10 machine causing SSL errors to server on same network.

Here is a weird one that I can't figure out. I'm self hosting my personal site over my gigabit internet connection at my home. The server is running on a rasp pi 2, with Apache and wordpress with SSL cert's from let's encrypt. My site runs https natively.

The raspi is set on the DMZ port of the router and is reachable via DDNS, and I have the a records pointing to the DDNS so it forwards on whenever the IP dynamically changes.

My website runs great, but I have another machine on the same network that run's window's 10. Whenever this machine is on my site becomes unreachable, generating SSL errors from windows media sharing. On my mac, it will point to the mac's internal SSL certificate of that local machine. It's only when this windows 10 machine gets turned on. The moment I turn it off I get timeouts on the website until I reboot the router. Once I reboot the router everything runs great again.

I have confirmed that the IP addresses are not the same. I initially thought it was an IP address conflict causing the issue. I really don't understand why this is happening. I have over 50 devices on my network and this particular machine with windows 10 is the one causing the issue as it only happens when it's turned on. It's really weird. Any ideas or suggestions?