Trouble accessing machine every time it restarts

Hey there,
I’m a personal user, just using Duo to secure my headless Windows 10 PC at home that I tend to use via Remote Desktop. I access it via a Windows 10 laptop. Would love your help in solving an issue!

For the past few months, I’ve found that Duo works great until I restart my PC (that has Duo installed). After a restart, I’m able to RDP into the machine like normal, but instead of seeing the Duo screen (where you need to do push verification/text/call) I get stuck at the Windows login screen. I input the (correct) username and password, and get the error “Timeout or other network error”.

Logging into Duo Admin online, I don’t see these login attempts listed.

Sometimes I’m able to fix it by removing and reinserting the ethernet cable. Other times, I’ll need to hook up a monitor/mouse/keyboard to it, and log in directly. Huge pain.

My hunch is that when the PC restarts, it isn’t able to access the internet (and Duo) until someone logs in locally. But I have not been able to troubleshoot it from there.

Thanks in advance for your advice!