Speakers are not working under Bootcamp

Are there any unknown devices in Windows Device Manager?

What is the current W10 version installed?

JohnnyCasino99 wrote:

From what I can deduce the Cirrus Logic drivers are incompatible with the latest version of Windows 10.

That should not be the case! It would create a lot of problems on quite a few Macs.

Do the same headphones work properly when you are booted in macOS?

2018 Macs use the Apple T2 Controller, while 2017 Macs do not. Your Cirrus controller is expected.

Can you post screen shots similar to what I have posted from your Mac with your headphone connected?

JohnnyCasino99 wrote:

Do you think reinstalling Windows would help at this point? My feeling is that it wouldn't change anything.

No.

Can you Eject/Disconnect the CalDigit TB3 physically leaving only the headphones connected to your Mac and test your headphones with a direct connection?

If you disconnect the headphones and leave the CalDigit disconnected, do your built-in speakers work properly?

Do you have a Playback and Recording tab in Sound preferences with just the headphones connected?

The process is the same, irrespective of the booted OS.

How to reset the SMC of your Mac - Apple Support

Reset NVRAM or PRAM on Mac - Apple Support

I have an old Apple TRRS headset which seems to work fine.

This is the headset.

What is the year/model of your Mac (do not post the serial number)?

Your Cirrus drivers are still installed. Do they show any errors? What brand/type of headphones do you use?

Your headphones would show up under the main Dock connection. What happens if you connect the headphones directly to the 3.5mm audio jack on the Mac.