Hi @Crest_Z - just a query on this one - I realise this post is a little aged at this point but I'm having similar issues and have posted something similar within this Community group on a similar issue and wanted to get your insight on something.
I'm having similar issues with the Surface Dock 2 connecting via USB-C to HDMI and some of the online assistance required me to get the latest firmware for Surface Dock 2. At the moment, the Microsoft website that points you to update the firmware is this one:
Download Surface Dock 2 Firmware and Drivers from Official Microsoft Download Center
Note that this site currently shows drivers for almost all Surface devices EXCEPT the Surface Pro 8. This could be the reason why I have issues with monitors not waking up after Surface goes to sleep, but note that almost all other Surface Devices (Laptop, SP 6, 7, even Surface Go) have drivers for them, but when you select any of those MSI files, it fails to install because it requires a particular Surface Pro.
Can Microsoft please attend to this and ensure there are Surface Dock 2 drivers available that are compatible with the Surface Pro 8, as it might be the reason why I am encountering the issues I am.
Thank you in advance - if there is another avenue for resolution here I'm open to that too.
Note, my firmware version for the Surface Dock 2 is 5.202.139
Cheers,
Mike.