I can CONFIRM that buying the Microsoft Surface USB-C to HDMI Adapter (https://www.microsoft.com/en-us/p/surface-usb-c-to-hdmi-adapter/94chb2m80s54?SilentAuth=1&activetab=pivot%3aoverviewtab&atc=true&wa=wsignin1.0) fixed the issue for the HP 23es that would not properly connect to the Surface Dock 2 using a Uni USB-C to HDMI cable (https://uniaccessories.io/products/usb-c-to-hdmi-cable-3ft-6ft-10ft) which is the exact same cable that my 27 inch Sceptre Curved monitor is using with the same dock and no issues.
I can use the same cable to plug the HP 23es directly into my Surface Book 3 and it will connect perfectly. However the Surface Dock 2 seems to have an issue with "older" monitors (the HP 23es came out in 2016) so it only seems to want the adapter.
As much as I love Surface products I am pretty disappointed right now. I should not have to buy a $50 adapter to make my $200 dock work when there are already cables that serve the same purpose as this adapter.