displaylink-debian VS debian-live-config

That is exactly it, proprietary driver. I use https://github.com/AdnanHodzic/displaylink-debian with excellent results with my Pluggable brand USB dock.

The monitor works fine with Windows 10 after I install the drivers. With the Ubuntu, however, things do not work. I tried installing the driver suggested by ASUS specific for this model, the most recent official Display Link driver, and the community script. All have give the same result: installation is said to be successful and asks me to reboot. I reboot and connect the screen. Screen turns on and keeps black. No display is detected. In Additional Drivers there is no drivers listed.

u/marvelggg was correct the issue was DisplayLink. Unfortnuately it wasn't possible to just reinstall their driver because they are not up to date with the current Linux kernel. I used calebanthony's advice from this page to get me back on track;https://github.com/AdnanHodzic/displaylink-debian/issues/745

If you use an Ubuntu or Debian based distro here is a DisplayLink driver: https://github.com/AdnanHodzic/displaylink-debian

(The lenovo branded dock is most horrible especially when used with Linux - needs drivers to be install. https://github.com/AdnanHodzic/displaylink-debian All others just work).

I bought a DisplayLink dock for my ubuntu laptops (2015 XPS and 2021 XPS) and it doesn't really work with either. It's quite maddening.

It requires a strange driver I would've preferred to avoid. I tried a strange workaround on both and neither really works; one still doesn't display through the DisplayPort or HDMI, the other doesn't work with the M.2 2280 built into the dock.

\[0\]: https://github.com/AdnanHodzic/displaylink-debian

Yes it can. Look into to config/archives/ directory (example here, though I only use official repositories for this build, it will work with custom repositories made with aptly) - and section 8.1.5 of the manual.

example config for live-build