Windows 10 too "reluctant" to duplicate display to a monitor via USB-C dock

I am currently using a Dell Precision 5680 laptop, running Windows 10 (it's an image my employer created, I chose neither the OS nor the hardware). My laptop connects to a Dell USB-C-based dock, which in turn has a monitor connected using HDMI. If I boot my laptop disconnected from the monitor, login in, wait for everything to settle, then plug in my dock - the display is duplicated to it, and I'm happy. However, if the computer goes to sleep or hibernates while the dock is connected, then wakes up - typically, the display is not duplicated to the monitor, which stays in stand-by, even though

Question by einpoklum on Super User, licensed CC BY-SA. We show a short excerpt and link to the original thread as credit.