Review ChromeOS update 86 (Chromebook Operating System)
I have 3 different USB universal docks (Lenovo,IBM,Targus) and displays stopped working with the latest release of ChromeOS 86 on my Acer 714 Chhromebook. They all use DisplayLink.
The fix was done in Chrome OS 87 and now backported to 86. I recommend you check for updates and if the issue persists, please approach tech support via the contact icon
Dani Long commented
This is just unworkable!!