How's everybody doing? My work-from-home setup involves a Macbook Pro, a CalDigit TS3+ dock, two external displays (one in portrait, one in landscape), and a couple other peripherals. Since getting the TS3+, I've noticed that OSX screws up the orientation of the external displays ~50% of the time. This inevitably results in me furiously tilting my head sideways while I try to maneuver the mouse pointer onto the Mac Display preferences for that display and fix it before my first meeting of the day starts.
I found a Stack Overflow solution that works for me. I downloaded the free Display Rotation Menu tool from Mage Software and now I can just click and change the orientation from the system menu. Should be part of the OS in these WFH days!