xfce4-display-settings not always showing popup windows

Upon initially connecting new displays, xfce4-display-settings pops up (when "Show dialog" is enabled). However it won't always show the popups identifying the displays, even after clicking "Advanced". Toggling "Show popup windows" off and on again makes them show up.

This can be confusing when the user has multiple monitors of the same model.

This only happens when attaching displays, it doesn't seem to happen when starting xfce4-display-settings --minimal manually.

xfce4-settings-4.19.0

Thanks!