Thanks for looking into this. I have no clue why it isn’t bugging on your windows machine. At mine it fails every time I test it. See gifs. Shift-click, control-click - always fails once something is added from the Outliner. I think it failed a few times as well when only adding from the viewport but I don’t have a recording of that and I can’t reproduce it now.
Edit: in third video it also fails when only selecting objects in the Outliner
Windows 10 Pro 10.0.19045 (with latest updates)