Jay It might require having quite a few filters applied. Although I swear I’ve seen it even in a totally ‘naked’ Pane, now that you’re asking for repro I (of course) can only make it happen again in heavily-filtered ones.
A couple months back I converted to a system that uses progressively more-filtered Panes (Outline, Group-By: none) to generate my workflow. It’s mostly awesome but this means some of my Panes have 4 or even 5 filters applied (including the usual hide-completes one).
Try this combo, for example:
It also appears to happen while zoomed-in a few levels, with (only) the default no-completes filter.
When it doesn’t work, it tends to apply to deeper-level parents but just plain ignore top- and second-tier parents. If I manually collapse the ‘stubborn’ ones and then use the button again, they tend to behave – but if I switch away and then back to that Board, the bad behavior repeats.