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Originally Posted by curiousstranger View Post
My suggested behavior would be for items in non-On Hold parent contexts to not show up when filtering Contexts by On Hold. Is there a downside to that that I'm not thinking of? In what circumstances would you want to see non-On Hold items when filtering by On Hold?
I don't know if there's a downside, as I haven't thought much about it. I think all of my hierarchical on-hold context use has always been in structures where everything is on hold, so it hasn't been an issue (unlike the merged agenda/waiting case above) and I'm a bit hesitant to give a thumbs up or down. That it is hard to come up with a reason why it shouldn't act the way you propose does suggest that any cases where it would break a workflow are probably uncommon, and more people would be helped than inconvenienced by the proposed change.

Fixes for the problem that involve changing OmniFocus are fine, except that they usually don't happen as quickly as anyone who has a real problem would like. That is why most of my suggestions center around finding a way to work with the tools we have (or can make ourselves with Applescript).