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D'oh, I failed to notice that both the project and the context that the action was assigned to was on hold. Since the project is on hold, actions from that project aren't going to show up in context view regardless of what context they're in. An on-hold project is basically in deep-freeze.

You haven't dropped it entirely, but you're really not planning on working on it any time soon.

If you make the project active again, the action will show up in context view as you're expecting.