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Guess what! I think I figured it out. I just wasn't seeing this.

The context view I was looking at was based on a custom project perspective in which not all of the active projects in view were highlighted. When I made sure they were all highlighted in the project view, it showed up in the context view.

The highlight aspect is something very subtle and I was just not seeing.

So in the end, it WAS user error. Now that I get the distinction of highlighting, I will be more aware of what I'm highlighting in the future.