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I agree - that's what it should do. Only: it doesn't do that in my case.

In Planning mode, I have the grouping filter set to ungrouped, the sorting filter set to flagged, the action filter set to "All" and the time and flag filters set to all as well.

Well: my firstmost project is one with a flagged item (so far so good - almost), but then I have 14 projects without any flags; the 15th is again one with flags. Yet the flags aren't the firstmost actions given in the list (nor is the the list sorted on due dates): in the first and the 17th project list first unflagged items, and the flagged ones appear later.