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It sounds like you have a due date in October set on that action. OmniFocus treats that as an item that starts in May and ends in October, not one that will repeat every day between May and October. When you check that item off completed, a new item will be generated with start and due dates one day later.

If you want the action to appear in the Due perspective, you'll want to change the due date to fall within whatever "Due Soon is in the next" period you've chosen in the Data pane of preferences. (For a task you want to do every day, you'll probably want matching start and due dates, with the former happening in the morning, and the latter sometime before bedtime.)

Hope this helps!