Why can't contacts enter this campaign more than once?

I have a very simple campaign that I want to recipients to be able to enter more than once. The email itself is quite complex with variable data and field merges and the same recipient may receive far different emails on different occasions. I have added a filter in the segment to keep anyone from receiving the email more than once every two weeks. The campaign is set to run from today to the end of the year. This is the entire setup on the campaign canvas:

Segment --> Email

I have check the box in the Email step that says "Allow emails to be re-sent to past recipients". I have check the box in the campaign settings that says "Allow contacts to enter the campaign more than once." And I have told the Segment to check "Hourly until campaign is deactivated" in the Segment.