I have tested and concur that this is a bug when using the "On a Day" required expression it moves from false to true on the specified day but doesn't more from true to false when the specified day passes.
I will note that "Between two dates" where the days are the same but using the optional times does work at least for a subset of the day. I didn't try to specify a time of 12:00 am for the start and 11:59 pm for the end.