Okay, now I got you.
Actually, there was a discussion about this more than a year ago - this behavior is supposed to be a feature! The point is that it is hard to say how long a recording is (especially when it is changed by the secretary) and the redirect should not kick in during the annoucement. Therefore the decision was to redirect after the annoucement is over.
In your case that might a problem, as you repeat the annoucement several times. But IMHO it is still reasonable to say if the caller did not do anything during these three annoucements that you redirect him after a relatively short time to a operator, for example after 0 seconds.