DVR - Series recordings not deleting after specified window

I've had an issue for a while now where any series recording I have set up to keep a certain number of episodes is not deleting the episodes.

For example, let's say I record all new episodes of Jeopardy and have it set to "keep the last 3 episodes".  After it records the 4th, 5th, 5th, etc episode, the previous recordings are not getting deleted. I have to do this manually every few days/weeks.  It happens will all series recordings.