Like when ESPN or Hulu show you the same ad for the same bad movie every ad.
In order to execute that buy, the media desk has to make purchases from a variety of platforms. Those platforms also buy and resell inventory from a mix of other places. Segments aren't very well defined, so you end up competing against yourself to buy the same inventory over again.
FWIW, a lot of those OTS services also have very traditional media desks. (e.g., https://nccmedia.com/)