Can't get playback to repeat the correct area

I'm trying to make my score repeat playback of a small section to listen to some details, but for some reason the wrong area is repeated. I select a few measures, then press the repeat button and some blue flags show up at the right place to suggest this area is now repeat. However, when I play it it starts at the wrong place, and it jumps back at the wrong place. Here's a picture where you see me marking the area to repeat, and I've drawn a red ring around the area that's actually played and repeated.