Grease the bottom and sides of a 9 x 5 inch loaf pan.
Add yeast and sugar to warm water and let it proof for a few minutes (become frothy - if it doesn't froth your yeast may be too old and your bread won't rise).
Combine 2 cups flour, salt and rosemary in a large bowl.
Add water/yeast mixture, butter and egg. Mix with an electric mixer on medium speed for 3 minutes, scrape bowl frequently.
Add pineapple chunks and remaining cup of flour to form a stiff dough.
Spread batter in pan and shape with floured hands. Cover with plastic wrap sprayed lightly with cooking spray and put in a warm place to rise until doubled, about 1 hour. I like to put mine in an unheated oven with the light on.
Preheat oven to 375℉. Remove plastic wrap from bread. Bake 40-45 minutes, until bread sounds hollow when tapped.
Immediately remove bread from pan and let cool completely on a cooling rack.
In the small bowl of a food processor combine remaining rosemary and pineapple with a few pulses. Add powdered sugar and pulse again until it is mixed and the pieces of pineapple and rosemary are very fine. Add milk a tablespoon at a time until it reaches the desired consistency.