Pretty much had to when it was new, and even now that it's well broken in it just makes for a neater look and makes the sail cover go on easier. I do have lazy jacks which help. When alone or shorthanded I put one wrap around the main halyard winch, walk to the aft end of the boom, and lower the halyard 3 ft at a time while flaking and walking forward. (needless to say the Mainsheet is tight so the boom isn't going anywhere). Fast, easy and neat, then I'm onto more serious issues such as what adult beverage will go best with the upcoming sunset