What model HT? If they are the ones that lay flat on the ice across the hole, it could be that you need to tighten the tee bar and the top nut, so the reel wont spin without tripping the flag. I always check them before hitting the ice. As far as wind flags, use the bigger notch in the tee bar and that should do the trick, and if not just turn the tip up 90 degrees so the flag is with the wind rather than against it.