When I weaned mine, (once I was completely done - just getting rid of milk supply) I would go as long as I possibly could until it started to hurt to much or I would leak, then I would pump for about 5-10 minutes. Just to get rid of the pain and hardness. Then I would go as long as possible again until it hurt or leaked and do the same think. It took a few days of having to pump, but the intervals between pumping got longer each time, then I wouldn't leak or hurt, but there was still milk, and eventually it dried up. As far as milk in a sippy cup: When I started giving it to my youngest (the only one who protested it at all) I figured out that it was too cold for her. I thought she didn't like the taste, but I noticed one time that if I heated it just enough to take the edge off the fridge cold, she would scarf it. She had been formula fed right before going to milk, so the water was never the same temp as the fridge. That helped her a lot. If you think it's the taste she doesn't like, then when you pump, put what you get in her sippy cup and mix it with a little milk so she still tastes the breastmilk, but gets the new taste of the cow's milk. Eventually she won't protest the difference. That's what I did with my first daughter. My twin boys apparently don't dislike anything so they never protested the milk. They take everything new that we give them. luckily. Anyway. good luck.