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When our son came home from Russia he was close to 12months. We kept him on the bottle until he was about 18months. His pediatrician recommended it because of his being underweight and anemic. He did sippy cups after that for a while. Sometime between 2 1/2 and 3 we started working on regular cups. Mainly because most preschools want them to be able to drink out of a small cup at least.
For those of you working on switching to regular cups here is a tip passed on to me by a preschool teacher. It worked GREAT for us!! Start the little one off with the small 3-4oz paper/plastic cups. (These are like the ones that go in bathrooms for rinsing after brushing ones teeth.) One brand in our area is DIXIE. They are small so little hands can handle them better. Plus, they don't hold much, so the mess' is small when it happens.
Just an idea I would pass on.
Best of Luck
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