My sons the same way and hes 2 almost 3 he wont wake up for one but he insists on 1 or 2 sippy cups of warm milk while laying down to sleep. I ended up buying a sippy cup with a soft top on it, because he wanted a bottle still and I wasnt with that personally at 3yrs old. I have now started giving him his sippy with milk 30 minutes before bed on the couch with me & then telling him this is our bed winding down & that were a big boy and we will have another sippy in the morning. He cried it out a few nights without it but so far so good.
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