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Our daycare uses open cups past 18 months. I would work to transition him to those. But if you or daycare don't think he is ready, I'd just let him use a sippy there since he'll probably use an open cup soon. I wouldn't worry about him learning to use a sippy at 21 months - it's easy and shouldn't present a problem for him. I wouldn't push the issue if it were me.

My daycare uses sippies as well but I only used straw cups with DS1 and the munchkin 360 cup with DS2. I used to send them to school with them. They told me that they would keep them and wash them along with all of the other sippies. I know that they both don't/didn't get their correct cups but it wasn't a problem. Both boys were able transition between all kinds of cups. I don't think it's wrong to push it if it's important to you but in my experience, it's not a deal breaker.

I would ask if it's ok if you can send a straw cup but if they say no I wouldn't be too worried about it. It's not like his abilities are going to regress, and you can work with him on going to open cups at home.

I feel like using a sippy is better practice for an open cup anyway, since it needs to be tipped. Straw cups notoriously leak more than sippy cups also. This just doesn't seem like a big deal to me.

Our old daycare was like this. However, my kid did not understand sippies and they put him into an absolute rage. He started daycare at 16 months and I just sent straw cups with his name on them in masking tape. He only ever drank water there anyway. He finally "got" sippies at like 2 year old, when he started mastering open cup, so it was a moot point.

@macintosh: You know what is best for your kid but alas, the very first lesson we all learn in daycare is we definitely lose an element of control over our kids lives. I learned quickly that daycares have an established routine and a reason for what they do and babes learn to adapt. They really do. Pick your battles with daycare bc you will probably have bigger ones than sippy cups!