I also have a (once) very timid child who just completed 1st grade. I didn't want to send him off to school, either, fearing that he wasn't ready socially. As parents, we tend to coddle our children long after they require it, often hurting their chances at ever breaking out of that shell. My advice is that you send him, the teacher will let you know within the first few weeks if maybe perhaps you should withdraw him and wait another year or so. When my son was in Kindergarten, he began biting his fingernails as a nervous habit, which stopped as soon as school was out. And though he was shy at first and sometimes when I walked him in I had to help him get set up with a partner for morning activities, once I was gone and the day started, he always settled in quite nicely and had a good time with his friends. It's important for him to have the opportunity to be around other children his own age and interact with them, learning coping skills and the right way to respond to people who (annoy) him, which he will get at school. My son cried through Kindergarten graduation because there were so many people there and he was nervous in front of them all, and the fact that everyone looked at him because it was so cute only intensified the fact! But, he made it through, and the first day of first grade, he went willingly and without a thought about how shy he could be. One thing we did for first grade though, was we went and met the teacher individually before we started school, so he felt like he knew someone before he started, which I think helped, so if you can, meet with his teacher and talk and have her talk to him. A lot of growth will happen over that Kinde-first grade summer that will help him be more comfortable. Blessings in your endeavors!