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I used to be a painfully shy kid. I'm still on the quiet side and I HATE anything where I'm the center of attention- seriously....my bridal and baby showers were not so fun because everyone was staring at ME.

I'm also a pre-k teacher. Do your son's teachers ever talk to you about this? Do they have ways to distract him at drop off? Also, does it also affect how he interacts with other children? In my experience, kids usually warm up to their classmates and teachers. It can take awhile (last year I had a student who tried to run away everyday until December), but even my most shy kids will find at least one friend and slowly begin to interact with others. It may help for his teachers to find one of the kids he "trusts" and separate them from the group in the morning (like have them go to one center with less children so he's not as overwhelmed).

I would talk to his teachers and ask what they suggest for kindergarten regarding drop offs. I promise, your son will not be the only one crying! If its possible, I would bring him into the school/classroom before school starts and let him see what it will be like before the emotionally charged first day.

I was extremely shy and probably would have been the crying kid if not for a few things my mom did

- I had non-family babysitters on a somewhat regular basis, so it wasn't a big deal to go with my teacher at the beginning of the school day, I was already used to that.

- Enrolling me in activities with other kids (tee ball, dance, whatever they're interested in) and sometimes staying to watch, sometimes running errands nearby. As long as she stuck around long enough for me to be engaged in an activity I was fine, and soon not even that was necessary.

@Mamaof2: I also taught Pre-K, K, and now teach 2nd. Before the break, how did he do at preschool? I don't really mean drop-off, because lots and lots of kids get upset about that. What do his teachers say about the rest of the day? If he's able to function the rest of the day, even if he's very quite and shy, I don't think there's anything *you* need to do for him.

Have you ever talked with him about why he cries at drop off time? Is he missing you or anxious or scared? I think you should make a plan with him about how to make getting dropped off better: a special activity, a little lovey or small object he can keep in his pocket to reassure him, or a responsibility he could do at school (we had a student who we let set out the art supplies for the day when he arrived).

As for Kindergarten, I wouldn't worry too much. Kids are pretty perceptive & you don't want him to feel like he's doing something wrong when he's upset at drop offs.

My DD is 5.. I don't know if she is painfully shy, but she is definitely shy and reserved. She has been in day care since 5 months so she knows the drill.. but she still has her moments. Such as the time when I came for a Thanksgiving party and she screamed bloody murder when I had to go back to work (that was age 4, this year was perfect). She still has episodes from time to time...

Is there something he can keep in his pocket as a comfort item? Like a little rock that is special or something that he can remember you by? Something not big enough for others to see and embarrass him by.

I'm nervous about my DD going to public school first grade next year.. she is in a very small private school and class right now and I'm definitely nervous about how she will handle the transition, so I feel you!