We've always taken a very gentle approach with my daughter in the past and for a few reasons I'm not sure I'm comfortable with leaving her crying with the teacher (even for a few minutes):
1) she is always sensitive, extremely attached to me and slow to transition but if we let her take her time she usually gets there eventually
2) she usually really resists if we push things and I'm worried that we've already made her anxious about preschool and that she'll only resist more
3) she doesn’t 'need' to go to preschool, my main reason was wanting her to get some exposure now so all day kindergarten isn't such a big shock - but I don't want her to have a negative association with school
The problem is that I don't think the preschool will be supportive of my continuing to stay until she finally is ok with me leaving and I wonder if she even will be ok with that given the bumpy beginning we've had. The other major reason is that I'm expecting baby #2 in a month so I can't just go and sit in class with a newborn. I think some of her current stress is also related to her anticipation of the new baby and I can only imagine that part and the separation anxiety could get worse in the coming month.
On the other hand, the teacher said she's concerned that my daughter is getting the message that she isn't capable and I certainly don't want her to feel that either. I am torn... Any advice or thoughts or experience would be greatly appreciated.