What is surprising is that I have never really had to deal with this with Josiah, the last time I remember Josiah having any hint of separation anxiety was when he went to daycare. This didn't even start at the beginning of school instead it started midway through the term.
So it began one week I was dropping Josiah off at school and all of a sudden he tells me he is sick, he says it fifteen times I think it was. But he hadn't mentioned it before school had begun. So I decided that I needed to allow him to stay at school and let the school contact me if he still is sick when I leave. I spoke to him about how sometimes when we are scared we feel sick, stayed with him for a minute. It was so bad I needed to go without saying goodbye he wasn't going to let me leave. He screamed and cried and they had to take him outside to get him to calm down. I stayed for a little bit, called from the car-park (I know it sounds far fetched) to make sure everything was fine. And he was, then I called at lunch time just in case and he was fine. I picked him up and he was just fine.
The next day I was onto it more and he was again scared and crying and not wanting me to go, I picked him up and sat him on the teacher's aide's lap and left without turning back. Told him I was leaving and when I was going to be back and that he can be a brave boy. This whole situation lasted for the whole week and it was very difficult to leave him, it got to the point that the bell would ring and he would promptly burst into tears.
Luckily this is not the end of the story, but it did lead to a lot of soul searching. In each situation I had the choice to nurture or to rescue my son. I was well within my rights to take him home and rescue him but it would have lead to many things and could set up a lifestyle of dependence for him. Did I feel guilty you bet I did, did it hurt? Of course it did, did I cry at all, you betcha! But I realized that just because they are crying does not mean they are in danger, they are suffering from anxiety and they are seeking reassurance but they are indeed safe even if they don't know it yet.
Fast forward another few weeks and he is just fine now still a little anxious when we drop him off. Turns out he might have been a bit nervous from getting pneumonia and asthma so now he is well he has calmed down. Not something that I want to experience anytime soon but for now things have settled for him.