how many settling session will he have, we had 3, 15mins, half hour then hour. 1st one I had to collect her due to being upset but the next 2 times she was ok. I just think kids will cry because it's so overwhelming for them but it's upto the staff to bond with them and reassure them to help them settle in, it's what they are trained to do. my lg started Monday and upto now she's been happy going in and coming out.
I would say yes you should continue. They see this all the time and he probably did cry a bit but if he was able to recover from it, in their minds he probably was ok because they probably see worse. This is a normal adjustment and after some time he will probably love it. My daughter runs into nursery and when I told her she was going back to nursery after the Easter break her face lit up. It’s really hard at the start when they are unhappy but you do need to give it time.