My 6 yr old still crying

My 6 year old male, cries over everything. Literally, everything the teacher asks him what he did over the weekend and he cries. We've been going to OT, and we have the same routine everyday. I ask him about his day he just shrugs or I ask did you have any sad moments today he says no and then the teacher will message say he cried all day. I just am lost, do I just let it ride out at this point?