the combination of your second and 4th screen shot will trigger automatic printing.
But the screen shot is from the condition record, not the the PO message, and it is only a part of it, so we cannot know if this is the only condition record that you have and if this one was found with the data you have in your PO.
the screen shot from the PO messages shows all in green, means all have been processed, nothing is sitting unprocessed. Maybe someone else took the copies from the printer before you were able to take it.