Hi and thank you for using Petco Pet Education Center, formerly Petcoach! Max is adorable! It is very common for puppies to lose multiple teeth, not just both upper canines at once. My own puppy lost 8 teeth in one night! As they lose teeth, they may bleed a little bit, so do not be alarmed if you see a little bit of blood on anything they chew. It will resolve pretty quickly. Good luck!