I've had to use meds on nice and easy cats and very hard cats.I think if you put the pill pusher in his mouth quick right in the center a bit further than you'd like pointing down his throat and quicky disperss it may help.I had to do that with 1 difficult cat.I did it fast and put that pill pusher right down his throat(Not really) but almost.I hate to say it that way but it worked for me.I hold the scruff of the neck too.His fur..... not his neck.I never hold their face or neck...it's too dangerous.Just the fur on the back of his neck gently.But it seems to work.Good Luck