I always use the peanut butter trick, put some on your finger for the dog to lick off, put a ton on the pill - half a dollar sized pill will probably require a ton - open mouth and insert pill and have dog lick all the peanut butter off you finger, hand or what ever. Works for Rotts, my 68lb. dog and toy dogs. It is so sticky and they are so busy licking, they don't realize they have swallowed anything. With a pill that size you it may work better if you break it in at least half. Keep a separate jar just for giving pills. Dogs love peanut butter, I use crunchy, I think it diguises the pill. Worth a try. Let us know if anything works.