> We'd put the pills in the wet dog food and he'd just eat it up.
This may be a problem. Medication generally does not taste good, and may be putting him off of the food altogether.
Rather than medicating their food, I prefer to use these with our dogs:
http://smile.amazon.com/GREENIES-POCKETS-Original-Canine-Treats/dp/B001BSBFUO
They turn medication time into treat time. :)
Deal link: Amazon
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Normal food wouldn't work for me either, but pill pockets work like magic. It completely encloses the pill and my dog chews and swallows the whole thing. https://www.amazon.com/Greenies-POCKETS-Chicken-30-count-vet-recommended/dp/B001BSBFUO