Webster is a dog that is too cool for school. When he is taken to a farm rescue group, Webster knows that he will escape at his first available opportunity. Webster has become cynical in terms of loving families. He has been to too many houses where the families have treated him terribly. At the rescue, Webster is given a comfortable bed with home-baked treats. He meets Jack, the Terrier and Florence, the bossy cat who seems to run things around the farm.
When a storm crashes a tree into the fence, Webster (or Bad Hat, as he likes to be called) sees his opportunity for his breakout. Webster thinks that he is alone, until he keeps running into other animals from the farm. Webster, who always wanted to be an outlaw, starts to see himself as a good guy. He learns what it means to have a real family.