I am using the wordnet API from nltk.
When I compare one synset with another I got None but when I compare them the other way around I get a float value.
I don't think it is a bug in wordnet per se. In your case, automobile is specified as a verb and car as noun, so you will need to look through the synset to see what the graph looks like and decide if the nets are labeled correctly.
A = 'car.n.01'
B = 'automobile.v.01'
C = 'automobile.n.01'
wn.synset(A).path_similarity(wn.synset(B))
wn.synset(B).path_similarity(wn.synset(A))
wn.synset(A).path_similarity(wn.synset(C)) # is 1
wn.synset(C).path_similarity(wn.synset(A)) # is also 1