User blog comment:KillRoy231/Bobby's deal with Crowley - Plot hole/@comment-74.132.82.188-20180717165611/@comment-74.132.82.188-20180718155409

I understand that the Hellhounds traditionally kill those who survive the full length of their contracts with the Crossroads Demons; but if they don´t survive it and die early, they still go to Hell.

I was speculating that, when a person dies early like Bobby did, a Hellhound still comes to collect the soul. One of the  Hellhounds´ duties could be to work for the Crossroad Demons, making sure the soul is delivered directly to the actual demon who made the contract. And since there were no Hellhounds there, Bobby´s soul was never delivered directly to Crowley, so the contract was never fulfilled.

But I admit that this is rationalization. I think it is more likely a genuine mistake on a writer´s part. Bobby´s concern for his soul made for a nice segue into the reveal of Souless Sam a few episodes later.