Guess Ruby forgot to mention the freaking hellhounds!
Yeah, it would seem.

These two unnamed hellhounds served the demon Ruby as guards of the Occultum.


At some point, these two hellhounds came into the possession of Ruby who left them to guard the abandoned church where she had hidden the Occultum. Even after Ruby was killed by Dean Winchester, the hellhounds continued their duty.

In 2020, after learning of the Occultum's location from Ruby in the Empty, Castiel leads the Winchesters and Jack to the church, though the group noted that it seemed too easy. Hearing barking nearby, they quickly realized that hellhounds were guarding the church and barricaded themselves inside with Sam attempting to hold the door shut against them. Though Ruby had given Castiel very specific instructions on how to find the Occultum, she did not tell him about the guarding hellhounds. As a result, Dean suspected that like Anael, Ruby had just been trying to kill them.

As Jack returned from the Garden of Eden in the form of a golden orb, the hellhounds finally broke in. The orb released waves of energy, briefly rendering the hellhounds visible before disintegrating them.

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