It seems the gates to the underworld have to remain unprotected for a while. Kerberos, the mighty hellhound, lost his head. All three of them.
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Complete the Hellhound killing task in the Paw and Fur society and report to Grizzly Adams to gain access to Kerberos lair.
Locate and kill the boss, report back to Grizzly for your reward and you will earn the achievement.