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Teinaava of the Dark Brotherhood, an old friend of Scar-Tail, gives the Hero a mission to kill him and bring back his heart due to his refusal to carry out an assassination order of the Argonian Royal Court, which is considered the ultimate betrayal by Shadowscales.
Sent to kill him, the Hero finds Scar-Tail, who had already been wounded from fighting off a Shadowscale assassin who was given the same task. Weary of fighting, Scar-Tail offers the Hero a solution that makes everybody happy. They can take Scar-Tail's gold for themselves, give the dead Shadowscale's heart to Teinaava, and allow him to live; or, simply kill him as planned, steal his gold, and return the heart to Teinaava.