Through the Fringe of Madness The Hero , when first entering the portal on the island in the Niben Bay after being briefed by Haskill at the end of A Strange Door , will come to the town of Passwall ( after being introduced to the first Shivering Isles hostile in the game thus far , a leveled Grummite ) . Overview . In town , the Hero will find two characters talking , the mayor of Passwall and a dark elf . Both are a little beyond ecstatic , and when asked about The Gatekeeper they will say that he is finishing off some adventurers " just now " . If following them to the gate , they will see a hulking , stitched - up mass of flesh with a sword attached to one arm butchering a crowd of warriors . The captain , who is watching until the Hero approaches , explains that they can " take it from here " , and after all of his men are subsequently killed , he forsakes his bravado and flees for his life , all the way back to Cyrodiil . The Gatekeeper , however , instead of attacking the throng assembled to watch , simply moves back to his spot in front of the Gates of Madness . The Hero then finds out that The Gatekeeper has the keys to the Gate sewn into his flesh , and although the majority of the citizens of Passwall wish to make it into the Shivering Isles , they cannot - no one is able to kill The Gatekeeper and the Gates can not be opened even if they could sneak by . Walkthrough . Speak to Jayred Ice - Veins . Speak to Jayred Ice - Veins who can be found either in his house or in the local tavern ( Follow the map marker ) . He wishes to kill the Gatekeeper himself . He helps the Hero to retrieve the bones of a former Gatekeeper from the Gardens of Flesh and Bone . There they encounter a few Shambles , which Jayred helps to kill . Jayred will then retrieve the bones of the dead Gatekeeper and make arrows out of them . Speak to Jayred in a few hours to receive the arrows . These " Gatekeeper Bone Arrows " are powerful , and have a negative effect on the current Gatekeeper . Speak to Nanette Don . Talking to the apprentice of the Necromancer Relmyna Verenim , who will inform them that the Necromancer ' s tears themselves harm the Daedra trapped within the Gatekeeper . If they poison their bone arrows ( or any other weapon for that matter - the monster simply has a very large amount of health , causing even Umbra to be near ineffective ) with these tears , then they will cause extra damage to The Gatekeeper , allowing him to be taken down . Relmyna Verenim . Sneak into Relmyna ' s room inside The Wastrel ' s Purse and read the " Note to Sherogorath " and it will say they should follow her at night to see where she goes . She will go and visit the Gatekeeper and she will drop a handkerchief . Pick it up and squeeze the tears into a bottle . Visit Jayred to see if he has the arrows ready . The Gates of Madness . When the arrows are ready , use one dose of the tears on them and proceed to the Gate . Either go alone or enlist Jayred to help with killing him . When the Gatekeeper is dead , take both keys to Mania and Dementia . Walk through either Gate into the Isles . After The Gatekeeper is disposed of , the members of Passwall ( the town built at the Gates of Madness ) will eagerly enter the gates , Jayred taking the lead . Relmyna , however , is furious with the Hero for killing her " child " , but does not cause any other trouble for the player .