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Should you have done a little sacrificing in the belly of the Temple of Shadows, then this quest becomes available to you after reaching the Westcliff camp at the end of the Road to Westcliff quest. Fast-travel to the Temple of Shadows, where Cornelius Grim declares that it's time for you to "prove your allegiance to the forces of darkness." You're to kill every living soul in Oakfield, period.

Accept a chance at becoming a truly malevolent member of the temple, then fast-travel to Oakfield and speak to Wicked Wilbur. The two dark monks have already barricaded the city's exit, so you simply have to meander through the town killing all 37 of its citizens. You'll find it quite easy to brutally murder everyone in Oakfield, including its guards. If you haven't already committed many foul deeds in the past, then expect to gain access to some of the more sinister titles like Desperado and Fearmonger while you lay waste to everyone in the town.

When all 37 have been slain (don't forget the monks at the Temple of Light!), return to Wicked Wilbur. He'll salute your evilness before running off to report your success to Cornelius Grim. This earns you 750 renown and the Temple of Shadows Seal. With this quest completed, you will no longer have access to the Defender of the Light quest. In addition, don't be surprised to be charged with multiple counts of murder when you return to Oakfield later in the game.