There are many ways to find out about this quest.

With a bit of luck you’ll learn about a boy named Aventus Aretino, living in Windhelm.

He apparently wants to hit up the Dark Brotherhood and sentence someone to death.

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Less obvious variant is to travel toRiften.

you’re free to now go toWindhelm.

After reaching the destination, locate theAretino Residencein its eastern part (screen above).

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Further action should be taken up at the night, because Aretino Residence is closed during the day.

Then proceed with your action (screen above).

Enter the residence and walk up the stairs.

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Move to AventusAretino chantingThe Black Sacrament to get to talk to him (screen above).

Otherwise you’re free to immediately take an action.

The woman should go to her chamber located in the southern part of the building (screen above).

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You might have a short conversation with Grelod, but this is not required.

Quickly leave the building.

If it is your first crime in Riften, you’ll probably make it safe.

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New primary objective: Tell Aventus Aretino that Grelod is dead

LeaveRiftenand go toWindhelmagain.

You should go now toAretino Residenceand walk up the stairs.

Report toAventus Aretinoabout orphanage’s headmistress death (screen above) and collect your reward -Aretino Family Heirloom.

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The Elder Scrolls V: Skyrim