|Succeeded at five difficult Persuasion attempts|
When you see a conversation option with (Persuade) before it, choose that. Select five of those end up being successful and you'll have this achievement. The four Coercion skills (Coercion, Improved Coercion, Expert Coercion, and Master Coercion) are very important for this, as is the number of skill points you have assigned to Cunning.
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