Once entering the estate, Hawke will be visited by Aveline, after which Hawke will walk into the library, where Leandra is conversing with Dougal. Despite Hawke repaying him in full and with interest, Dougal demands an extra 100. Hawke can either pay him one hundred sovereigns or refuse his extortion. Hawke will always reject Dougal's demands if they do not have 100 sovereigns.
If Hawke refuses to pay, Dougal will threaten Hawke's mother, Leandra, and Hawke by spreading fake evidence regarding the disappearance of Bartrand Tethras. At some point the dwarf will ambush Hawke during a random encounter while travelling around in Kirkwall forcing Hawke to kill him and his men (820 XP and random loot from the bodies). An aggressive Hawke can intimidate Dougal which will shake the dwarf but he will still ambush the party in the Back Alley.