If Hawke completes all available main quests in Act 1 before giving Bartrand the money for the The Deep Roads Expedition, Dougal will send a letter to Hawke which will start the Friends in Low Places quest. Upon meeting him in Lowtown's bazzar at night, Dougal will propose to loan the fifty sovereigns Hawke needs for the expedition in return for a share of the riches the expedition will uncover in the Deep Roads.
Some time later and once the expedition is concluded and Hawke arrives at his estate in Act 2, Dougal will be waiting for them as part of Profit and Loss quest. Despite being paid back in full along with interest, Dougal demands more money from Hawke. If Hawke does not pay 100, Dougal will threaten Leandra, and also say that he will spread rumours and lies about Hawke. He also reveals that he knows about what happened with Bartrand in the expedition.Hawke will always reject Dougal's demands if they do not have 100 sovereigns. If Hawke refuses to pay, Dougal will ambush Hawke in the Back Alley during a random encounter while travelling around in Kirkwall. He will refuse any attempts to settle the dispute with Hawke and mention that he could have gone after their mother but he prefers a direct approach. While signalling to attack, Dougal will mention to the Carta thugs that he wants to be in the Hawke Estate within the hour. During the confrontation the dwarf is killed and drops random loot.
- He and his men sometimes become immortal when they attack Hawke (fixed as of Patch 1.02).