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The Elder Scrolls V: Skyrim Hints
Talk to Ranmir about Haran.
1 of 4: Go to Winterhold and find the woman named Haran in the Frozen Hearth inn (or its cellar). Ask her what's wrong with Ranmir, then offer to talk to him. (If she doesn't have that dialogue option, try again later. It seems to come up more often when she's in the cellar.)
2 of 4: Find Ranmir in the inn's main room, then tell him that he needs to pay Haran back for all of his drinks.
3 of 4: Try the persuade option first. If it fails, either bribe him or beat him in a brawl. (Note that you may have an intimidate option instead of a brawl option.)
4 of 4: After optionally giving him a drink from your inventory, return to Haran and tell her that Ranmir's agreed to pay his debts. She'll give you a leveled weapon and armor as a reward.