What the achievement asks
Defeat Harlan Sweete in Freehold on Heroic difficulty or higher. Ten points, both factions.
Freehold is the pirate town on the coast of Tiragarde Sound, and the dungeon is the raid on its leadership.
The four encounters
| Order | Encounter |
|---|---|
| 1 | Skycap'n Kragg |
| 2 | Council o' Captains: Captain Eudora, Captain Jolly and Captain Raoul |
| 3 | Ring of Booty |
| 4 | Harlan Sweete |
The Council o' Captains is one fight against three pirates at once. The Ring of Booty is the fighting pit in the middle of town, which reads more like an event than a boss.
Only Harlan Sweete is named by the achievement, so what matters is reaching the end of the town.
Heroic or higher, but on one character
Blizzard's wording is "on Heroic difficulty or higher", so a Mythic or Mythic Plus run earns it just as well. There is no need to queue for Heroic specifically.
The eight Heroic dungeon achievements are not account-wide. Four on your main and four on an alt leaves you with nothing. They all have to be earned by the same character.
Once one character holds all eight, the Battle for Azeroth Dungeon Hero achievement they feed into is account-wide, so the grind only has to happen once.