- Complete Monster: Jolly Roger was once a friend of Jack Sparrow, until he became envious of Jack's status as the next Pirate Lord of the Caribbean, and tried to kill him. Cursed to become an undead being by a vengeful witch doctor, Roger attacks towns, intending to slaughter the inhabitants and resurrect them to serve in his undead army to help him conquer the Caribbean and kill Jack. When Roger finds the protagonist with a man who had betrayed Roger, Roger kills the man after he tries to pay Roger to spare him, only allowing the protagonist to live so they can deliver a message from Roger to Jack.
- Demonic Spiders:
- Battle-Royale warships. Whenever you and your crew reach a high wanted level during a run at sea, you have a one-in-three chance of having one of these monsters come after you. As a Ship-of-the-Line, it has more health than any other enemy ship in the game (not counting the rare Treasure Fleet boss ships), and is the absolute fastest ship in the game, being able to catch up with the player from across the map in seconds. And when it catches up with you, it will kill you. How? Explosive broadsides. It can freely launch infinite amounts of the most powerful ammo in the game, with near-precision accuracy, and if your ship takes a direct hit, it will either sink or be damaged to the point where your crew will have to get to repairing immediately. Even with a good crew that can hit with pinpoint accuracy, the captain will also be working to avoid taking any hits.
- EITC Corsair ships. Like the Battle-Royales, these things have explosive broadside cannons as well, and can one-shot an un-upgraded ship with a direct hit. However, they don't have nearly as much health. What makes them a threat is their smaller size. As a War Sloop, it has a smaller hull than the other, bigger ships, meaning that your crew and broadside cannons will have a trickier time hitting it unless you can sneak up on it. It's also fast, rivaling the speed of the Battle-Royale in close quarters. If you can't defeat it fast, it will pelt you with a few rounds of explosive ammo.
- Ensemble Dark Horse: General Darkhart has been one of the most popular bosses in the game ever since weapon drops were added. It's a moderately-high-level boss, found in the doldrums of Padres del Fuego, and reaching him requires walking for about ten minutes through a cave system maze and a forest. So why is he so popular? Because he's rumored to drop Famed and Legendary Weapons at a higher rate than other enemies and bosses in the game. Some have even said that he's the only boss that can drop Jack Sparrow's Blade. It's gotten to the point where people advertise "DH Runs" in their guild chat in order to streamline farming him.
- Fridge Brilliance: Why does the main story end after retrieving the Black Pearl instead of taking the fight to Jolly Roger as the next logical step? If Jolly Roger is killed by the player, his presence during the town raids will make no sense along with the presence of the undead.
- Good Bad Bugs:
- With the addition of potion brewing came a glitch that occurred upon rapidly clicking on the same potion to drink multiple at a time. After using this glitch, the effect of the drunk potions would linger until the player logged out, instead of for the obligatory time limit. This glitch was dubbed the "Swift Foot Glitch" due to most players using the Swift Foot potion to increase their speed for the duration of their session. Unfortunately, this glitch was patched out in The Legend of Pirates Online.
- Before the Ravens Cove Story Quest was implemented in The Legend of Pirates Online, players had found an area on the island of Ravens Cove with glitched collision that could be exploited to glitch inside of the island. By swimming around, a player would be able to access El Patron's Mine, which was intended to be inaccessible at the time but was still fully created in order to prevent crashes, including the high-level enemies within. This gave medium-high level players a spot to grind without interference such as experience leeching. Of course, now that the Ravens Cove Story Quest has been added to the game - and with it, a proper way to access the Mine - the glitch isn't necessarily useful anymore, although a low-level player can still use it to enter the mine far earlier than they're supposed to.
- That One Level: Any quests that require you to face an enemy that outclasses your current levels. Hope you have powerful friends on speed dial...
YMMV / Pirates of the Caribbean Online