From YPPedia

Players may challenge other players to a game of Swordfighting, Drinking, Rumble, or Treasure Drop, as long as the challenged player is visible to the challenging player. NPPs cannot be challenged to a game of Treasure Drop, but can still be challenged to the other games such as Swordfighting, Drinking and Rumble.

How to Challenge

To challenge a player, click on them and select the "Challenge to a Puzzle" option from the radial menu. Note that if the player has set him or herself to Do Not Disturb(DND) , you will not be able to select this option.

Next, use the dialog box that appears to select the type of puzzle, decide whether the challenge will be rated, and add in a wager, if you so desire. To present your proposed challenge to the player, click the "Issue Challenge" button. This sends your target a notification of your challenge which they may choose to negotiate or decline.

Should your proposed challenge be accepted, a second dialog appears allowing both you and the other player to further configure the challenge by editing the wager and adding items to the wager in addition to deciding whether it will be rated and what type of puzzle you'll play. You can also see what kinds of swords, mugs, or bludgeons (depending on the puzzle type) you and your opponent will be using. Once you have both clicked "Ready," the puzzle will begin. If any parameters of the match are changed, checked Ready boxes will uncheck and an alert will show next to the changed parameter. This includes changing the settings of the match and having either side change their wager or sword/mug/bludgeon.

Challenge Etiquette and Procedure

There are a ways one can keep one's challenges from being a nuisance to someone else.

• Ask for permission before you challenge another player to a puzzle.
• If a player declines your challenge request, do not issue another challenge unless they again give you permission.
• Click the "Ready" checkbox only when the challenge is configured the way you want it to be. Clicking "Ready" before you're really ready, as with a trade, could result in your having to participate in a challenge that's more advantageous to the person you're challenging than to you.
• Do not use losing a challenge as an excuse to spam, swear, or harass the person who beat you.
• Do not be a sore winner or loser. A mature pirate is one who can both win and lose with grace.