Monks of the Way of the Serpent value flexibility above all else, be it in mind, body, or spirit. They revere the snake for this same flexibility and aim to emulate it in their martial arts. Such practitioners excel in deflecting attacks and redirecting energy rather than simply opposing it outright. These fighters tend to favor weapons that exemplify these traits such as Whips, Rope Darts, and Meteor Hammers; and use them to control the battlefield by pushing and pulling foes, tripping their enemies, and disarming their adversaries.

Path of the Serpent

When you choose this tradition at 3rd level, your focus on flexibility leads you to master the use of certain weapons. You gain proficiency in Whips, Rope Darts, and Meteor Hammers, as well as in the Performance skill when it is used in conjunction with one of the above weapons. Additionally, when wielding a whip, rope dart, or meteor hammer; if a feature from the monk class would allow you to make an unarmed strike as a bonus action, you may instead make an attack with the weapon. If your martial arts die is smaller than the weapon damage die, use the martial arts die instead when determining damage.

Serpent's Tail

When you take the attack action with a flexible weapon, you can spend 1 ki point to forego damage and instead make a contested grapple check to attempt to push or pull your opponent. You make this check using a Dexterity (Acrobatics) check contested by the target's Strength (Athletics) or Dexterity (Acrobatics) check (the target chooses the ability to use). On a success you can choose to either push the target 5 feet away or pull the target up to 10 feet closer.

When you use your Flurry of Blows, you can replace one of the unarmed strikes with a use of this feature without spending a ki point.

Additionally, if you make a critical hit on the target you can choose to forego the extra damage to automatically succeed the above grapple check without spending a ki point.

When you reach 6th, 11th, and 17th level in this class, you can also choose to trip a target (6th), to disarm a target (11th), or to swap positions with a target (17th) when you succeed in your grapple check.

Serpent's Strike

At 6th level, you extend your ki into your flexible weapons, granting you the following benefits.

Magic Flexible Weapons. Your attacks with your flexible weapons count as magical for the purpose of overcoming resistance and immunity to nonmagical attacks and damage.

Deft Strike. When you hit a target with a flexible weapon, you can spend 1 ki point to cause the weapon to deal extra damage to the target equal to your Martial Arts die. You can use this feature only once on each of your turns.

Serpent's Tail

When you reach 6th level in this class, you can trip a target with a successful grapple check using this ability. The target is knocked prone.

Serpent's Dance

At 11th level, your mastery of flexible weapons grants you expertise in the Performance skill when it is used to perform with a flexible weapon. Additionally, when you take the attack action and target an item or creature, you can use your weapon to throw the target (if it weighs no more than 10 lbs) at a different target within 30 feet. You use your martial arts die for the damage roll. If you target an object or creature large enough or fastened in place, you can instead pull yourself 10ft closer to the target.

Serpent's Tail

When you reach 11th level in this class, you can use your Serpent's Tail ability to disarm an opponent on a successful grapple check.

Serpent's Cunning

At 17th level, when you are targeted by an attack that targets only you, you can use your reaction to make an opposed grapple check against the attacker provided they are within range. On a success, you can redirect the attack towards a different target within range, or cause it to miss harmlessly. This ability does not work on creatures more than 1 size larger than you.

Alternatively, you can use your reaction to target an object within range to pull yourself out of the way. To do so, you need to pass a reflex saving throw with a DC equal to your opponent's attack roll and must have at least 5 feet of movement left when you ended your previous turn.

Serpent's Tail

When you reach 17th level in this class, you can use your Serpent's Tail ability to swap positions with a target on a successful grapple check. You must have enough movement remaining to reach their position and they must be within reach of your weapon. This ability does not provoke attacks of opportunity.