Escape Artist

Sometimes, the easiest way to break someone out of prison is to get thrown in yourself. That's when most criminals call in an escape artist. These rogues are nearly impossible to keep pinned down and have a tool ready for every situation. Many escape artists have a secret workshop where they can devise new equipment and plot their next heist. Even when it looks like they're cornered, an escape artist is still liable to vanish in a puff of smoke.

Breakout Expert

Starting at 3rd level,, you know how to slip right through the enemy's fingers. Attempts to grapple or restrain you are made with disadvantage, and you have advantage on attempts to escape a grappled or restrained condition. You also have advantage on Dexterity (Sleight of Hand) attempts to pick locks made with your Thieves' Tools.

Getaway Gear

When you choose this archetype at 3rd level, you learn to craft equipment that's useful in both break-ins and break-outs. You gain proficiency with Tinkerer's Tools if you don't already have it. These tools are also added to your inventory if you don't have any. Each morning, you can use your Tinkerer's Tools to craft an amount of getaway gear equal to your Proficiency Bonus. If you have gear left over from previous days, they are dismantled to make new gear. Any piece of Getaway Gear can be thrown as a bonus action, or as part of a Cunning Action used to Hide or Disengage.

Some Getaway Gear items will force enemies to make a saving throw. The save DC for these throws is 8 + your proficiency bonus + your Dexterity Modifier.

Smoke Bombs: These are an escape artist's bread and butter. You can throw a smoke bomb anywhere within a 30ft range. The bomb explodes instantly and covers a 10ft by 10ft area. Creatures other than yourself within this area have disadvantage on attack rolls and Perception checks. You have advantage on attack rolls and Stealth checks while in smoke made by these bombs.

Caltrops: You can craft a particularly nasty caltrop with barbed edges. These caltrops can be scattered in a 15ft cone in front of you. Afterwards, the area in which the caltrops were scattered is considered difficult terrain. Creatures must make a Dexterity saving throw against your Getaway Gear DC if they are in the cone at the moment when the caltrops are scattered, or if they attempt to walk over the affected area. On a successful save, the creature is unaffected. On a failed save, the creature takes 1d4 piercing damage. This damage increases to 2d4 at the 9th level, and 3d4 at the 15th level. You cannot be affected by your own caltrops.

Bolas: Bolas are helpful tools for quickly restraining enemies. You can throw a bola at a bipedal creature of medium size or smaller within a 30ft range. The target must make a Dexterity saving throw against your Getaway Gear DC. If the target doesn't see the bola coming, they make this saving throw with disadvantage. On a successful save, the creature is unaffected. On a failed save, the creature is restrained and knocked prone. On its turn, the creature can use an action to make another Dexterity saving throw against your Getaway Gear DC to escape the bola.

Wingman

At 9th level, you've learned to modify light armor to include a wingsuit that makes for a fantastic dramatic getaway. The wingsuit gives you 30ft of horizontal movement per round while falling, reduces your falling speed to 60ft per round, and prevents you from taking falling damage. If you are knocked prone, have your speed reduced to 0, or are otherwise deprived of your ability to move, you start to fall normally, and can take fall damage. You can only have the wingsuit incorporated into one set of armor at a time.

Additionally, you've gained experience as a getaway driver. You gain proficiency in both land and water vehicles.

Advanced Equipment

Starting at 13th level, you have developed several improvements to your Getaway Gear. Each piece of your gear gains a new benefit:

Sickening Smoke Bombs: Your smoke bombs cause sickening coughs. When enemy creatures exit smoke from your smoke bombs, they must make a Constitution saving throw against your Getaway Gear save DC. On a failed save, they are stunned until the end of their next turn.

Crippling Caltrops: Your caltrops can cause enemies to lose their footing. When an enemy fails a saving throw to avoid your caltrops damage with a roll of 1 or 2, they are also knocked prone.

Black-Chain Bolas: Your bolas cling to your enemies even once they break free. After a creature escapes one of your bolas, their movement speed is halved until the end of their next turn.

Puff of Smoke

Starting at 17th level, you have learned a trick that allows you to vanish into thin air with a flash of light and a puff of smoke. How does it work? The answer is a trade secret. Once per long rest, when you are about to be hit by an attack, you can use your reaction to vanish in a puff of smoke to avoid the attack and teleport up to 30 feet away. After teleporting you can attempt to hide as part of this reaction. Creatures looking at you in a 15 feet radius around you when you use this ability must make a Wisdom saving throw against your Getaway Gear save DC. On a failure, creatures are blinded until the end of their next turn.