Urban Adapted

At 3rd level, you learn thieves' cant, a secret mix of dialect, jargon, and code that allows you to hide messages in seemingly normal conversation. Only another creature that knows thieves' cant understands such messages. You can use this language to make contact with thieves' guilds and other underground organizations, and gather information. Thieves will naturally view you as an ally, but might still charge for their info. You additionally gain one loyal underworld contact in a city of your choice. They are the easiest for you to contact and share info easily.

In addition, any humanoid you have taken a contract for is considered a Favored Enemy. You have advantage on Intelligence (Investigation) checks made to discover information about your quarries. You can only have a number of active contracts at a time equal to your Wisdom modifier.

Finally, you gain urban terrain as a favored terrain, which grants you the following benefits:

• When you make an Intelligence or Wisdom check related to the urban environment you are in, your proficiency bonus is doubled if you are using a skill that you're proficient in.
• You cannot become lost in urban environments except by magical means
• If you are traveling alone, you can move stealthily at a normal pace.
• Even when you are engaged in another activity while traveling (such as shopping, conversing, or dining), you remain alert to danger.

Dead or Alive

At 7th level, you gain one of the following features of your choice.

Wanted Alive. If an enemy is surprised, you have advantage on Strength (Athletics) checks made to grapple them. Enemies restrained or grappled by you have disadvantage on Strength (Athletics) and Dexterity (Acrobatics) checks.

Ambush. You are at your deadliest when you get the drop on your enemies. Whenever you go first in an initiative order, you may take two actions during your first turn in combat.

Ready Minded. Whenever you roll initiative, you may replace the result with 10 + your Proficiency bonus + your Dexterity modifier.

You choose an additional option at 15th level.

Play It Cool

At 11th level, You gain proficiency with the disguise kit. Additionally, you can use Hide in Plain Sight to blend into the background of cities and towns. You can spend 10 minutes creating an appropriate disguise for yourself, putting on the persona of a common citizen.

When using Hide in Plain Sight in this way, you gain a +10 bonus to Charisma (Deception) and Charisma (Performance) checks made to avoid suspicion, instead of a +10 bonus to Dexterity (Stealth) checks. When using it in this way, you do not have to stay still, but must remain in the same general area where you first assumed your persona. Attempts to peer through your disguise are Wisdom (Insight) checks contested by your Charisma (Deception), if you are speaking to them, or Charisma (Performance) if you are acting non-chalantly. Once a creature has seen through your disguise, you lose your bonus to Charisma checks against that creature. Similarly, you lose your bonus if you draw a weapon, attack, cast a spell, begin to run, or choose to break character.

Relentless Pursuit

At 15th level, your peerless skill and ability allows you to overcome many obstacles, granting you the following benefits:

• You have gained the ability to climb faster, and climbing no longer costs extra movement.
• While at a high vantage point you have advantage on Wisdom (Perception) and Intelligence (Investigation) checks made to locate a favored enemy.
• You have advantage on Intelligence (Investigation) and Wisdom (Insight) checks to help determine the next location of a favored enemy while you are in an area they have occupied in the last 24 hours.
• You have advantage on Dexterity checks to negate difficult terrain or unstable ground, and ability checks made to escape being grappled or restrained.