The Humble Tailor

He will tell you, unprompted and at some length, that he is simply a tailor — that he cuts a fine suit, keeps a modest shop, and has opinions about hemlines that no one asked for. All of this is true. It is also, in every way that matters, the least interesting thing about him.

Nothing about the Humble Tailor announces itself. He does not look dangerous, because looking dangerous is a beginner's mistake. By the time a room understands what he is, the room has generally already lost.

 

POISONS (Homebrew Items — Adventuring Gear, Common, Stackable)

### Contact Poison — 25 gp

Constitution save. On a failure the creature is Poisoned for 1 minute and becomes Compromised for the duration without costing you a bonus action.

### Paralytic Compound — 50 gp

Constitution save. On a failure the creature is Paralyzed until the end of its next turn.

### Slow Acting Toxin — 75 gp

Takes effect 1 hour after administration. Constitution save; on a failure the creature's Constitution score is reduced by 1d4 for 8 hours, affecting its hit point maximum and concentration checks. If its Constitution drops to 8 or lower it is also Poisoned. It may repeat the save each hour, ending the score reduction on a success. DC 18 Medicine check to identify.

### Sensory Toxin — 40 gp

Constitution save. On a failure the creature has disadvantage on Perception checks and cannot use its passive Perception for 1 hour.

Hidden Blade

You gain proficiency with the Disguise Kit and the Poisoner's Kit.
You have advantage on any check made to conceal a weapon on
your person, and a creature searching you does not find a
concealed weapon unless it beats your Sleight of Hand check.
You can draw a concealed weapon as part of the attack you make
with it

First Contact

You have advantage on attack rolls against any creature that has
not yet taken a turn in the combat.
If you hit a creature that is Surprised, or a Compromised creature
that has not yet taken a turn, the attack is a critical hit.

The Tailor Knows His Customers

You gain proficiency in Deception and Insight. If you are already
proficient in either, you gain Expertise in it instead.
After at least 1 minute of conversation with a creature, you can
make an Insight check contested by its Deception. On a success,
the DM tells you one of the following about it: a motive, a fear, a lie
it has told you, where its loyalty lies, what makes it uncomfortable,
or whether it considers you a threat

A Perfectly Innocent Question

You may use your Dexterity modifier in place of Charisma for
Deception, Persuasion and Intimidation checks.

Something Always Survives

Once per turn, when you deal Sneak Attack damage to a creature, you may choose one of the following effects. This costs no action and no resource.

**Break Them.** The target must succeed on a Constitution saving throw against your spell save DC or have its speed reduced to 0 until the start of your next turn.

**Disarm Them.** The target must succeed on a Strength saving throw against your spell save DC or drop one object it is holding of your choice.

**Create an Opening.** One creature you can see within 30 feet may use its reaction to move up to half its speed without provoking opportunity attacks.

**Disappear.** You become invisible until the end of your next turn or until you make an attack roll, whichever comes first, and may immediately move up to half your speed without provoking opportunity attacks. You may use Disappear a number of times equal to your proficiency bonus per long rest.

Weaponized Conversation

As a bonus action, choose a creature within 30 feet that can hear and understand you. Make a Deception, Persuasion or Intimidation check contested by its Insight. On a success, choose one effect below. Once you succeed with this feature, you cannot use it again until you finish a short or long rest.

**Distract.** The target has disadvantage on the next attack roll it makes before the start of your next turn.

**Provoke.** The target must use its next turn attempting to reach and attack you, if it is able.

**Doubt.** The target has disadvantage on the next saving throw it makes before the end of your next turn.

**Reveal.** You learn the target's current hit points, its damage resistances and immunities, and one feature or ability it has not yet used.

Follow-Through

When you use Exploit the Crack, you may also make one weapon attack against the Compromised creature as part of the same reaction. If you have not already used your Sneak Attack this round, it applies to this attack.

Lingering Dose

Once per turn, when you deal Sneak Attack damage to a creature that is Poisoned, it takes an additional 1d6 poison damage at the start of each of its turns. The creature may make a Constitution saving throw against your spell save DC at the end of each of its turns, ending the effect on a success. This damage does not stack with itself.

The Name Carries Weight

After spending 10 minutes in a settlement, plane, dimension or civilization you have not previously operated in, make a Deception, Persuasion or Insight check. The DM sets the DC based on how hostile or closed the location is. On a success, choose one:

**Useful Lead** — a rumour or piece of information relevant to your current goal.**Temporary Contact** — someone who will do you one small favour.**A Secret** — something a local person of consequence would rather you did not know.**An Identity** — a plausible local cover story that will hold up to casual scrutiny.**The Weak Link** — you identify the least loyal or most compromised member of a local group.

On a failure, you still learn something — but it is incomplete, outdated or subtly wrong.

No Plan Survives Contact With the Enemy

When you fail an attack roll, ability check or saving throw, you can invoke a contingency you prepared earlier. Roll a d10 and add it to the failed roll, potentially turning it into a success. You can use this feature twice per long rest.

Terminal Application

When you hit a Compromised creature that is Surprised or has not yet taken a turn in the combat, it must make a Constitution saving throw against your spell save DC. On a failure, it takes double damage from the attack.

The Tailor Remembers

You have advantage on saving throws against being charmed or frightened, and you cannot be surprised while conscious.