Saboteur

Originally finding their roots in espionage, the Saboteur sought out to find other methods to weaponize their profession. This lead them to a unique style of combat that involves giving the opponent harmful items without their knowing. 

Tricks of the Trade

Starting at 3rd level, you are studied in the ways of the Saboteur, granting you skill in locating enemy intel and planting false evidence. You gain advantage in Investigation checks made to locate sensitive documents and advantage on attempts to forge incriminating documents. In combat, your (Sleight of Hand) skill checks are contested by a target's perception skill check to notice your placing. If you lose the skill contest, the target evades the placement and is granted advantage on future perception checks against you until you successfully hide from the target.

If a placed item produces sound or a light effect, for each round this effect is in place the target is given another chance to notice the placement with a free perception check. Objects found in this way do not trigger the advantage on future placements by the rogue. 

Surprise!

When you choose this archetype at 3rd level, you gain a new way to apply Sneak Attack. If you successfully plant an item on an opponent and he remains unaware, the damage from the item applies the rogue's sneak attack damage. This damage can only happen once per opponent per turn. 

Saboteur's Enchantments

By 9th level, you have tinkered with enough and explored options to gain the ability to imbue objects with spell-like effects. You may choose from the following 4 effects. The act of imbuing these abilities can only be done a number of times equal to the rogue's intelligence modifier, minimum once. The saboteur regains this ability at the end of a long rest. At the time of imbuing, the saboteur establishes a trigger word to activate the effect on the items. These abilities can be triggered as a bonus action or a reaction. After the ability has been triggered or a full day has passed, the items are rendered inert.

Silence - Objects imbued with this effect create a 5 foot field of silence around the target for 1 minute. 

Truth - Objects imbued with this effect create a 5 foot Zone of Truth for 1 minute, centering on the object itself. Any person within the field has the ability to resist the effect. The DC for this spell is equal to 8 + proficiency + the rogue's intelligence modifier. 

Spike - Objects imbued with this effect release metal shards in all directions. The effect will only hit a person who has the object on their body. The shards deal 1d4 piercing damage and give the target a chancel to fail spells with the Verbal component pending a concentration check. 

Boom -  The object emits a small explosion effect, dealing 2d6 damage to the holder and 1d6 damage to any target within 5 feet of the holder. This damage type is chosen at the time of creation. Depending on the way the Saboteur crafts the item, the damage time is Slashing, Piercing, or Bludgeoning. If the object is made out of silver, the damage is considered silvered. This damage is always considered magical. Only the holder of the item can be under the effect of Sneak of Attack. This destroys the item. Due to the volatile nature of this enchantment, it cannot be enchanted onto explosive objects. Should the Saboteur attempt this, the item in question will automatically explode dealing the items normal damage. 

Battlefield Hazards

By 13th level your experience in controlling individuals has extended to the battleground you fight upon. Your experience with tinkering has granted you insight on various traps to plant upon the battlefield. The number of these items you can create per day is shared with Saboteur's Enchantments, but that number is now equal to double your intelligence modifier. If applicable, a trigger word is established upon creation. The DC of locating these traps is equal to a Hide check made by the rogue at the time of placing them. These do not benefit from Sneak Attack.

Land Mine - An explosive device made to fit into the ground. Land Mine's deal 3d6 fire damage in a 10 foot radius around the mine. Each additional land mine activated by this explosion increases this fire damage by 1d6. Land Mine's are triggered by individual command words or if someone steps into the same occupied square as the land mine. 

Net Trap - A trap containing a well-made net. This trap activates based on a trip wire, or other such similar trigger, or a unique trigger word. The trap launches a net in a 15 foot line from the direction the trap is facing. Any target caught in this net is restrained. The nets escape DC is equivalent to the rogue's current spell DC. (8 + proficiency + intelligence modifier). Only creatures large or smaller can be caught. Large creatures have advantage to escaping the net. Huge creatures and larger are immune.

Light Mines - Light Mines contain a blinding light source. This trap can be triggered by any target stepping into the same square or by a saboteurs unique trigger word. Any target within 10 feet of the Light Mine at activation is blinded until the end of their next turn. The light radiates on the field creating dim light for 2 rounds. 

Smoke Bombs - Small bombs containing a large amount of smoke. These can be triggered through a pin style activation mechanism or a unique trigger word. When activated, the bomb emits a 15 foot cloud of smoke centered on the bombs location for 30 seconds. Vision in the cloud is heavily obscured. A wind effect, such as Gust of Wind, dispels the cloud. 

According to Plan

When you reach 17th level, you have become adept at manipulating the opponents senses and going with the flow. If you are caught when placing an item on the opponent, you may feint the placement and roll a second (Sleight of Hand) check to place the item on a different location to the enemy. Items placed this way, provided the target is unaware of the new location, will proc Sneak Attack as normal.