Charlatan

Charlatan is a character background with skills and inspirations themed around trickery and deceit. Astarion and the hireling Kree Derryck have this background.

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You're an expert in manipulation, prone to exaggeration and more than happy to profit from it. Bending the truth and turning allies against each other will lead to greater success down the road.

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Background features

• Deception Proficiency: Gain Proficiency with Charisma (Deception) Ability Checks.
• Sleight of Hand Proficiency: Gain Proficiency with Dexterity (Sleight of Hand) Ability Checks.

Background goals

Performing certain actions that align with this background rewards Inspiration. These goals can be accomplished by any member of the active party, and Inspiration points are pooled, up to a maximum of 4. Completing an inspiration event also grants experience to characters with this background. While not necessarily all-inclusive, listed below are known events which grant inspiration points.

Location	XP Reward	Name	Description
Act 1
Blighted Village	25	Just Passing Through	Trick the goblins in Moonhaven. Using Illithid Persuasion does not work.
	25	Mirror Master	Trick or intimidate the magic mirror in the Thayan cellar.
Goblin Camp	25	Anything for a Profit	Steal the toe ring from Crusher without getting caught. Shared with ⁠What Price Dignity? and mutually exclusive with ⁠Give Them a Show.
	25	Spiked	Poison the beer in the goblin camp. Shared with ⁠Culling the Crowd and ⁠Now It's a Party!
	25	Very Important Parasite	Deceive any of the guards in the goblin camp. Using Illithid Persuasion does not work.
Grymforge	50	A Friend to All	Gain access to Grymforge peacefully by lying to the raft patrol.
Mountain Pass	30	Silver Blades, Silver Tongue	Convince Kith'rak Voss to leave without violence. Mutually exclusive with ⁠Conquer the Conquerors.
Overgrown Tunnel	30	One of Us	Use the hag's mask to peacefully bypass her thralls. Granted when a party member with the mask equipped crosses the waterfall behind the corridor guarded by the masked thralls. To protect from the effects of the mask,  Protection from Evil and Good can be used.
Ravaged Beach	20	Cheese Your Way Through	Talk your way past the bandits and enter the chapel. Must convince Gimblebock to flee and then trick Andorn to let the party inside. If the gang outside is fought, the inspiration is not granted. If Gimblebock's gang is chased off and then attacked, the inspiration is given as usual.
	20	Flexible Diplomacy	Betray the tieflings after convincing them to free Lae'zel. The party must attack the tieflings through the dialogue. If Lae'zel died while escaping the Nautiloid, this inspiration cannot be obtained.
Shattered Sanctum	25	Devil's Advocate	Interrogate the dead mind flayer without drawing suspicion.
	25	A Better Offer	Convince the pit spiders to attack the goblins. The inspiration can only be obtained with Speak with Animals active.
Underdark	30	Warmonger	Cause Glut to stage a coup - then pick a side. Report to Spaw on eliminating the duergar near the Ebonlake while having Glut as a party follower.
Waukeen's Rest	30	The Importance of Networking	Talk your way into the Zhentarim hideout. The inspiration is granted after the party convince Zarys to let them in.
Act 2
Gauntlet of Shar	75	The Devil's in the Details	Expose a half-truth in the orthon's contract with Raphael. Requires the interacting party member to succeed a passive  DC 14 Insight Check in the initial dialogue with Yurgir to detect a tricky clause in the text of the contract. Bards and Warlocks pass the check automatically.
Last Light Inn	50	Always Trust a Dishonest Person	Expose Marcus to the Harpers. Only available if Tieflings weren't saved -- if Mol is alive she will vouch for the party instead of Marcus.
	50	Not My First Time	Resist the truth serum when talking to Jaheira.[verify]
	50	Shuffling the Board	Rig the game of lanceboard.
	50	Tadpole Solidarity	Go along with Marcus' plan.
Moonrise Towers	50	Clear Conscience	Successfully lie to Z'rell about the fate of the goblins.
	60	Know thy Clientele	Instigate Z'rell into showing off her gifts from the Absolute.
	50	Pied Piper	Successfully influence the gnolls, either to break free or continue being subservient.
Moonrise Towers Prison	50	Not to Worry, I Have a Permit	Evade repercussions when speaking to the Moonrise prisoners. This can be achieved by either convincing the guards to let the party talk to the prisoners, by talking to the prisoners unobserved, or by killing all the guards and then talking to a prisoner.
Reithwin Town	60	Takes One to Know One	Expose the true form of the toll collector by removing all her gold armour. This requires killing all her minions in combat.
	60	Tricks of the Trade	Successfully pretend to drink from the steins of ale. During dialog with Thisobald Thorm, pass all three Sleight of Hand checks to feign drinking.
Shadow-Cursed Lands	75	Morally Grey	Betray the trust of Moonrise or Lastlight. This can happen in Moonrise Towers or Last Light Inn
Act 3
Multiple locations	220	Always Trust a Dishonest Person	Betray a recently forged alliance. This inspiration has multiple mutually exclusive options to gain (granted once to whichever comes first): Accept Gortash's bargain. At any point after that, if Gortash becomes hostile, the inspiration is rewarded. Enter combat against Mystic Carrion after obtaining the quest Find Mystic Carrion's Servant. Betray Nightsong to Lorroakan. Face Orin in the Bhaal Temple without killing Gortash after telling Orin that you would. Turn down The Emperor and release Orpheus.
Lower City	170	Grave Prospector	Retrieve the grave's gold from Bugthimble.
	170	Perks of the Trade	Obtain a rebate for your room at the Elfsong Tavern. Trying to persuade Alan Alyth to give a discount by appealing to the murder does not grant this inspiration. Using any other ability checks, including class-based options, do grant it.
	170	Saving a Fellow Tale-Spinner	Save Volo from an untimely death. Rescue Volo from the angry mob in front of the Steel Watch Foundry.
	170	Silver-Tongue's Better Than Any Key	Gain access to Avery's workshop. The party can either sneak in or gain access with the password obtained during Investigate the Suspicious Toys.
	170	The News of My Deeds Was Greatly Exaggerated	Rig the Baldur's Mouth printing press. Complete the quest Stop the Presses.
Rivington	135	Cheating the Cheater	Find the source of the genie's trick and take it. Pickpocket the Djinni Ring from Akabi and then win the jackpot. The inspiration is granted after Akabi awards you the "prize". Shared with ⁠A Grand Prize!.
	135	Never Trust an Honest Person	Lie to make your way into the big barn.
	135	Seams of Lavender and Thyme	Deceive your way into the circus. The inspiration cannot be gained if the party have already entered the circus' territory through an alternative route (e.g., from the Open Hand Temple). In this case, the gatekeeper Klaus behaves as if they have already convinced him.
	135	Stuffed Bears in the Closet	Blackmail the merchant.
Undercity	170	Friends in Low Places	Gain access to the Undercellar through Tusgront.
	220	Woman of Her Word	Side with the Nine-Fingers against the Zhentarim. At the conclusion of Aid the Underduke, support Nine-Fingers.
	220	Winged Serpent of Gold	Side with the Zhentarim against Nine-Fingers. At the conclusion of Aid the Underduke, support the Zhentarim. Roah Moonglow or Friol must survive and escape to the Guildhall in the previous stage of the quest.
Wyrm's Crossing	170	Not so Infallible After All	Evade being arrested by a Steel Watcher.
	170	Rock-Solid Alibi	Manage to convince the Flaming Fist to let you into Wyrm's Rock.
Wyrm's Rock Fortress	135	Nothing's Not for Sale	Convince the Flaming Fist quartermaster to trade with you.

Cut Background Goals

• Little White Lies: Lie to Arabella about the fate of her parents. Arabella can be lied to after the party find her parents, but the trigger for this inspiration event is a specific unreachable scene with Withers and Arabella.