Sinner Rogue: Crooked Moon D&D 5e Optimisation Guide

Frustrate your enemies with jinxes and immorality by invoking malefic powers.

Sinners take pleasure in the vices of the world. Drunkenness, gambling and cheating are frequent activities of sinners. In fact, they are happy to take whatever unfairly gained advantage and shortcut they can in life. This includes making deals with malefic powers. With this, they possess the ability to jinx their opponents, imposing poor fortune upon them.

Along with their jinxes, the sinner possesses a magically imbued jinx weapon (either a pistol or gaming set) allowing them to embody X Men’s Gambit with deadly card throws and dice.

I picked up the 2024 version of Legends of Avantris’ Crooked Moon supplement for D&D 5e. In this article, I’m taking a deep dive into how good this 3rd party subclass is, and how you can optimise for it.

  • Stealth class that’s highly skillful
  • Apply jinxs to your enemies to debilitate them
  • Attack with rarely resisted force damage
  • High charisma makes them a good party face too

4/5 – A solid rogue option, especially if you want to deal force damage and jinx your enemies. Your jinxes can be applied quite frequently making them a really good option. Their best feature is reserved for level 17 though, so while it is excellent, many players simply won’t hit that level of play. On top of this, throwing jinxed cards and dice is just fun.

Hex slinger (Lv 3) – 4/5

While the effects always differ, it means that you cause some kind of debuff or nullification of your target. There’s no extra action economy cost here and if your charisma is decent, you can probably use it more often than not with uses regenerating on a short rest so use plentifully.

Get jinxed (Lv3) – 4/5

Losing the loading property on a pistol isn’t as useful for rogues as it is for most martials due to their single attack anyway. It just about opens up using it for dual wielding if you have the dual wielder feat. Force damage is great though as it’s almost never resisted.

You can apply the force damage to another weapon instead, and if this is a dagger or another nick weapon, you can get 2 attacks easily through this with the force damage which is better than a single vex shot with a pistol (even with the higher damage). Ideally you want your sneak attack on your force damage (sneak attack uses the same damage type as the weapon causing it so would deal force damage too). This means you’ll probably want your jinx weapon to be the first weapon you attack with if you happen to be dual wielding.

Proficiency with gaming sets is a ribbon feature, but access to one of those cantrips is handy. Minor illusion and mage hand are great for sneaky, theft-inclined rogues. Mysterious presence is interesting as you can apply it to yourself to make yourself harder to detect. Problem is the 1 minute duration and verbal components. Out of combat, you’ll struggle to have a long enough use while speaking the spell will alert others to your presence. In combat, the action casting time is too long to want to use it for hiding. I’d avoid this one.

Borrowed luck (Lv9) – 4/5

More regular heroic inspiration is great. Using it on hex slinger is also a great way to expend it. Hex slinger is pretty good so this makes it even more available than it already was.

Pick your poison (Lv13) – 3/5

More reliable hex slinger rolls is nice and it means slightly higher sneak attack damage too. Extra damage on a double is a handy if uncommon boost and free uses of hex slinger on a 2 or 12 is another uncommon bonus. There’s a surprising number of rules to keep in mind here though so just be aware of this.

The other side (Lv17) – 5/5

Sacrifice some sneak attack damage for improved saving throws, AC and attack rolls. Often the trade off is going to make sense unless you need a large number to protect against these things. Many failed saving throws can be really problematic and successful dexterity saving throws, for instance, will mean no damage in conjunction with evasion.

Making sure attacks land is really important for a rogue and even if you knock 1 or 2 sneak attack dice off, you’re still looking at 7-9d6 of damage because you made sure you hit.

The sinner is a really solid option for a rogue. Force damage tackles a common weakness in damage type for a rogue while hex slinger creates more cunning strike-like effects which you can either merge on top or use instead of cunning strike (preserving more of your sneak attack damage).

More heroic inspiration is handy for making them more reliable and they have a great level 17 feature that makes them really resilient. A cantrip means they also have half of magic initiate with some really handy and roguish options to choose from.


Harvestborn: Avantris Entertainment
Harvestborn: Avantris Entertainment

Largely, a sinner can be optimised in the same ways as other rogues. If you want a full breakdown on how to do this using D&D 2024 character options, you can check out my rogue optimisation guide.

As this is a Crooked Moon subclass, I’ve just looked at character options in the Crooked Moon book and given advice on which work well for this rogue subclass.

Species/race

I’d consider the following species from Crooked Moon for the sinner:

  • Ashborn: Minor illusion and invisibility work well on a stealth class. Darkvision is important on a scout class and fiendish fortune is some great additional resilience that’s better than uncanny dodge (but can be used less often). Scorpion sting can’t be used with sneak attack or your jinx weapon so will rarely be a good option for you.
  • Azureborn: Flight works great for a scout and a ranged rogue. Improving initiative rolls for the party is great for anyone and guidance works really well on a skill-heavy class. Rogues already have bonus action dash, but this is a quicker version of this making it superior when you need more speed.
  • Plagueborn: Stealth proficiency, darkvision, resilience against the poisoned condition and debuff enemies with some attacks by reducing their attack rolls a little. All of this works well for rogues.
  • Relicborn: An easy option for gaining advantage is handy for a rogue and will help with sneak attacks when other options for advantage aren’t available. Aiding other’s saving throws is always handy.
  • Silkborn: A climb speed is very useful for scouting and stealth. More resilience against attacks is a good option too and it can work better than uncanny dodge. Find familiar and web are both great options and a familiar can be a good option for allowing sneak attack even when you don’t have advantage by having them stand near your target.

Backgrounds

Unlike the Player’s Handbook, Crooked Moon backgrounds give you a choice of any ability scores to increase. Based primarily on the origin feats and proficiencies, I’d recommend the following backgrounds for a sinner rogue:

NameAbility scoresOrigin featSkill proficienciesTool proficiency
CultistAnyCult initiateArcana and one otherCalligrapher’s supplies
Druskenvald dwellerAnyAnySurvival and one otherChoose one
ExperimentAnyAlteredIntimidation, medicineAlchemist’s supplies
Reflected wandererAnyUnreflectedDeception, investigationDisguise kit

Feats

I’d consider the following feats for a sinner:

  • Altered: Natural armor will always be good as it’s +1AC to what studded armor can manage. Night vision might be a good choice if you don’t already have darkvision.
  • Cult initiate: A couple of warlock cantrips and a 1st level spell can be really handy. Minor illusion and mage hand are great options for your cantrips while unseen servant can be good for stealth too or detect magic if no one else has taken this.
  • Unreflected: Hiding among people is always going to be more handy for a rogue and gives you somewhere else to go unseen (parties, soirees and busy streets).
  • Death defier: Being harder to kill is always good and the extra hit points when knocked to 0HP means you might outlast your next hit (at least at higher levels). Being tougher against death saving throws is also nice.

Interested in what else is available from The Crooked Moon? Why not check out some of our other guides?

Published by Ben Lawrance

Ben is an experienced dungeon master and player who's been immersed in the D&D universe since he was a teenager over 20 years ago. Ben is the creator of Dungeon Mister and when he's not writing about D&D, Ben loves creating fiendish puzzles and devious dungeons for his players. He's an especially big fan of the Ravenloft and Dragonlance settings.

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